BOS - ORD

₹ 3,941 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 O'Hare Intl departing on 18/8. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, as well as popular online travel agencies
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Cheap Flights from Boston to Chicago (BOS-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return 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 for you by selecting your travel dates on KAYAK.

Recent return flight deals from Boston to O'Hare Intl

Thu, 21 Aug - Mon, 25 Aug
United Airlines Logo
09:43 - 11:33BOS-ORD
2h 50mdirect
United Airlines Logo
06:30 - 09:56ORD-BOS
2h 26mdirect
₹ 7,797United Airlines
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Sat, 30 Aug - Tue, 2 Sep
American Airlines Logo
16:00 - 17:55BOS-ORD
2h 55mdirect
American Airlines Logo
07:00 - 10:24ORD-BOS
2h 24mdirect
₹ 7,882American Airlines
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Tue, 12 Aug - Wed, 13 Aug
United Airlines Logo
19:04 - 23:41BOS-ORD
5h 37m1 stop
United Airlines Logo
07:30 - 10:57ORD-BOS
2h 27mdirect
₹ 8,311United Airlines
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Tue, 12 Aug - Fri, 22 Aug
JetBlue Logo
06:00 - 07:55BOS-ORD
2h 55mdirect
JetBlue Logo
08:40 - 12:04ORD-BOS
2h 24mdirect
₹ 8,397JetBlue
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Sat, 30 Aug - Wed, 3 Sep
Southwest Logo
08:00 - 16:25BOS-ORD
9h 25m1 stop
Southwest Logo
15:10 - 22:30ORD-BOS
6h 20m1 stop
₹ 8,482Southwest
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Sat, 6 Sep - Wed, 10 Sep
Southwest Logo
06:15 - 13:05BOS-ORD
7h 50m1 stop
Southwest Logo
15:10 - 22:30ORD-BOS
6h 20m1 stop
₹ 8,825Southwest
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Wed, 3 Sep - Sat, 6 Sep
Southwest Logo
07:05 - 14:10BOS-ORD
8h 05m1 stop
Southwest Logo
13:30 - 22:15ORD-BOS
7h 45m1 stop
₹ 8,911Southwest
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Sun, 24 Aug - Sun, 31 Aug
JetBlue Logo
06:00 - 07:55BOS-ORD
2h 55mdirect
JetBlue Logo
08:40 - 12:04ORD-BOS
2h 24mdirect
₹ 8,996JetBlue
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Fri, 5 Sep - Sun, 7 Sep
Delta Logo
19:55 - 21:56BOS-ORD
3h 01mdirect
Delta Logo
07:00 - 10:30ORD-BOS
2h 30mdirect
₹ 10,024Delta
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Thu, 21 Aug - Sat, 23 Aug
Delta Logo
16:20 - 18:24BOS-ORD
3h 04mdirect
Delta Logo
07:00 - 10:29ORD-BOS
2h 29mdirect
₹ 10,881Delta
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KAYAK's insights & trends for Boston to O'Hare Intl flights

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

How much is a round-trip flight from Boston to Chicago O'Hare Intl Airport?

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

The average price of all round-trip flights from Boston to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

For Boston to Chicago, Thursday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Boston, the best deals are generally found on Thursday, with Wednesday being the most expensive.

What is the cheapest month to fly from Boston to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is September, where tickets cost ₹ 16,108 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is ₹ 24,247 and ₹ 24,076 respectively.

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at ₹ 14,249 on average.

How far in advance should I book a flight from Boston to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight₹ 3,941
Best time to beat the crowds (13% less expensive on average)
Most popular time to fly and prices are also 1% lower on average.
Flight from Boston to Chicago

When to book flights from Boston to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Boston to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns 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 Boston to Chicago flights

  • What is the cheapest flight from Boston to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Boston to Chicago O'Hare Intl Airport was ₹ 46 for a one-way ticket and ₹ 91 for a return.

  • 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 Chicago, also known as 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 direct flights from Boston to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and American Airlines. With an average price for the route of ₹ 19,618 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of ₹ 28,366 and an overall rating of 7.2.

  • 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 travellers 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 return 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.

KAYAK’s top tips for finding a cheap flight from Boston to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for ₹ 5,890 or less one-way and ₹ 8,858 or less round-trip.

Prefer to fly direct from Boston Logan Intl to Chicago O'Hare Intl?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop from Boston Logan Intl to Chicago O'Hare Intl.
Find which airlines fly direct from Boston Logan Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Boston Logan Intl to Chicago O'Hare Intl

Monday

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

ANA, Air New Zealand, +24 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, +23 more

ANA, Air New Zealand, +24 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

Direct returns

Chicago O'Hare Intl 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, +21 more

ANA, Air New Zealand, +22 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, +21 more

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +23 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights

Reviews of the top airlines flying from Boston to O'Hare Intl

 
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 O'Hare Intl? 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 7951 reviews
8.5Crew
7.3Food
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

4.0 OkayJames, Jul 2025MSN - ATL
Read more Delta reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything you need to know for your flight from Boston to O'Hare Intl

Information on your arrival and departure airports

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