BOS - CHI

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BOS — CHI
Oct 5 — Oct 121
Round-trip
1 adult
Economy
0 bags
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Wed 10/5
Wed 10/12

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Good to know

Low season

January

High season

June

Cheapest flight

$69

Average price round-trip

$221

Good deal round-trip

$186

Good deal one-way

$109
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 33% increase in price.
Flight from Boston Logan Intl to Chicago
(avg. price over the last 2 weeks)
or less
or less

When to book flights from Boston to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight out of Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $109 or less one-way and $186 or less round-trip.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is January.
  • Morning departure is around 24% cheaper than an evening flight, on average*.
  • Consider booking flights with at least a single stop en route if you want to fly more affordably from Boston to Chicago. These flights have different stopover options depending on your airline and arrival airport. Spirit Airlines, American Airlines, and Delta have common stops in Philadelphia, Detroit, Myrtle Beach, Washington, and LaGuardia Airport.
  • Flights from Boston to Chicago arrive at either O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Of the two, ORD stands out as the best airport to fly into. It serves most of the direct flights from Boston and also has good connections to various transportation forms.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can steam off before catching their flight. They are near Gate 18 in Terminal A, and by Gate 25 in Terminal C. In Terminal B, they are between Gates B30 and B36.
  • If you need cash before flying out from BOS, visit the ATMs at the airport. Citizens Bank, Chase, and Bank of America operate ATMs in the Departures area in Terminal A. ATMs are also available in various locations in Terminals B, C, and E.
  • Passengers flying to ORD are welcome to use the charging stations at the airport. You can find the charging stations by Gates B19, B15, B14, B11, and B4 in Terminal 1. In Terminal 2, you will find the charging ports by Gates C28, C21, C15, C7, E7, and F2B.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal's Test Kitchen. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport, this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
  • There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
  • Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at BeRelax? Located in Terminal C near Gare C-25 at Boston Logan International Airport, BeRelax also offers waxing and facial care to give you your best look and most relaxed self before your flight.
  • Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
  • When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access, and even a Starbucks coffee shop.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking flights from Boston to Chicago

Top 5 airlines serving Boston Logan Intl to Chicago

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 20462 reviews
8.2Boarding
8.2Comfort
8.5Crew
7.9Entertainment
7.7Food
Airline reviews

Because flight delayed 2 hours and I have make change on my plan I have to waste my time I am not happy with it. I am not recommending this airlines for my family and friends.

Read more about JetBlue

Because flight delayed 2 hours and I have make change on my plan I have to waste my time I am not happy with it. I am not recommending this airlines for my family and friends.

Cons: "Nothing... great flight, uncrowded flight, plenty of extra seats to stretch out. Seat were very comfy and spacious which I loved even got a full can of soda unlike the usual half a cup and done lol. Would definitely fly Jet Blue again and prefer also. Way better than the other carriers."
Pros: "MINT CLASS is amazing"
Cons: "The headphone jack.was worn out, so the audio was sporadic."
Cons: "Flight was very delayed, waiting on pilots to arrive. The. We sat on the runway for a long time without leaving as well. Crew also made us gate check bags when there was still plenty of overhead space left on plane."
Pros: "crew was great."
Cons: "flight was 3 hours late with lame excuse. tray tables disgusting. felt unclean. cookies tasted gross. pa system not working. live flight not working either"
Cons: "Horrible communication during flight delays and pilot timing out. Sat at the gate for hours with no communication."
Pros: "Crew was great, seat very comfy with good legroom."
Cons: "Two hour delay between boarding and then sitting on the runway."
Pros: "The seats were comfortable, and the crew was friendly."
Cons: "Entertainment units were just there for the sake of it, and didn't actually provide any entertainment"
Cons: "JetBlue is amazing and my favorite airlines for domestic travel."
Pros: "Not too full of a flight"
Cons: "It was delayed 3 hours"
Pros: "Plenty of leg room in economy seats."
Cons: "clearly communicate delays. We had no idea what was happening or what our options were."
Pros: "Crew was very nice."
Cons: "Tv did not work on a 4 hour 40 minute flight."
Pros: "Boarding was fast and easy but that may have been because it was a small plane."
Cons: "After landing we sat on the tarmac for 2 hours! This is unacceptable. The gate was occupied by a plane having mechanical issues. This was the second time I have flown JetBlue and the second time I’ve had to sit on the tarmac for hours because of some sort of issue. Never flying JetBlue again if I can help it."
Pros: "Crew was nice. legroom seemed a little better than other domestic flights."
Cons: "You have to pay extra to sit in the exit row and there was no one in the entire row. Isn’t that a safery issue? Also, what really made me mad, instead of printing our boarding passes at the kiosk we went to a person (husbend had questions about Precheck) and she made us buy return tickets right then, on JetBlue. We had not decided on our return and wanted to leave it open. Can she do that? If not, I would like my money back."
Pros: "The movies were okay. The crew was accommodating."
Cons: "We spent 45 minutes on the tarmac, enough time to watch the baggage personnel throw our bags into his trolley with zero reason for him to do so. If you pack anything fragile... good luck."
Pros: "Easy boarding and flight"
Cons: "There’s nothing special about jet blue anymore."
Cons: "The new security check in with the automated bins."
Pros: "Huge leg room in coach. Free large bag of snacks and they didn't charge me for a snack box filled with chumous, bean dip, crackers, biscotti etc value $9. I thought Jet Blue was like Spirit, but its TOTALLY different. Not at all a budget level airplane or crew."
Pros: "Extra leg room, comfortable, leather seats, cleanliness of the cabin, efficiency and friendly manner of the staff, assigned seating and enough room in the gate area to be comfortable. I also appreciated being able to hear and understand all announcements made in the gate area and on board by the support staff and the captain."
Cons: "Some passengers in the gate area were "seat hogs" sitting in one seat and taking up one to two extra seats for their baggage while people were trying to find places to sit, especially when we experienced delays.. This is not the fault of the airlines, however, but it occurs to me that there could be gentle reminders on in print or in announcements asking people to make room for other passengers."
Cons: "2 hr delay. Poor ventilation"
Pros: "Leg room was great. Free WiFi and TVs made the flight very accommodating."
Cons: "Crying baby. Not the airlines fault."
Cons: "Flight over 3 hours late leaving. Flight attendants rude, and nothing comped for drinks or food to make up for it. Had to circle for 45 min due to weather. Sat on tarmac 30 mijn on other end."
Pros: "Having a tv"
Cons: "Sound jack not working properly , older plane no amenities"
Pros: "The crew could not have been more helpful and pleasant making the delay bearable as they were overtly communicative w all via text, email, and in person keeping is updated! HIGHLT RECOMMEND and will definitely be flying again. :)"
Pros: "Great service and smooth flight. On time, all good things."
Cons: "An individual who was very overweight sat next to me and took up half of my seat as well. I understand we all deserv to ride comfortably and my intent is not to shame them. That said, if someone can’t put the armrest down I think the airline should require them to purchase both seats as it’s very uncomfortable to be in the position of having no seat for the entire ride. I’m an average sized person so it was a challenge but even tiny people deserve the full seat they purchased. There really should be a rule or something."
Pros: "Wide array of snacks and drinks, tv/movies to watch for free, excellent staff from beginning to end, and tons of legroom. The complimentary free check of my carryon way awesome."
Cons: "I liked everything! No complaints at all."
Cons: "Six hours late, then there wasn’t enough fuel and had to wait for paperwork multiple times. Hands down the worst experience I have ever had. I will not be flying JetBlue again."
Cons: "Almost a 9 hour ordeal. 4 hour delay because of weather for flight because one crew that was supposed to take our flight had “timed out.” Didn’t take off til after 1am. Finally landed and sat on plane because a plane at our gate was “disabled.” It’s 4:33am, I’ve been off the plane for half an hour, no baggage coming out of the carousel yet and no sign of this absolutely horrific experience ending anytime soon."
Pros: "Loved all the available dedicated JetBlue staff available to answer questions. Have not flown JetBlue often but heard many great things."
Cons: "Weather delay which is out of JetBlue’s control but once we landed (6 hours later) we sat on the runway for an additional hour because our gate had a disable airplane occupying it. I think JetBlue could have done a better job ensuring a back up gate was available or giving their passenger updates on the situation."
Pros: "The leg space"
Cons: "Delay and the space between seats"
Cons: "I never got the opportunity to fly because I was stuck in unusual traffic in a tunnel for over an hour just minutes from the Boston airport. I was later told there was a fire. I called the 1-800-JETBLUE number and I explained that the situation. The agent said that there would be a $75 change fee and at 4:47 pm there were no more flights out that night and that I would also be charged the fare differential the following day. I quickly went on line and found a deep discounted fare on United for $56! When I got to the airport there were several other people with the same situation. Not a enough agents on staff and no concern that I might miss my new flight on United. Thank Gid I acted fast and got another flight that evening or I would have needed to spend the night in the airport like a woman and her mother traveling to San Jose! Need more professionalism !"
Pros: "everything was good except that I didn’t like to pay for blanket"
Cons: "to pay for blanket"
Pros: "JetBlue has great staffdelayed by an hour"
Cons: "Delayed by an hour for a 2 hour flight!"
Pros: "When I got off the plane"
Cons: "it was late, the plane was dirty, the tv screens didn't work, and the seats were small."
Cons: "Normally I love Jet Blue but we were delayed first for three hours. The only reason I even knew was because I asked someone if I was at the right gate because it didn't state it was a JetBlue gate anywhere. Then we were delayed two subsequent times for a maintenance issue and a gas issue. That didn't inspire any confidence whatsoever. We were also told we would be receiving a flight credit which I have yet to see."
Pros: "Plane departed early and arrived 40 minutes early. Well done"
Cons: "Prefer BLUE Chips rather than cheese x AND usually they call for VETERANS to board before the start of general boarding. This is the first time Jet Blue DID NOT extend that courtesy"
Pros: "Quick and on time"
Cons: "My seat did not go back, and sitting upright the entire flight was very comfortable. When I asked the fight attendant about the seat, he said seats do not go back forward of the exit row. Had I known this, I would not have booked my seat. This information was not made clear to me when I arranged the flight. I am looking to book another flight R/T from Boston to NYC and would appreciate compensation for this upcoming flight."
Pros: "leg room & movie"
Pros: "Seats were comfortable (an Airbus A320). Entertainment system adequate. Smooth flight."
Cons: "Two dogs in cabin. They were mostly well behaved. A group of six children loosely supervised by a couple of adults. The children were allowed to wreak havoc on the center section of the plane's cabin."
Cons: "Late flight delayed"
Pros: "Boarding, crew, bathrooms, entertainment, smoothness of flight, wifi"
Cons: "Always hope for more than water and pretzels, but those days are gone I guess."
Pros: "Most of the basics were good."
Cons: "The flight was substantially delayed and when we got to Chicago we had to wait a long time for a gate agent so that we could deplane because only one gate agent was working at that hour (10:20 p.m.). Also, the flight delay notifications came after I was close to the airport and at the airport--earlier notifications (if possible) would help. The tv/movie portion of the entertainment was not working at all."
Pros: "Changed to 3 hour earlier flight WITHOUT extra "change fee". It was FREE !! Enjoyed in flight TV with FREE drinks and snacks. As United goes backwards in customer service and costs, JetBlue leaps forward. Good work JetBlue."
Cons: "More options in snack boxes and/or food items"
Pros: "The plane arrived safely in DC."
Cons: "I didn't like that the flight was delayed but it's understandable."
Pros: "Solid crew, comfortable flight, free tv and Wi-Fi"
Cons: "A few factors led to a 6 hour delay. Not necessarily Jet Blue's fault but it was certainly a frustrating day of travel"
Pros: "The plane had 2 wings"
Cons: "Staff is rude. Customer Service couldn't possibly be worst. All their food has meat in it. Staff is slow and incompetent. Never had a more dreadful experience with an airline. TAP IS THE WORST AIRLINE I HAVE EVER EXPERIENCED, and I fly 2 times a month."
Pros: "The on flight tv was down so I couldn't listen to music like I nearly always do on my flights."
Cons: "I didn't like waiting on the tarmac after we landed for what seemed like 25 minutes or so"
Cons: "Top carrier"
Pros: "The crew was great. The pilots too."
Cons: "The audio and video at my seat did not work correctly."
Cons: "The flight attendants were fantastic!"
Pros: "Well organized and easy to check in."
Cons: "No"
Pros: "Delayed boarding but made up for lost time in the air"
Cons: "Delayed boarding"
Cons: "No mechanical failures or delays would be nice"
Pros: "Was boarded promptly"
Pros: "Entertainment. Flight attendants. Food"
Cons: "PROBLEM WITH LOCATING BAGGAGE CAROUSEL. GIVEN WRKNG LICATION ."
Pros: "this is the airline"
Cons: "Better allergy aware food."
Pros: "Crew was amazing. Pilots were attentive to kids and answered questions. Everyone was very welcoming and helpful."
Cons: "They didn't have some of their food options (and they apologized for that up front), but then ran out of the others by the time they got half way through the plane. That was tough for a five hour flight that went through dinner time."
Cons: "Wonderful"
Pros: "I love ice cream and chocolate"
Cons: "Healthy vegetarian meal choice"
Pros: "Seat was hard, not much foot space"
Cons: "My wife and Iasked for a snack, it was never delivered"
Pros: "Good entertainment options."
Cons: "Only water and coffee available. Flight had been delayed over an hour."
Cons: "Crew didn’t serve drinks/snacks; otherwise nice and short flight"
Pros: "N/a"
Cons: "The crew members were very rude and they called me an IDIOT!! Yes they did because the forced me to check my carry on bag and i didnt want they are racists"
Pros: "Crew was friendly"
Cons: "An hour and a half late, terrible communication about scheduling"
Pros: "Good flight in air"
Pros: "The seat get’s bit hard after 14 hours."
Cons: "The food was ok but not great"
Pros: "Smooth flight."
Cons: "Tight seat. Small space."
Pros: "Overall service was great."
Cons: "Flight was delayed 5 hours."
Pros: "wonderfu crew... very helpul`"
Cons: ".."
Pros: "Everything went great. Flight left a little late but was fine and only arrived a little late. I like the side wings on head rests really help."
Cons: "Seats are always hard on long flights."
Pros: "Nothing"
Cons: "Flight was horrible"
Cons: "Flight delayed by 2 hours- was just sitting in the plane for couple hours before it took away"
Pros: "Plane was on time."
Cons: "My seat assignment was in the last row of the plan when the plane was not full"
Pros: "Leg room and seats are very tight and I'm a small person."
Cons: "Coach class is very crowded."
Cons: "insufficient overhead luggage space"
Pros: "The woman who helped us at the desk by the gate was possibly the single most helpful, kind Delta employee I’ve ever met. She wheeled me down the jetway and upgraded our seats. I wish I knew her name. She has very curly dark blonde hair and is petite."
Pros: "The staff. They were very helpful and polite!"
Cons: "We didn’t leave on time"
Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"
Pros: "gate staff were great"
Cons: "plane cabin staff looked overworked"
Pros: "Delta flights run one time and their fleet seems newer than most with comfortable seating. Having free movies in the seat back ahead of you is a big plus with a good selection of movies. Snacks are good and crew is always friendly and accommodating. We fly almost exclusively with Delta for the aforementioned reasons."
Cons: "Boarding is a hassle no matter the airline with few exceptions. You would think someone could figure and efficient method to get people on the planes. I suppose it could be the public that is the problem. Not a problem with Delta they run a good airline."
Pros: "the service in general very nice"
Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."
Pros: "Nice people. Very helpful."
Cons: "LOST MY BAG IN BOSTON BEFORE EVEN TAKING OFF!!!! Did not make it, and then won't deliver it when it makes it to Kathmandu! This is most distressing."
Pros: "Movies"
Cons: "Not supplying headphones Crew not to helpful, one unpolite Refreshments ridiculous"
Pros: "I was thankful for the early boarding with a lap infant and was very pleased with the options for entertainment on the TV monitor."
Cons: "The main issue I had was that we sat in row 34 and the noise from the engines often made it difficult to hear announcements, even with headphones in. Look into possibly zoning the audio and turning it up a click or two for rows behind the engines."
Cons: "Missed our connection. Spent the night in Minneapolis. Luckily we had no urgent reason to get home to."
Cons: "Jet airways sucks"
Pros: "Free first checked bag, comfy seats"
Cons: "Would have liked more movie selection"
Pros: "The only flight that was a bit better was from Mumbai to Hyderabad."
Cons: "Almost the entire trip, due to the following reasons: 1. The online check in process didn't work at all. The Delta staff at the Boston airport weren't pleasant and courteous at all. 2. Poor coordination between Delta & Jet Airways - the meal preference was selected before flight at the Jet Airways website but the same didn't get registered properly, even though the website confirmed to me that it was all set. This resulted in appropriate food not being available to the customer on the flight from Boston to Amsterdam. The customer had to literally starve on the flight. 3. The pursers and stewards on the flight from Boston to Amsterdam weren't pleasant and courteous at all. For anything they were asked, their responses ."
Pros: "It only took them 10 minutes to turn things around to make up time for the delay."
Cons: "The seat pockets were not cleaned."
Cons: "Not having a seat assignment until arriving at the gate."
Pros: "The entertainment system worked well and was able to keep my phone charged."
Cons: "It's very cramped seating. They started boarding by rows but then gave up. Crew are nice."
Pros: "Nothing."
Cons: "Reservation. Checkin. Seating. Flight."
Pros: "arrived early"
Pros: "The crew was friendly and boarding was easy."
Cons: "didn't provide snacks. They took a long time to retrieve the luggage that was checked at the gate."
Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Awful awful awful Got an email notification in the middle of the night that flight was delayed and that we would miss our connecting flight so we scrambled to get seats moved. THREE HOUR WAIT for customer service.

Pros: "Im usually not one to sleep on ttransport but I was very comfy on this flight and was able to sleep the whole three hours"
Cons: "The snacks."
Cons: "Great flight, ontime departure and early arrival. Bags were delivered within 15 minutes of Ariosto the gate."
Pros: "Easy no hassle check in and board."
Cons: "Absolutely nothing. Thank you!"
Pros: "My legs were sandwiched behind the seat in front of me. I hate that kind of seat spacing."
Cons: "The crew was outstanding and the aircraft was new and comfy"
Cons: "The airport experience was horrible. American Airlines did not have enough personnel on duty to process all the waiting passengers."
Pros: "Plane left and arrived on time. Otherwise uneventful, which these days is good."
Cons: "Others got I choice of snacks. I just got a cookie."
Pros: "Flight attendants were two hours late"
Cons: "Baggage claim number was wrong. They almost took my bag away"
Cons: "Boarding at Heathrow is horribly inefficient."
Cons: "If I actually made my connection. Delayed flight out of Boston"
Cons: "The security check line was about a mile long at the Terminal 1, but that's not the airline's fault."
Cons: "There was no entertainment at all, and pretzels are gross"
Pros: "Nice plane and entertainment"
Cons: "Booked flight through British air for a reason. Didn’t anticipate American Airlines being used for our flights. The Flight was also delayed but it was never explained why despite dozens of questions from passengers. This caused a missed connection flight and forced us to stay overnight in Chicago with nothing but a $12 food voucher. When we tried t ask what other options were, American Airlines personal offered no sympathy and said the best we would get is the food vouchers and we should be grateful. No other travel reimbursement or vouchers were offered other than a replacement flight. Overall it was a huge inconvenience and caused numerous other expenditures for us."
Pros: "Landed safely and on time. Crew was nice."
Cons: "Cramped. Older plane missing USB plugs. Entertainment requires an app. Bathroom door still has ashtray. Should have been cheaper for what I got which was a regular ticket for a 5'8" 160lb person."
Pros: "Boarded early and landed early."
Cons: "Gogo WiFi didn’t work"
Pros: "Best landing I’ve experienced recently!"
Pros: "The flight attendants were really attentive and came to our rescue. In flight entertainment was good."
Cons: "Americans airlines charged me extra to guarantee that my wife and I, along with our infant daughter could sit together. Of course with this came the expectation that we would at least have more leg space. Which we did not. Go figure."
Pros: "One cabin crew went the extra mile for me...rescued a partial dental plate which I had inadvertently tossed in the trash."
Cons: "Terrible turbulence"
Pros: "Was supposed to leave at 8:00 am. Waited for 4 hours, got my flight rebooked after having to search for an AA representative. I had to get my luggage due to the change of airlines, after waiting for an hour at the luggage reclaim center i was told that my bag had already shipped by itself with other flight"
Cons: "Everything. Poor service. 5 hours of waiting. Disaster"
Pros: "No food, no entertainment. Flight very smooth. No legroom"
Cons: "No legroom. They made me check carry on"
Pros: "Direct flight, sketchy weather but we arrived pretty close to “on time”"
Pros: "I like the cookies. Any flight that safely lands is a good flight. I didn't have to hear the inflight "entertainment". There was room for my backpack, and I was in group 6 on a nearly full flight."
Cons: "I hate having media flashed in my face. The srewardesses misses me when serving beverages, which is hard to imagine, and rarely happens. We had a particularly bumpy landing. I've flown a fair amount, and I thought our bouncing and jostling was unusual, but then weather is unpredictable - still... I've seen navy pilots stick landings of small planes in worse weather."
Cons: "Delayed flight, multiple gate changes"
Pros: "Everyone was so friendly and helpful, especially Ricardo at the check in desk. Our flight was delayed for 2 hours but the friendly staff made it easier to deal with the delay!"
Pros: "I would like if for my return from Paris to Chicago, Chicago Seattle I would be greeted by the personal and offered to flight first class without extra charge to compensate for the bad experience on my way going in. Thank you"
Cons: "I was told I would be able to choose the seats only 24 hours before the flight by going online. I tried to choose the seats online but could not have access to the site. I then called the number provided to ask for more help, and was told that I could then only choose the seats at the check in time. I was at the airport 2 hours before the flight schedule to book my seat and was told them that I could only choose the seats at the gate. Once I got at the gate I asked the person to please give me a seat at the aisle for medical reasons but after waiting until the boarding process had started I was giving a middle seat. Not only I was treated as a stand by passenger that had not purchased the tickets I was put nt on group 8 and at the moment of boarding the gate personal aggressively grabbed my carry-on bag because they insisted there was no more spaces in the compartment above heads. Once I got inside of airplane I saw many empty compartments available for carry-on luggage. I wish I had not purchased my ticket with Iberia Airlines operated by American Airlines. It was not a good, pleasant experience and do not recommend. I wil certainly avoid in the future and not travel this way another time. Thanks"
Pros: "Full flight, crew worked timely"
Pros: "Crew was nice, biscuits were nice"
Cons: "crammed like sardines, if you're over 5'6" You charged extra to get a little more leg room and if the roomier seats are sold, you're out of luck."
Cons: "Seat 20f It was very uncomfortable and freezing My legs were sore after the journey. Besides until 30 seconds before actual boarding time the members didn't inform about the delay. Everybody had formed lines and we see people getting out only then."
Cons: "I do not like that I am missed my flight and got stuck in a city without any re-embersement. I usually use United, but decided to use American Airlines this time. Sleeping in an airport tonight. Thanks."
Cons: "After everyone boarded they said they had a 2 hour delay and if you got off the plane your flight would be cancelled. After an hour of sitting on the plane they got everyone off so a different plane could board and take off and then everyone got back on the plane and continued to wait. We left 2.5 hours late and when we arrived at the destination the plane couldn't contact the tower?!?! So we waited another 30 mins...ridiculous, rude, and rather fly southwest"
Pros: "Flight was on time"
Cons: "There was water dripping from the vents. When I tried to inform the flight attendant, she shut me down so fast I couldn't believe it. All she had to do was reassure me that it wasn't a safety issue. Her attitude was like she was tired of telling passengers that it was perfectly normal. Very unprofessional!"
Cons: "Lots of time changes. 1 piece of luggage sent wrong destination."
Cons: "Delayed 3 hrs and then sat on runway upon arrival at ohare. I was forced to check my rollerboard even though I've fit it perfectly in the overhead compartment just yesterday on my previous flight (also American airline)."
Pros: "The flight crew were great, attentive and accommodating. There were empty seats which allowed for movement of passengers and some stretching out during the long flight."
Cons: "The only issue was one restroom not functioning, which caused a line to queue throughout the flight for the working restroom. Otherwise no complaints."
Cons: "Paid for extra legroom, got a seat that didn't recline :("
Pros: "Courteous crew"
Cons: "The plane was tiny and old"
Pros: "flight personal were very nice"
Cons: "Seat broken reading light did not work 15 total hours in the air and 7 of them the movie system did not work Paid for upgraded seat and did not get one - got moved to a standard seat."
Pros: "The stewardess was nice enough to give me water with my gingerale"
Cons: "We didn't take off until 3 hours after scheduled, and we're forced to watch ads on the overhead monitors for most of the flight. I was not impressed. Poor communication from the pilot."
Cons: "Would at least like a choice of a snack instead of cookies I don't care for."
Cons: "The fact that people carry-on luggage that exceeds the max requirements for carry on luggage so they can avoid the checked luggage fee. It's a disgrace. It time to live by your rules, the same for everyone. I had to be rebooked out a different airport as PGV was flooded. I was seated in 21F which does not recline. AA cancelled my flight out of PGV, a better seat would have been nice since I had to drive an hour to EWN whereas I was staying only 10 mins from PGV."
Pros: "The in-flight entertainment interface was well-designed. The aircraft tracker is the best, the media selections were plentiful. Having the usb and headphone plugs next to the monitor is the best. Better than Virgin for sure. But strangely, you couldn't order from the food and drinks menu like you can from Virgin so it was just a video version of the menu card. Food was good."
Cons: "Someone destroyed a lavatory so we were short one for the flight and caused a 30 minute delay before take-off. The usual spiral happened: pilot flew into bad turbulence to make up time. No biggie."
Cons: "I was supposed to be there right now, but I'm still waiting in Chicago for my connecting flight to Dayton that was delayed."
Pros: "personal entertainment systems and charging plugs"
Cons: "only pretzels and no headphones offered for the entertainment systems."
Pros: "Seat were comfortable and I didn't feel claustrophobic."
Cons: "Being stuck in a high dollar city for an additional night when i should have made it to the lower intermediary city and flown standby the next day."
Pros: "The cookies were good"
Cons: "The gangplank was broken. It took so long for them to ascertain the situation, move the broken gangplank away, move the plane from gate B15 to B16, load passengers & luggage and take off, that I missed my connection in LaGuardia. I had to get a standby flight & thankfully got on. Why wasn't that equipment checked out long before it was used?"

No food, no comfortable seats but at least staff was decent.

Everything was great!

More leg room

The seats are small and hard. There are zero frills whatsoever. Everything you can think of costs extra. Beyond that we were surprised at how uneventful and easy the flight was. We only spent 3 hours on the plane (Boston to Florida), if it were more than that I might look elsewhere for a bit more comfort...

Pro- The flight was on time Con- seats were uncomfortable, person sitting next to me took up 1/4 of my seat. If the arm rest was more substantial it would divide the seats more equally. At Rockford Airport baggage took too long to come in

Worst airline experience of my life. Do not recommend. News flash: allegiant has never heard of connecting flights. You’re dumb enough to take two allegiant flights on the same day? Well, buddy, get off the plane, race to baggage claim, wait forever, haul your bags to the ticket counter, pay another baggage fee, then get your sweaty butt back in that security line and figure out what to do about the flight you missed. Because allegiant does not check your bags to your destination. It’s their policy. No joke. If you catch a connecting flight, your bags will not. That’s just the allegiant way!

Tried to check in on line and I could not do it. Because I had minor kids with me. We were separated in our seats. I had to pay airport prices for my bag going back to Rockford I was not a very happy camper.

This flight not too much to like. .5lbs and they were gonna charge us $50. No one on the flight had a personality. Literally they all just stood there with a frown on their face. My 3 year old who is always cheerful spoke to all the ladies and they all just said hi in a somber tone. Very disappointing. Got charged for two drinks when paying with my Allegiant Mastercard. Should have gotten one free. Just a disappointing flight experience.

Flight was cancelled because they didn’t have a plane. Waited in the airport for hours after being delayed 4 hours initially. Had to drive 15 hours to Florida. Never flying Allegiant again and will never in a million years recommend this poorly constructed airline.

Pros: "The direct flight is amazing. The status updates were great. The crew was super friendly."
Cons: "Not much, it was great. No more masks for vaccinated people would be awesome."
Pros: "Nothing. Worst flight I’ve ever taken."
Cons: "We were on the tarmac for 3.5 hours with little communication or apology. The seats were very uncomfortable. Terrible turbulence. Not even a complimentary soda for all of this. I will never fly Allegiant ever again."
Pros: "Crew was great!"
Cons: "Boarding was excruciatingly slow."
Cons: "Give complimentary water"
Cons: "Major delays, no communication from airline"
Cons: "Temp in the cabin was a little chilly but not totally uncomfortable"
Pros: "Quickness, efficiency"
Cons: "Nothing. I received all I expected."
Cons: "The padding on these seats."
Pros: "This crew was amazing"
Cons: "The seats are very hard."
Cons: "If you dont have TSA precheck....get it...lifesaver"
Pros: "Crew nice. Seat okay"
Cons: "Entertainment"
Pros: "Flight attendants were very kind, attentive and caring. There was a special needs girl in the same row as me that was by herself and they were always making sure she was okay and comfortable as well as the rest of the plane."
Pros: "FLIGHT TIME"
Cons: "NOTHING"
Pros: "Comfort nice cool cabin on boarding"
Cons: "No complaints with airline but flight was a little ruff on approach made me a little nauseous."
Pros: "Nice pilot and crew."
Cons: "The warning about alcohol was a bit sarcastic, but I guess in today's world people who have acted out are the real culprits..."
Pros: "loading was smooth, departure was a bit early, arrival in Cedar Rapids was about 30 minutes early!!"
Pros: "The crew was friendly and the price was low."
Cons: "Communication during our delay."
Pros: "The check in was fast and painless."
Cons: "Delays!!"
Cons: "The flight was delayed all day!!!"
Pros: "Yes"
Cons: "Flight was delayed 6 hours."
Pros: "It is hard to beat the price of tickets for this airline. I love the price; that the flights are direct & almost always on time; that the staff, from the flight attendants to ticket agents, all seem professional, helpful & friendly; and that the planes are clean and seats well cushioned & comfortable."
Cons: "I don't like that the seats don't lean back & that they are very close together with little leg/knee room. Altho the base price for the flights is cheap, they charge for "extras", including making your reservation by phone instead of online, printing out your boarding pass &choosing your seat. There's a fee for carry on's as well as regular size luggage. If you don't prepay for your luggage or if your luggage weighs more than 40 lbs, they charge $50, instead of $25. They not only charge for food, but also for water or any beverage. If you are prepared for a no frills flight & are willing to sit separately from your travel companions, etc. then this is a great way to save time (direct flights) and money. I will choose to fly with them again, even tho My husband & I prob. won't get to sit together. If you know what to expect & plan for it, it is a great way to save."
Pros: "The staff and crew are extremely polite and focused on good service."
Cons: "The seats on the Allegiant MD-80 don't recline AND the space between one row and the next is EXTREMELY tight. Much tighter than I have seen in an airline in a while."
Cons: "Boarding process"
Cons: "Seats are uncomfortable- they do not recline and the springs in the seat back pole into your back"
Pros: "Friendly staff"
Cons: "Last minute delay due to a plane malfunction. Was told very last minute. Seemed like there were no quick resolutions in play. Had to wait over three hours to fly out, doesnt that entail compensation by law?"
Pros: "It got us there and back for a descent price. The flight was fine but the seats are not comfortable and do not recline. I wouldn't suggest Allegiant for anything more than 2 hours and that was even pushing it."
Cons: "We arrived 3.5 hours early and the line was very long. They must have had a system glitch but didn't communicate to anyone in the line as to what was going on. When it did come time to board, they told everyone in the line that was going to Cincinnati that we couldn't check in until 2 hours before the departure time. Apparently there were some other flights that left before us. If they had told us to keep our place in line and to let other people through, that wouldn't have been a problem. But, they didn't. Their own website says you should check baggage at least 2 hours before your flight and no more than 4 hours before. They took it upon themselves to change the rules on people who arrive early. Then, once they no longer had anyone else to check in, they changed their rules again and start checking in people for Cincinnati about 2.5 hours ahead of time. A little communication and brain power from the staff would have gone a long way. After all that mess, the flight was delayed leaving about 15 minutes without any updates from Allegiant either."
Pros: "Love this flight from Belleville to Punta Gorda. On time and great crew."
Cons: "Nothing!!"
Pros: "Flight was cancelled due to Irma in Florida. Customer service agent was fantastic. I was able to rebook die the following week without any hassle."
Cons: "I didn't get to fly to Florida when I first chose."
Pros: "Great price. Direct route. Friendly gate staff and flight crew. On time (actually early) departure and arrival."
Cons: "Flip side of departing early is they closed boarding over 30 minutes before scheduled departure (nearly missed flight)."
Pros: "Flight went smooth"
Cons: "I checked into my flight with luggage to check in. The lady behind the counter said I could not check my luggage that the only way for it to get on the plane was to take it through the TSA checkpoint. They confiscated everything in my bag that was over 3oz which was quite a bit of stuff hence the reason why I was trying to check it in. I will not be flying Allegiant air again."
Pros: "The plane was clean"
Cons: "You have to pay to choose your seat, to have more than one carry on bag (literally of any size!!), and for any food. Nothing is complimentary. The seats don't lean back at all. No headrest adjustment for any sort of comfort. The seats are hard. We had a 30 min. Delay for some reason we were not made aware of and no apology was made. No Tv's or even a pocket in the seat-back in front of you. Basically if you can fly anything else other than this airline you are probably better off. Delta is basically the exact opposite of this airline and even American does way more. If I can help it I will never use this airline again."
Cons: "Old plane with fixed seats with very limited leg room which were not comfortable- broken window shades, scratched windows, & rattles everywhere made for a long flight. Crew was ok, I would fly again if the price was enough of a savings"
Pros: "Last week I flew to Florida on this airline. I quickly wrote a stellar review because the flight crew was sincere, nice and kind. Apparently, that is against policy and on this flight there was no hint of that nice attitude. No frills, no courtesy, just transportation."
Cons: "I flew to my "surprised" 50th bday party with family and to meet more family. The aircraft problems overheated engine, caused us to get out of the plane, move all luggages and wait foe a new plane that also had to be cooled off before reboarding. We were tired and hungry. Missed my bday with family. Very very disappointed."
Cons: "Our flight was delayed dor 10 hours."
Pros: "Seats were clean and nice"
Cons: "One crew member clearly is a disgruntled employee. It also should be against the law not to provide water without payment."
Cons: "The flight got cancelled - trip had to be completely rearranged."
Cons: "No leg room!"
Pros: "direct flight to where i wanted to go was great initial fare was very low, add-ons added up though."
Cons: "flight out was handled by Miami Air, lost the money i spent on a seat. everything costs extra, including printing a boarding pass. the app wouldn't let me check in so i had to go to the desk. i had to show the person that the app told me to go the desk then she printed the pass for free."
Pros: "Most uncomfortable plane that I've ever been on"
Cons: "Seat space"
Pros: "The crew was very accommodating, especially a flight attendant named Petra."
Cons: "We waited a long time to board. It would have been helpful if someone explained why we waiting so long."
Cons: "Row 14 has minimal leg room"
Pros: "Plane was on time."
Cons: "Even as I was checking in for the flight, as an economy traveler, I was constantly reminded of all the things I wasn’t entitled to -all boarding was based on how much you’d paid, not where you were sitting. I didn’t expect special treatment, but once you’re at the gate, boarding agents usually treat passengers equally. Not so with United."
Pros: "Honestly, don’t care for this airline. There’s always some hiccups with boarding, ride staff, mediocre cabin, etc."
Cons: "Why do they always want to check bags that are your everyday carryon items (large purse, medium backpac, etc.), but allow people to carryon their larger carry on suitcases filling up the overhead bins. Those are the people they should be making check their “carry-one.” And then be rude about it on top of that."
Cons: "There HAS to be a different snack choice than just salted pretzels, right? Not everyone is a fan of those. And although it may have been a last-minute issue, learning that there was no WiFi as we ascended 10,000’ into the air was quite disappointing. No techie around to troubleshoot that while we were boarding? Otherwise, the flight was uneventful and the crew was pleasant enough."
Pros: "Professional staff and clean seat with smooth pilot who was not constantly announcing things"
Cons: "Small seats"
Pros: "Everything went smoothly. Only a couple delays."
Cons: "The ease of travel."
Pros: "Refund was prompt"
Cons: "Flight was canceled"
Pros: "Didn’t have any food, so there should be an NA option. It was a smooth trip from start to finish with very helpful ground and in flight staffs."
Pros: "The crew from the ticket agents all the way up were great. The app for iPhone is great."
Cons: "I paid for 30 minutes of WiFi to download the United app on my iPad. I wanted to watch the movies/tv shows that were available to passengers. The WiFi was spotty and slow so I wasn’t able to load the app. Needless to say I was disappointed. I also was disappointed with the seating. I am an average size person and I felt very cramped in my seat. My shoulders and neck are killing me after a 2 hour flight. I know that I chose the economy seating but I don’t remember the seats being quite so narrow or the leg room being non existent."
Pros: "Relatively short TSA, arrived at gate just as Group 1 was boarding, hopped in my seat, and enjoyed a quick, easy flight with a surprisingly good lunch of paella, salad, and torte. Very tasty. Service was great. Nice route."
Cons: "It was a 737-300 so a bit dated of an aircraft, but it was - at least - clean."
Cons: "Long delay."
Pros: "Despite a slight delay in take off the flight landed on time; crew was friendly and efficient"
Cons: "Couldn't get a seat assignment until I arrived at the gate; boarding was slow and a little disorganized; seats are small"
Pros: "Our flight was changed a total of 6 times. We spent 9 hours waiting because their wasn't a crew. When we tried to board our seats apparently we're given away to someone else. I will never be on another united flight again"
Pros: "Competent, organized, pleasant and efficient staff, on time"
Cons: "Terrible flight!"
Cons: "The delay in my flight and that nothing was done to compensate that my entire schedule had to be redone to meet the needs of late air crafts, not enough fule and cargo doors not being able to shut."
Cons: "They had flight delay issues and WE got pushed onto a next day flight but WE had to pay for our hotel when it was their planes delayed!"
Cons: "Our plane was constantly moved around prior to boarding and it was 2 hours late."
Pros: "The flight attendants were very nice."
Cons: "The seating was a little tight but overall it was a really good flight."
Pros: "Service"
Pros: "Nothing at all"
Cons: "How they wouldn't even hand out a cup of water to anyone....."
Pros: "they switched our flight in boston to another flight which was totally inconvenient. then the connecting flight was delayed so we had a three hour layover. then they switched the terminal and flight time to an hour earlier than posted w/o our knowledge. that flight left and we were stranded in new jersey airport until 6 am the next day and had to rebook. now we will have to make another stop in san Francisco's before getting to portland oregon a day late. total joke."
Pros: "Staff was great, friendly, and accommodating"
Cons: "Upgraded to first thinking i would be more comfortable and have a decent meal...wrong...seats were so blown out that my butt and back were in pain most of the flight. Caught food posioning from the rice pilaf. I dig that united offers inflight entertainment through your phone but its annoying that i have to hold up my phone i watch something but now I'm just nitpicking."
Pros: "Nothing"
Cons: "Our plane departed on time, 6:05 AM. About 6:40 A E turned back towards Boston. There was a problem with the wing. It got repaired. We deplaned. And waited. And waited. Then we needed fuel to be removed. And we waited. And waited. Then we got back on board, got to the runway, and the RIGHT ENGINE didn't start. So they tried to repair it, couldn't (didn't want to fly on that old, broken plane anyway at this point), and we had our flight canceled. All told, I spent 10+ hours at Logan Airport. It was an absolute disaster."
Pros: "great crew!"
Pros: "The flight was bumpy but otherwise pleasant"
Cons: "There was a rude passenger that yelled at me as I was exciting the flight suggesting that I cut her off as we were getting off the plane thinking that I took her bag. It was outrageous and completely ruined the flight for me. I realize this has nothing to do with the flight but it just made me feel so crumby and attached that I felt the need to share it. Also the leg room was a joke. We barely had any room to move. I probably won't fly coach on united again due to the bad taste it left in my mouth. Unfortunate because it's hub is in chicago."
Cons: "Bereavement switched flights for me thanks"
Pros: "No complaints whatsoever."
Cons: "The crew was rude and acted as if us being there was a nusence."
Cons: "I missed my flight to San Diego from a connecting flight by a few minutes. Now I have to sit in the airport for over three hours waiting for my next flight.. not to mention it's my bday. Thanks United."
Pros: "Good crews."
Cons: "The UA439 flight from Boston to Chicago was delayed for almost 4-hours."
Pros: "Between the rude and smippy flight crew, getting kicked out of my premium seat for a flight attendant with only a promise of a refund if I saw the gate agent when I landed, and the a/c quitting mid flight to turn the plane into a flying sauna, I now remember why I hate to fly United."
Cons: "No food to rate, no entertainment to rate"
Pros: "Boarding was prompt"
Cons: "."
Cons: "Flight was delayed 3 times, I was rebooked on another flight, lost my upgraded economy plus seat and was squished in the windrow seat beside a larger man. I was traveling with my infant son which made everything a lot more stressfull! Then missed my connection in Chicago"
Cons: "Our flight home we couldn't land in Chicago due to storms and diverted to Madison. Sat on Tarmac 2 hours and some passengers from Madison allowed to end journey there. We had to wait for that approval and again had to wait for their luggage to be removed from the plane. My opinion is let them disembark but not the luggage. It was too long to be in that plane"
Cons: "They mis-tagged my bag and still haven't found it and have not been helpful or informative when I call to check the status"
Cons: "Seats are too close together. I could barely fit my knees in, and I'm not an overweight person."
Pros: "United doesn't care about customers, It was nothing to like about this flight over four hours late, the flight went to it's destination and came back, seems like every other United flight was canceled, Dora huge line about 2 to 3 hours long to get you an agent, there were no hotels available, slept in the airport"
Cons: "Flight over four hours late, had to sleep in the airport on the chairs, because there was no hotels left, United didn't offer anything, I'm really displeased with them"
Pros: "The flight attendents were attentive and did a great job."
Cons: "Customer service was rude to us about our carry on. It was fine on the way to Boston, but made to pay and check it on the way back. other customers had bags our size but we we're rudely told "you need to go pay for your bag that's it". The bag fit effortlessly in the top on the way there."
Pros: "Nothing"
Cons: "Long complicated and rude"
Cons: "Had to gate check bag both ways. Flight extremely delayed on way home causing me to miss connection; minimal communication from gate crew. A complimentary drink included a Dixie cup full of soda."
Cons: "Delays, had to stay overnight in Chicago since we arrived 6 hours late"
Cons: "I like everything from this."
Cons: "For reasons known only to them, United managed to separate the reservations of my wife and mine. Having paid for the trip with the Mileage Plus Explorer card, the first checked bag is free for each traveler. At the kiosk check-in at Logan, the machine wanted to bill us $25 to check my wife's bag. It took another 20 minutes to get this rectified."
Pros: "Crew was very nice."
Cons: "Plane aisle was a tight squeeze with carry on bag plus seats were very close together, and I'm a small person at 5'1". Otherwise flight was good."
Cons: "Two time delayed"
Pros: "went smoothly"
Cons: "lack of free peanuts"

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Boston - Chicago Flights

Departure:

Boston (BOS)United States

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Chicago - Boston

Cabin classes:

$420
$625
$297
$94

Browse origins:

$138

Compare transportation modes for Boston to Chicago

Average priceAverage duration
Flights$3512h 48m
Trains$19222h 15m