BOS - ORD

₹ 6,038 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 21/9. 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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Flight Deals

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, 4 Sep - Sun, 7 Sep
United Airlines Logo
15:15 - 17:05BOS-ORD
2h 50mdirect
United Airlines Logo
06:30 - 09:56ORD-BOS
2h 26mdirect
₹ 11,114United Airlines
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Wed, 17 Sep - Tue, 23 Sep
JetBlue Logo
07:00 - 08:56BOS-ORD
2h 56mdirect
JetBlue Logo
09:51 - 13:20ORD-BOS
2h 29mdirect
₹ 11,989JetBlue
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Delta Logo
14:55 - 16:52BOS-ORD
2h 57mdirect
Delta Logo
07:00 - 10:30ORD-BOS
2h 30mdirect
₹ 12,076Delta
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Thu, 4 Sep - Sun, 7 Sep
Delta Logo
14:55 - 16:52BOS-ORD
2h 57mdirect
Delta Logo
07:00 - 10:30ORD-BOS
2h 30mdirect
₹ 12,164Delta
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Fri, 19 Sep - Mon, 22 Sep
United Airlines Logo
06:10 - 08:05BOS-ORD
2h 55mdirect
United Airlines Logo
21:15 - 00:45ORD-BOS
2h 30mdirect
₹ 13,126United Airlines
Find Deal
Mon, 8 Sep - Fri, 12 Sep
United Airlines Logo
20:27 - 22:15BOS-ORD
2h 48mdirect
United Airlines Logo
21:15 - 00:45ORD-BOS
2h 30mdirect
₹ 13,214United Airlines
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Wed, 1 Oct - Mon, 6 Oct
JetBlue Logo
16:40 - 18:55BOS-ORD
3h 15mdirect
JetBlue Logo
19:13 - 22:46ORD-BOS
2h 33mdirect
₹ 13,739JetBlue
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Fri, 12 Sep - Mon, 15 Sep
Southwest Logo
05:00 - 16:25BOS-ORD
12h 25m1 stop
Southwest Logo
13:50 - 22:15ORD-BOS
7h 25m1 stop
₹ 14,177Southwest
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Wed, 10 Sep - Fri, 12 Sep
Spirit Airlines Logo
15:00 - 22:48BOS-ORD
8h 48m1 stop
Spirit Airlines Logo
11:57 - 23:57ORD-BOS
11h 00m1 stop
₹ 15,052Spirit Airlines
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Sat, 13 Dec - Wed, 17 Dec
Southwest Logo
12:50 - 21:50BOS-ORD
10h 00m2 stops
Southwest Logo
13:45 - 22:15ORD-BOS
7h 30m1 stop
₹ 19,252Southwest
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Booking Insights

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.

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 Tuesday, with Sunday 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 ₹ 16,802 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is ₹ 24,765 and ₹ 24,678 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 ₹ 14,554 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, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight₹ 6,038
Best time to beat the crowds (14% less expensive on average)
Most popular time to fly (14% more expensive 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 ₹ 69 for a one-way ticket and ₹ 127 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, SkyTeam, and Star Alliance 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 ₹ 19,860 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of ₹ 28,972 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 ₹ 7,744 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 France, Air New Zealand, +24 more

ANA, Air France, +25 more

Tuesday

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

ANA, Air France, +24 more

Wednesday

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

ANA, Air France, +24 more

Thursday

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

ANA, Air France, +25 more

Friday

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

ANA, Air France, +25 more

Saturday

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

ANA, Air France, +23 more

Sunday

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

ANA, Air France, +25 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

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

ANA, Air France, +24 more

Tuesday

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

ANA, Air France, +24 more

Wednesday

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

ANA, Air France, +24 more

Thursday

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

ANA, Air France, +24 more

Friday

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

ANA, Air France, +23 more

Saturday

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

ANA, Air New Zealand, +24 more

Sunday

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

ANA, Air France, +24 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.
7.9
DeltaOverall score based on 7981 reviews
7.9Entertainment
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

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.

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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