BOS - ORD
Find cheap flights from Boston to Chicago O'Hare Airport from $80
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 6/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.Round-trip
1 adult
Economy
Wed 7/5
Wed 7/12
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Travel better, cheaper and quicker. We've already found some great deals that could save you time and moneyWhen are you traveling?Good to know
Low season | February |
|---|---|
High season | June |
Cheapest flight | $80 |
Average price round-trip | $285 |
Good deal round-trip | $276 |
Good deal one-way | $153 |
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Boston to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less
or less
When to book flights from Boston to O'Hare Intl
Estimated round-trip price
Average price per month
Flight prices as travel date approaches
Top tips for finding a cheap flight from BOS to Chicago O'Hare Airport
- Looking for a cheap flight? 25% of our users found flights on this route for $153 or less one-way and $276 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 February.
- Morning departure is around 16% cheaper than an evening flight, on average*.
- You'll easily find a nonstop flight going from Boston Logan International (BOS) to Chicago O-Hare International Airport (ORD). If you have a layover, you'll probably change planes in either Philadelphia, Detroit, or Washington, D.C. On average, these are short layovers of less than 2h.
- If you drive yourself to Boston Logan International (BOS) for your trip, you'll have the option of parking in a garage or an uncovered parking lot. You can save money by parking in the economy garage which is just a few minutes from the airport. A complimentary shuttle will take you to the airport from the garage.
- Withdraw money for your trip to Chicago at one of the ATM machines at the Boston Logan International Airport (BOS). There is an ATM machine in Terminal A, Terminal B, Terminal C, and Terminal E.
- Amenities and services at the Boston Logan International Airport (BOS) include baggage trolleys, a shoe shine, hydration stations, a beauty salon where you can get a pedicure or manicure, a spa where you can relax with a massage, and several airport lounges with benefits like complimentary beverages, television, and comfortable seating.
- Passengers who are delayed or have a late flight to Chicago will benefit from its on-site hotel. There is a Hilton Chicago O'Hare Hotel across from Terminals 1, 2, and 3. Along with sleeping rooms, the hotel has a variety of amenities such as a fitness center and sports bar.
FAQs for booking Boston to Chicago O'Hare Airport flights
Top 5 airlines serving from Boston to O'Hare Intl
Scores according to KAYAK customer reviews8.1
JetBlueOverall score based on 19444 reviews
78food
79entertainment
82overall
83boarding
86crew
82comfort
Airline reviews
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."
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."
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."
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."
Cons: "clearly communicate delays. We had no idea what was happening or what our options were."
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: "Delayed boarding but made up for lost time in the air"
Cons: "Delayed boarding"
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: "Announcements were too loud in earphones (could damage ear drums) and entertainment was turned off while waiting 30 min for the gate to open."
Pros: "The crew really kept us updated on the many delays."
Cons: "There were SO many delays and they kept changing. At one point we got on and off the plane."
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: "Nothing."
Cons: "Flight was delayed 2 hours. Even though I had carry on, they checked it and this made me waste my time at baggage claim rather than gate checking. Flight attendants were miserable. Power supply didn’t work at seats."
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: "The seats were ok."
Cons: "The flight was delayed over 3 hours so I missed my connection in Chicago to Seattle. I’m now stick in Chicago overnight and have to be on a 6 am flight tomorrow. The Delta staff at LaGuaurdia was extremely rude and not helpful at all. Hate Delta......"
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: "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: "Seats seem to get smaller but overall a good experience"
Cons: "Seat room"
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."
Cons: "Baggage claim number was wrong. They almost took my bag away"
Cons: "If I actually made my connection. Delayed flight out of Boston"
Cons: "There was no entertainment at all, and pretzels are gross"
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."
Cons: "I flew on JetBlue before this flight and legroom was much better. My knees are kind of bruised after the United flight. Otherwise the flight was fine."
Pros: "Professional staff and clean seat with smooth pilot who was not constantly announcing things"
Cons: "Small seats"
Pros: "Relaxed flight- no issues with boarding. Very close gate transfer"
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: "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: "My flight was cancelled for bad weather. It was the ONLY FLIGHT going to or from Chicago cancelled. Typical United. Never flying United again."
Pros: "The courteous agent at the gate"
Cons: "Not being able to get a flight over 20 hours later!"
Pros: "I got to where I wanted to go"
Cons: "I reached out to your customer support already about this, but haven't heard back. The departure time (for both legs of my trip) that was confirmed with my purchase from Kayak was incorrect and caused a major inconvenience. I'd very much like to receive a response. My email addres"
Cons: "The plane was delayed due to “maintenance” but no explanation was given as to why."
Pros: "Crew was very nice"
Cons: "Better off paying more upfront with any other airline. As tickets will end up being same by the time you finish paying for luggage and your seat. Not worth the hassle and discomfort"
Pros: "Smooth flight and pilot a spoke to us a couple times"
Cons: "Stewardess over intercom had poor diction."
Pros: "Good boarding process"
Cons: "A crew member had a very loud, extremely personal conversation for the entire duration of an early morning flight. She made eye contact so I knew she knew what she was doing"
Pros: "The crew was nice and they were apologetic. I know it wasn't their fault. They gave status updates every 15 minutes but in the end they were generally 'wrong'. Some people were angry about this but it wasn't their fault. How could it be? They were just repeating what they were told. It's not their fault that their organizers told them incorrect stuff. I sympathized with them more than I usually would because some passengers were such jerks to them. I appreciate that they were keeping us in the loop. We basically knew as much as they knew. It made me feel like we were all in this bad situation together, which we were. They wanted to get home, too. That was the right way to handle this. The actual flight was uneventful. Plane was clean. Seats were about as comfortable as you would expect for the price."
Cons: "Where to begin. It was delayed 1.5 hours, then we boarded, waited maybe 30 minutes, then we UNBOARDED because they needed a new plane, then it was delayed AGAIN. When we finally landed in Chicago we were about 5 hours behind schedule. I feel bad for the crew because they were left dealing with angry passengers, I know it wasn't their fault. Just poor corporate planning. In addition I did have a truly mind boggling experience with an employee. We were lined up for our first boarding, in a huge line, having waited for 1.5 hours, and suddenly a woman with multiple bags cut in line. I said "Excuse me ma'am but there IS a line" and she smiled and said "Oh, sorry, I'm an employee". I apologized and she cut everyone and boarded. That's when I realized that she was NOT WORKING THE FLIGHT. She was just using her privilege to cut in line. She cut in front and saved maybe 5 minutes. I mean, why bother. Why bother pissing off paying customers to save 5 minutes. People around me were so angry. Then she got on the flight and held everything up because she needed to load her 4 pieces of luggage into the overhead bin, taking up an entire bin. Flight crew actually moved people's bags to accommodate her. And one of her bags was a full sized suitcase that would never have been allowed if she wasn't an employee. Simply ridiculous, the only thing saving her was that there were open seats. She was not taking a seat from a paying customer. I would say that I wouldn't fly Frontier again but honestly all of the companies suck so I don't know who to pick. Every airline has some story or another of crappy customer service. I wish the barrier for entry wasn't so high so that competitors could swoop in....as much as I dislike the Elon Musk's of the world it would be great if some billionaire swooped in with their money and made an airline that actually worked."
Pros: "on time and efficient"
Cons: "gave me seat in row 30 when other seats were empty"
Pros: "expeditious boarding, low fare"
Cons: "bad seats they do not recline of a 3-plus hour flight, no snacks or drinks without charges,"
Pros: "Friendly crew Fairly clean air craft"
Cons: "Seats don't boot recline There is not even one complementary drink during duration of a flight"
Pros: "Lower cost, but sacrifice comfort and amenities, flight attendants fine"
Cons: "Sat in row 26, nothing except bare bones service"
Book cheap flights from Boston to Chicago O'Hare Airport
Recent round-trip flight deals
8/15Tue
1 stopSpirit Airlines
6h 56mBOS-ORD
8/22Tue
1 stopSpirit Airlines
9h 08mORD-BOS
$163
7/18Tue
1 stopSpirit Airlines
11h 13mBOS-ORD
7/19Wed
1 stopSpirit Airlines
8h 15mORD-BOS
$165
7/5Wed
nonstopMultiple Airlines
3h 06mBOS-ORD
7/12Wed
1 stopMultiple Airlines
8h 15mORD-BOS
$171
6/20Tue
1 stopSpirit Airlines
6h 17mBOS-ORD
6/22Thu
1 stopSpirit Airlines
9h 01mORD-BOS
$173
9/6Wed
nonstopJetBlue
2h 59mBOS-ORD
9/13Wed
nonstopJetBlue
2h 24mORD-BOS
$178
6/20Tue
1 stopSpirit Airlines
6h 17mBOS-ORD
6/21Wed
1 stopSpirit Airlines
16h 59mORD-BOS
$181
7/13Thu
1 stopSpirit Airlines
11h 38mBOS-ORD
7/19Wed
1 stopSpirit Airlines
8h 15mORD-BOS
$183
7/4Tue
nonstopMultiple Airlines
3h 06mBOS-ORD
7/11Tue
1 stopMultiple Airlines
10h 16mORD-BOS
$187
9/6Wed
nonstopJetBlue
2h 59mBOS-ORD
9/13Wed
1 stopJetBlue
5h 18mORD-BOS
$188
8/23Wed
nonstopAmerican Airlines
2h 54mBOS-ORD
8/28Mon
1 stopAmerican Airlines
4h 56mORD-BOS
$191
9/28Thu
nonstopAmerican Airlines
2h 57mBOS-ORD
10/11Wed
1 stopAmerican Airlines
4h 44mORD-BOS
$192
8/31Thu
1 stopAmerican Airlines
5h 42mBOS-ORD
9/3Sun
nonstopAmerican Airlines
2h 21mORD-BOS
$193
9/28Thu
nonstopAmerican Airlines
2h 57mBOS-ORD
10/2Mon
1 stopAmerican Airlines
4h 48mORD-BOS
$194
6/21Wed
2 stopsSpirit Airlines
23h 27mBOS-ORD
6/23Fri
1 stopSpirit Airlines
16h 59mORD-BOS
$196
8/25Fri
1 stopJetBlue
4h 29mBOS-ORD
8/28Mon
1 stopJetBlue
7h 38mORD-BOS
$197
7/19Wed
nonstopMultiple Airlines
3h 06mBOS-ORD
7/25Tue
1 stopMultiple Airlines
10h 16mORD-BOS
$202
8/21Mon
nonstopJetBlue
3h 06mBOS-ORD
8/26Sat
1 stopJetBlue
7h 38mORD-BOS
$203
8/30Wed
1 stopAmerican Airlines
5h 21mBOS-ORD
9/2Sat
1 stopAmerican Airlines
5h 43mORD-BOS
$204
8/30Wed
nonstopDelta
2h 48mBOS-ORD
9/2Sat
nonstopDelta
2h 31mORD-BOS
$208
8/17Thu
1 stopJetBlue
4h 29mBOS-ORD
8/20Sun
1 stopJetBlue
7h 38mORD-BOS
$212
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6/20Tue
1 stopMultiple Airlines
18h 23mBOS-ORD
$80
7/26Wed
1 stopSpirit Airlines
8h 39mBOS-ORD
$82
8/16Wed
1 stopSpirit Airlines
11h 21mBOS-ORD
$84
6/14Wed
nonstopUnited Airlines
2h 49mBOS-ORD
$89
7/25Tue
nonstopDelta
2h 48mBOS-ORD
$90
6/28Wed
1 stopSpirit Airlines
6h 14mBOS-ORD
$92
8/15Tue
1 stopSpirit Airlines
9h 43mBOS-ORD
$95
8/19Sat
1 stopSpirit Airlines
6h 42mBOS-ORD
$96
8/2Wed
1 stopSpirit Airlines
11h 38mBOS-ORD
$97
7/4Tue
1 stopUnited Airlines
6h 58mBOS-ORD
$99
9/7Thu
1 stopAmerican Airlines
5h 20mBOS-ORD
$102
6/14Wed
1 stopAmerican Airlines
5h 06mBOS-ORD
$109
8/17Thu
1 stopJetBlue
4h 29mBOS-ORD
$114
7/7Fri
nonstopUnited Airlines
2h 47mBOS-ORD
$119
8/14Mon
1 stopMultiple Airlines
17h 19mBOS-ORD
$121
7/25Tue
1 stopMultiple Airlines
18h 22mBOS-ORD
$123
8/7Mon
1 stopMultiple Airlines
16h 59mBOS-ORD
$124
7/8Sat
1 stopAmerican Airlines
5h 11mBOS-ORD
$127
6/11Sun
1 stopAmerican Airlines
4h 50mBOS-ORD
$129
7/3Mon
2 stopsFrontier
19h 46mBOS-ORD
$135
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Boston - Chicago O'Hare Airport Flights
Departure:
Boston (BOS)United States
Destination:
Chicago O'Hare Airport (ORD)United States
Return flight deals:
Chicago O'Hare Airport - Boston
Cabin classes:
$614
$682
$537
$128