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BOS - CHI

$23 Find cheap flights from Boston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Chicago departing on 9/28. 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
Sun 8/25
Sun 9/1

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
In the last 7 days travelers have searched 50,552,696 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Chicago 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
11:35 am - 1:27 pmBOS-ORD
2h 52mnonstop
2:17 pm - 5:42 pmORD-BOS
2h 25mnonstop
$40Spirit Airlines
Find Deal
Sat, Oct 5 - Tue, Oct 8
11:35 am - 1:27 pmBOS-ORD
2h 52mnonstop
2:17 pm - 5:42 pmORD-BOS
2h 25mnonstop
$47Spirit Airlines
Find Deal
Sat, Sep 7 - Sat, Sep 14
8:00 am - 9:53 amBOS-ORD
2h 53mnonstop
2:17 pm - 5:42 pmORD-BOS
2h 25mnonstop
$48Spirit Airlines
Find Deal
Tue, Aug 27 - Tue, Sep 10
11:08 am - 3:51 pmBOS-MDW
5h 43m1 stop
4:46 pm - 12:27 amMDW-BOS
6h 41m1 stop
$103Frontier
Find Deal
Wed, Aug 28 - Wed, Sep 4
6:00 am - 10:19 amBOS-MDW
5h 19m1 stop
2:30 pm - 12:30 amMDW-BOS
9h 00m1 stop
$104Frontier
Find Deal
Tue, Sep 10 - Tue, Sep 17
5:10 am - 8:40 amBOS-ORD
4h 30m1 stop
8:20 pm - 11:52 pmORD-BOS
2h 32mnonstop
$147JetBlue
Find Deal
Thu, Sep 5 - Mon, Sep 9
6:30 am - 8:20 amBOS-ORD
2h 50mnonstop
8:33 pm - 11:59 pmORD-BOS
2h 26mnonstop
$157JetBlue
Find Deal
Sat, Aug 24 - Fri, Aug 30
6:00 am - 7:48 amBOS-ORD
2h 48mnonstop
6:34 pm - 10:06 pmORD-BOS
2h 32mnonstop
$167United Airlines
Find Deal
Fri, Sep 20 - Fri, Sep 20
7:30 am - 9:30 amBOS-ORD
3h 00mnonstop
1:59 pm - 5:41 pmORD-BOS
2h 42mnonstop
$184Delta
Find Deal
Thu, Aug 8 - Mon, Aug 19
11:05 am - 12:59 pmBOS-ORD
2h 54mnonstop
6:56 pm - 10:32 pmORD-BOS
2h 36mnonstop
$187Delta
Find Deal
Fri, Aug 16 - Fri, Aug 16

Flights from Boston to Chicago - Travel Insights & Trends

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

What is the cheapest Boston to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Boston to Chicago.
Our data shows that the cheapest route for a one-way flight from Boston to Chicago cost $58 and was between Boston and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from Boston to Chicago Midway Airport. The average price for a return flight for this route is $74.

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

The average price of all flights from Boston to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Boston to Chicago, you should consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Chicago, 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 Boston to Chicago is January, where tickets cost $186 on average. On the other hand, the most expensive months are April and May, where the average cost of tickets is $300 and $293 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Chicago, 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 Boston to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 146 days before departure.

Which airlines provide the cheapest flights from Boston to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Boston to Chicago were found on Spirit Airlines ($40) and Frontier ($103). Spirit Airlines proposed the cheapest one-way flight at $23.

Which airlines fly most frequently between Boston and Chicago?

Boston and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (55 flights per week), United Airlines (52 flights per week), and Southwest (39 flights per week).

Which airlines fly non-stop between Boston and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Boston to Chicago.
There are 6 airlines that fly nonstop from Boston to Chicago. They are: American Airlines, Delta, JetBlue, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $39 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 Boston and Chicago per day?

Each day, there are between 23 and 29 nonstop flights that take off from Boston and land in Chicago, with an average flight time of 2h 49m. The most common departure time is 5:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 193 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

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

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 Boston to Chicago take?

The duration of a nonstop flight to Chicago from Boston is typically 2h 40m. The journey crosses a distance of 850 miles.

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

Early birds can take the earliest flight from Boston at 5:15 am and will be landing in Chicago at 7:10 am.

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

If you prefer to fly at night, the latest flight from Boston to Chicago jets off at 10:06 pm and lands at 11:59 pm.

Good to know

Low season

January

High season

July

Cheapest flight

$23
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Boston to Chicago O'Hare Airport

When to book flights from Boston to Chicago

Are your dates flexible? Find out the best times to travel from Boston to Chicago 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 Boston to Chicago

  • What are the most sustainable airlines with Boston to Chicago flights?

    Porter Airlines, United Airlines and American Airlines offer some of the most environmental-friendly flights to Chicago from Boston. Their flights emit about 48%, 46% and 42% less carbon respectively than their competitors. Those looking to fly more sustainably from Boston to Chicago should prioritize nonstop flights, embrace the use of recycled plastics and pack light for the trip.

  • What are the parking options at Boston Logan International Airport (BOS)?

    If you’ll be driving to the airport, you’ll be happy to know that Boston Logan International Airport (BOS) offers convenient onsite parking options. Parking is available in Central Parking Garage, Economy Garage, and the Terminal B Garage. All the parking garages are easily accessible from the terminals by the moving sidewalks and walkways. Additionally, the airport partners with other agencies to offer multiple secure offsite parking options.

  • What accessible services are offered at Boston Logan International Airport (BOS)?

    Boston Logan International Airport (BOS) provides Braille and Emergency Call keys in elevators. All restrooms within the airport are accessible, and it also provides restrooms for the companions. To enhance transit for passengers with reduced mobility, BOS provides Massport Shuttles. These buses are free, are equipped with wheelchair lifts and use visual and audio assistance systems to announce the bus stops. All airlines flying through BOS also run wheelchair assistance services.

  • Are there nursing rooms at Chicago O’Hare International Airport (ORD)?

    Yes, Chicago O’Hare International Airport (ORD) provides Mother's Rooms in every terminal. The rooms offer a space for traveling mothers to breastfeed or pump and are equipped with a sink, comfortable seats, power outlets and diaper changing tables. The rooms are available near Gate B10 on Concourse B in Terminal 1. In Terminal 2, they are by Gates E5 and F9. Others are also near Gate L6 in Terminal 3 and also at Gate M8​, Gate M20​, Gate M32 and Gate M37 in Terminal 5. There are also others at Multi-Modal Facility on Level 1, North and South Side.

  • If I want to use mass transit to get to Boston Logan International Airport (BOS), what is my best choice?

    The Blue Line Subway is an excellent choice for quick and reliable transportation to the airport. Save the headaches of traffic by taking the MBTA Blue Line to the station at the airport and then simply board one of the free shuttle buses to all of the airport terminal buildings.

  • Are there pet relief areas at Boston Logan International Airport (BOS)?

    The pet relief areas at Boston Logan International Airport (BOS) are located on the arrivals level of every terminal building. In addition, there is a pet relief area located in Terminal E near gate E7. Keep in mind that this is the only pet relief area that is past security.

  • If I am being picked up at Chicago O'Hare International Airport (ORD), where is the best place to meet my ride?

    For most requests, you'll meet your rideshare driver on the Departures level of Terminal 2. As a reminder, there is no parking at the terminal building at any time. It is advisable to use the cell phone lot that is provided at the airport to wait for arriving passengers rather than just circling the airport.

  • Where can I rent a car at Chicago O'Hare International Airport (ORD)?

    The airport offers a complimentary shuttle to the airport's Multi-Modal Facility, where all on-site car rental companies are located. Travelers can find the shuttle by exiting the Lower Level Baggage Claim and boarding the shuttle bus at the curb front. Each terminal has a designated pickup area outside the building.

  • What is the cheapest flight from Boston to Chicago?

    In the last 3 days, the lowest price for a flight from Boston to Chicago was $23 for a one-way ticket and $40 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    American Airlines, JetBlue, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Boston to Chicago flight route.

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

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

  • Which airline alliances offer flights from Boston to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and JetBlue. With an average price for the route of $258 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 $226 and an overall rating of 7.6.

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

    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 Boston to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston 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 Boston to Chicago?

    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 Chicago with an airline and back to Boston with another airline.

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

    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 Chicago from Boston 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 Boston to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $108 or less one-way and $184 or less round-trip.
  • 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 (LGA).
  • 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 modes of transportation.
  • Passengers flying to Chicago O’Hare International Airport (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.
  • If you need cash before flying out from Boston Logan International Airport (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.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can let off steam 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.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal Sea Foods. 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 (BOS), 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 Classique Hair Salon? Located in Terminal C near Gare C-25 at Boston Logan International Airport, Classique Hair Salon 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.
See more tips

Prefer to fly non-stop from Boston to Chicago?

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

Nonstop departures

Boston Logan Intl to Chicago

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, +21 more

ANA, Air New Zealand, +22 more

Thursday

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

ANA, Air New Zealand, +23 more

Friday

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

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +22 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights

Nonstop returns

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
See more direct flights

Top 5 airlines serving from Boston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. 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 Boston to Chicago? 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 9630 reviews
8.2Boarding
8.0Entertainment
7.4Food
8.6Crew
7.9Comfort
Airline reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

6.0 GoodKathy, Jul 2024ANC - SLC
Read more about Delta reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

Flights were terribly delayed. I was at At,anta Airport for over 4 hours waiting for my connection.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

I know it was not in Deltas fault. But numerous delays and cancelations. I requested a hotel voucher and was told they weren't available. The lady on my hotel shuttle did receive one from American. Why the difference?

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Overall fine but both ways for this trip was delayed.

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

Every Single leg of our trip was delayed signifigantly... including a new flight we had to take because we missed our connection flight due to delays.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

It was freezing in there. When I asked about it, the response is “we would have to tell them” and then she just walked away and continued to serve beverages. Everyone was cold and they didn’t care at all.

I did not enjoy continuously being lied to about the amount of time we would circle Chicago before deciding to redirect to Milwaukee. Then the amount of time we would sit on the ground in Milwaukee waiting for gas, or to take off again. Or the amount of time it would then take to get to Chicago again, or sit on the runway waiting for a gate. The whole time continuously hopefully we would make our connecting flight that kept getting delayed as well. Only to scramble and miss it. Enough with the BS. Tell me the truth. "Sorry, things are backed up and your probably not going to make your flight. You should rebook on the next flight now rather than wait." You'll never hear those words from an airline. Speaking of which. If the flight has been redirected and/or is seriously delayed, how about making the WiFi free for everyone so they get to rebooking and reserving hotel rooms while still in the air. You've inconvenienced me already and now you want me to pay $20 for Internet so I can try to make other plans. Absolutely disgusting!

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

I like the speed of boarding and deplaning and the fact that everything was on time. The crew (attendants) were probably quite new and did not begin the in cabin service until 30 min before landing even though there was little to no air turbulence for the last 1.5 hours of the flight. It made for a mad scramble at the end to get trash collected and carts stowed before touch down.

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Everything went on schedule so I have not much to say. I was a bit disappoint with the breakfast choice - I did not have a choice as there was only one option left by the time the trolly came to my end and I could not enjoy it.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

The worse experience ever from flight delays customer service and professionalism.

Terrible they delayed our flight then when we got on they had to fix the plane then finally we left hours later and when we got there since they had screwed up everything else we had to wait for a walkway so we had to sit on the plane and they turned off the AC and it was fuckin hot

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Book cheap flights from Boston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK in the last 72 hours.
9/28Sat
nonstopSpirit Airlines
2h 52mBOS-ORD
$23
9/18Wed
nonstopSpirit Airlines
2h 52mBOS-ORD
$24
9/2Mon
1 stopJetBlue
5h 11mBOS-ORD
$68
10/15Tue
nonstopJetBlue
2h 53mBOS-ORD
$69
8/1Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$91
8/2Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
$94
8/2Fri
nonstopUnited Airlines
2h 50mBOS-ORD
$111
8/27Tue
1 stopDelta
9h 17mBOS-MDW
$122
7/31Wed
1 stopDelta
4h 18mBOS-MDW
$158
9/5Thu
nonstopUnited Airlines
2h 43mBOS-ORD
$190

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Last minute flights from Boston to Chicago

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 Boston to Chicago that are departing in the next 10 days.
7/30Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
8/31Sat
nonstopSpirit Airlines
2h 28mORD-BOS
$142
7/30Tue
multi-stop
5h 44mBOS-ORD
8/6Tue
nonstop
2h 26mORD-BOS
$143
7/30Tue
multi-stop
5h 44mBOS-ORD
8/7Wed
nonstop
2h 28mORD-BOS
$148
7/30Tue
nonstopDelta
3h 01mBOS-ORD
8/6Tue
nonstopDelta
2h 42mORD-BOS
$254
7/30Tue
multi-stopDelta
4h 51mBOS-ORD
8/7Wed
nonstopDelta
2h 26mORD-BOS
$264
7/26Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
7/31Wed
nonstopAmerican Airlines
2h 27mORD-BOS
$279
7/26Fri
nonstopJetBlue
2h 54mBOS-ORD
7/30Tue
nonstopJetBlue
2h 26mORD-BOS
$352
7/26Fri
nonstopAmerican Airlines
2h 59mBOS-ORD
7/28Sun
nonstopAmerican Airlines
2h 27mORD-BOS
$353
7/28Sun
nonstopJetBlue
2h 54mBOS-ORD
7/29Mon
multi-stopJetBlue
4h 40mORD-BOS
$361
7/26Fri
nonstopUnited Airlines
2h 45mBOS-ORD
7/27Sat
nonstopUnited Airlines
2h 22mORD-BOS
$377

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Boston - Chicago Flights

Departure:

Boston (BOS)United States

Return flight deals:

Chicago - Boston

Cabin classes:

$373
$481
$364
$74

Compare transportation modes for Boston to Chicago

Average priceAverage duration
Flights$8342h 48m
Trains$24822h 17m
Buses$23031h 48m