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CHI - BOS

Find cheap flights from Chicago to Boston from $31

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Boston departing on 6/6. 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.
1 adult
0 bags
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Boston (CHI-BOS)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:08 pm - 9:43 amMDW-BOS
11h 35m1 stop
11:42 am - 6:54 amBOS-MDW
20h 12m1 stop
$99Frontier
Find Deal
Sat, May 18 - Sat, Jun 1
7:49 am - 8:40 amMDW-BOS
23h 51m1 stop
11:42 am - 6:54 amBOS-MDW
20h 12m1 stop
$110Frontier
Find Deal
Wed, May 29 - Sat, Jun 1
7:15 pm - 10:41 pmORD-BOS
2h 26mnonstop
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
$163JetBlue
Find Deal
Fri, May 31 - Mon, Jun 3
7:15 pm - 10:41 pmORD-BOS
2h 26mnonstop
4:25 pm - 6:20 pmBOS-ORD
2h 55mnonstop
$177JetBlue
Find Deal
Sat, Jun 1 - Wed, Jun 5
6:27 pm - 1:01 amORD-BOS
5h 34m1 stop
5:25 am - 7:21 amBOS-ORD
2h 56mnonstop
$196American Airlines
Find Deal
Sat, May 25 - Wed, May 29
7:46 am - 11:17 amORD-BOS
2h 31mnonstop
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$207United Airlines
Find Deal
Sun, May 26 - Tue, May 28
8:02 am - 11:34 amORD-BOS
2h 32mnonstop
5:05 pm - 7:03 pmBOS-ORD
2h 58mnonstop
$208Delta
Find Deal
Sat, Jun 1 - Sat, Jun 8
8:36 pm - 12:01 amORD-BOS
2h 25mnonstop
7:30 pm - 9:26 pmBOS-ORD
2h 56mnonstop
$212American Airlines
Find Deal
Sat, Jun 29 - Tue, Jul 2
9:45 pm - 1:20 amORD-BOS
2h 35mnonstop
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$218United Airlines
Find Deal
Fri, May 24 - Mon, May 27
8:10 pm - 11:46 pmORD-BOS
2h 36mnonstop
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
$267Delta
Find Deal
Mon, May 13 - Thu, May 16

Flights from Chicago to Boston - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Boston to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Boston flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Boston.
Our data shows that the cheapest route for a one-way flight from Chicago to Boston cost $83 and was between Chicago O'Hare Intl Airport and Boston. On average, the best prices are found if you fly from Chicago Midway Airport to Boston. The average price for a return flight for this route is $124.

What’s the cheapest day of the week to fly from Chicago to Boston?

The average price of all flights from Chicago to Boston clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Boston on a Tuesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

What is the cheapest month to fly from Chicago to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Boston is January, where tickets cost $201 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $328 and $315 respectively.

How far in advance should I book a flight from Chicago to Boston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 84 days before departure.

Which airlines provide the cheapest flights from Chicago to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Boston from Chicago were found on Spirit Airlines ($31) and Frontier ($47), and the lowest round-trip tickets were found on Frontier ($99) and JetBlue ($163).

Which airlines fly most frequently between Chicago and Boston?

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (11 flights per day), American Airlines (10 flights per day), and Southwest (8 flights per day).

Which airlines fly non-stop between Chicago and Boston?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Boston.
There are 6 airlines that fly nonstop from Chicago to Boston. They are: American Airlines, Delta, JetBlue, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with JetBlue at $69 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between Chicago and Boston per day?

Each day, there are between 27 and 43 nonstop flights that take off from Chicago and land in Boston, with an average flight time of 2h 24m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 269 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago and Boston?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Boston take?

The duration of a nonstop flight to Boston from Chicago is typically 2h 17m. The journey crosses a distance of 850 miles.

What’s the earliest departure time from Chicago to Boston?

Early birds can take the earliest flight from Chicago at 6:00 am and will be landing in Boston at 9:15 am.

What’s the latest departure time from Chicago to Boston?

If you prefer to fly at night, the latest flight from Chicago to Boston jets off at 9:45 pm and lands at 1:06 am.

Good to know

Low season

January

High season

October

Cheapest flight

$31
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago O'Hare Airport to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Boston

  • How can I get to the Freedom Trail from Boston Logan International Airport (BOS)?

    The distance between the Freedom Trail and Boston Logan International Airport (BOS) is around 3.7 miles, and various transportation options run between the two points. Line 88 bus and the subway provide the best opportunity to travel between the two points, taking about 26min to cover the distance. However, a taxi is a quicker option, taking about 6min to get there.

  • Where are spas located at Boston Logan International Airport (BOS)?

    Travelers arriving in BOS from Chicago while weary can seek some therapy in one of the spas on this property. XpresSpa at Terminal B provides ideal services to help you relax and self-indulge. They include manicures, pedicures, facials, and deep-tissue massages.

  • Where can I withdraw money at Boston Logan International Airport (BOS)?

    If your wallet is depleted and you want to recharge it, you’ll find several ATMs at BOS run by numerous banks and credit unions. These ATMs are located throughout the airport terminals, pre-and post-security. For instance, Bank of America has its ATMs at the Arrivals Level, East End by Taxi Stand, Pre-Security.

  • What family-friendly amenities are at Boston Logan International Airport (BOS)?

    BOS caters to the needs of moms and the littlest family members through the provision of Mamava suites where lactating mothers can pump and breastfeed in privacy. You can locate one of them in Terminal E post-security in the Women's Restroom lobby.

  • Does Logan International Airport have pet relief areas?

    If you are traveling with a pet or service animal, make sure to stop by one of the pet relief areas in Logan International Airport after your flight has landed. There is a designated area conveniently located outside of the Arrivals doors for every terminal, and complimentary waste bags are provided for pet owners.

  • What are good hotels near Logan International Airport?

    The Hilton Boston Logan Airport is a chic, 4-star hotel that is directly connected to Logan International Airport via a skybridge and is less than a 7-minute drive from the Boston Common Park. The Hyatt Regency Boston Harbor is a standard option that is only a mile from the airport and a 5-minute drive from the famous Faneuil Hall.

  • What dining options are there in Chicago Midway International Airport?

    The Go Go White Sox Bar and Grill is located in the Central Market of Chicago Midway International Airport and serves classic American meals, while the Midway Pour House is in Concourse A and is known for having a variety of craft beers. Dunkin’ Donuts and Cafe Espresso are good options for travelers with little time that would like to purchase some to-go items.

  • Does Logan International Airport have a prayer room?

    Logan International Airport has the Our Lady of the Airways Chapel that is located in Terminal C of the Arrivals level. It is open during standard business hours and is available to all travelers, no matter what their spiritual affiliation is.

  • What is the cheapest flight from Chicago to Boston?

    In the last 3 days, the lowest price for a flight from Chicago to Boston was $31 for a one-way ticket and $99 for a round-trip.

  • Do I need a passport to fly between Chicago and Boston?

    A passport is not required to fly from Chicago to Boston.

  • Which airports will I be using when flying from Chicago to Boston?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Boston?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, Delta, JetBlue, Finnair, British Airways, and Iberia.

  • Which aircraft models fly most regularly from Chicago to Boston?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Boston flight route.

  • Which airline alliances offer flights from Chicago to Boston?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Boston, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Boston?

    There are nonstop flights from Chicago to Boston on a daily basis.

  • Which is the best airline for flights from Chicago to Boston, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Delta and JetBlue. With an average price for the route of $263 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $228 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Chicago to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $133 or less one-way and $223 or less round-trip.
  • Travelers flying American Airlines from Chicago to Boston should remember that the airline’s hub is at Boston Logan International Airport (BOS). You’ll arrive through Terminal B, and the airline’s Admirals Club is located at the same terminal. Members and holders and registered cards enjoy unrestricted access to this amenity. However, Economy Class travelers can access it at a reduced cost.
  • If you’re departing to BOS via Chicago Midway International Airport (MDW), you’ll find a road system between the terminal and the secure area. Inter-terminal movement between the two buildings is through a pedestrian bridge. However, every traveler must be cleared at the security checkpoint in the terminal building on the way out to the concourse.
  • Suppose you’re flying aboard Delta Airlines from Chicago O’Hare International Airport (ORD) to Boston Logan International Airport (BOS). In that case, you’ll be glad to note that the carrier allows pets such as cats and dogs in the cabin. Nevertheless, your four-legged friends must bear certified vaccination certificates and relevant health licenses. Still, it would help if you confined them in their cages to prevent them from disturbing other passengers.
  • Chicago Midway International Airport (MDW) sits about 10.7 miles from Downtown Chicago, and several public transportation options travel between the two destinations. The most convenient commute from downtown Chicago to MDW is via the Orange Line train. The train regularly plies between the two points, covering the distance in approximately 20-25min.
  • Before your trip from Chicago to BOS, you might wish to have a private session with the Almighty. Those departing through ORD will be glad to know that this prayer suite is tucked away from the noisy terminals. The airport’s chapel lies on the Mezzanine level of Terminal 2, atop the Delta Air Lines ticket desk.
  • If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
  • Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
  • For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
  • To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
  • Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
See more tips

Prefer to fly non-stop from Chicago to Boston?

Find which airlines fly direct from Chicago to Logan Intl, which days they fly and book direct flights.

Nonstop departures

Chicago to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights

Nonstop returns

Boston Logan Intl to Chicago

Monday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10818 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

Delayed abs delayed Gate crew giving poor info - we are definitely leaving at —- Ultimately to cancel flight after 4+ hours of delays Just cancel it earlier

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

This plane is my favorite despite the very limited overhead space. Seats are comfortable!

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

Service was awesome 👍🙏 thank you Spirit Airlines...love the Big Seat...😎

Crew was very engaging and welcoming. Seat very uncomfortable and inadequate leg room made the trip a long 3 hours.

Plane two hours late. Missed flight to Boston. Spirit should have already reticketed us at the last jet blue flight. But no. No help, only confusion. Reticketing line a mile long. Agent couldn’t care less whether I lived or died. Offered flight two days later - unacceptable. Now going - hopefully - via Orlando to Boston with a 7 hour layover. Locator GJLSJG BTW, am a travel counselor at a large corporate agency.

The flight was delayed. The boarding process disorganized. Poor communication regarding the delays. We were sitting on the runway in Boston for over 1-hr. Again very poor communication regarding the status. Bags didn’t arrive after almost 2-hr wait. I gave up and went home without my bag and had to return to the airport to pick it up the next day. Very exhausting experience!

Book cheap flights from Chicago to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
6/6Thu
nonstopSpirit Airlines
2h 28mORD-BOS
$31
6/18Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$32
5/29Wed
nonstopJetBlue
2h 26mORD-BOS
$69
7/5Fri
nonstopAmerican Airlines
2h 27mORD-BOS
$95
5/14Tue
nonstopJetBlue
2h 26mORD-BOS
$99
7/5Fri
nonstopDelta
2h 34mORD-BOS
$104
5/12Sun
1 stopUnited Airlines
5h 41mORD-BOS
$118
7/3Wed
1 stopAmerican Airlines
4h 05mORD-BOS
$129
5/13Mon
nonstopDelta
2h 36mORD-BOS
$134
5/16Thu
nonstopUnited Airlines
2h 21mORD-BOS
$160

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Last minute flights from Chicago to Boston

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Boston that are departing in the next 10 days.
5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/18Sat
multi-stopFrontier
22h 05mBOS-MDW
$97
5/11Sat
multi-stopFrontier
10h 51mMDW-BOS
5/18Sat
multi-stopFrontier
20h 25mBOS-MDW
$102
5/11Sat
multi-stopSpirit Airlines
13h 06mORD-BOS
5/14Tue
multi-stopSpirit Airlines
24h 39mBOS-ORD
$140
5/11Sat
nonstopDelta
2h 31mORD-BOS
5/14Tue
nonstopDelta
3h 02mBOS-ORD
$197
5/11Sat
nonstopAmerican Airlines
2h 17mORD-BOS
5/16Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$218
5/11Sat
nonstopAmerican Airlines
2h 26mORD-BOS
5/14Tue
multi-stopAmerican Airlines
5h 22mBOS-ORD
$226
5/11Sat
nonstopDelta
2h 31mORD-BOS
5/14Tue
multi-stopDelta
7h 27mBOS-ORD
$257
5/7Tue
nonstopUnited Airlines
2h 23mORD-BOS
6/9Sun
nonstopUnited Airlines
2h 50mBOS-ORD
$279
5/8Wed
nonstopJetBlue
2h 29mORD-BOS
5/11Sat
nonstopJetBlue
2h 55mBOS-ORD
$369
5/7Tue
nonstopJetBlue
2h 26mORD-BOS
5/11Sat
nonstopJetBlue
2h 54mBOS-ORD
$373

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Flights to Boston

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Chicago

Cabin classes:

$396
$615
$394
$124

Compare transportation modes for Chicago to Boston

Average priceAverage duration
Flights$4452h 26m
Trains$29521h 56m
Buses$23727h 18m