BOS - ORD

£49 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 17/11. 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, 0 bags

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 Chicago

Thu, 4 Dec - Sun, 7 Dec
Delta Logo
16:05 - 18:02BOS-ORD
2h 57mdirect
Delta Logo
07:10 - 10:36ORD-BOS
2h 26mdirect
£90Delta
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Delta Logo
16:05 - 18:02BOS-ORD
2h 57mdirect
Delta Logo
07:10 - 10:36ORD-BOS
2h 26mdirect
£90Delta
Find Deal
Mon, 17 Nov - Thu, 19 Feb
United Airlines Logo
10:40 - 12:40BOS-ORD
3h 00mdirect
United Airlines Logo
07:30 - 10:49ORD-BOS
2h 19mdirect
£93United Airlines
Find Deal
Sun, 14 Dec - Fri, 19 Dec
Delta Logo
19:52 - 21:47BOS-ORD
2h 55mdirect
Delta Logo
10:35 - 13:59ORD-BOS
2h 24mdirect
£94Delta
Find Deal
Sat, 15 Nov - Tue, 18 Nov
United Airlines Logo
16:15 - 18:10BOS-ORD
2h 55mdirect
United Airlines Logo
12:50 - 16:10ORD-BOS
2h 20mdirect
£96United Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Delta Logo
07:30 - 09:33BOS-ORD
3h 03mdirect
Delta Logo
07:10 - 10:36ORD-BOS
2h 26mdirect
£98Delta
Find Deal
Mon, 10 Nov - Thu, 13 Nov
JetBlue Logo
15:55 - 17:55BOS-ORD
3h 00mdirect
JetBlue Logo
11:20 - 14:44ORD-BOS
2h 24mdirect
£99JetBlue
Find Deal
Thu, 15 Jan - Tue, 20 Jan
JetBlue Logo
15:35 - 17:44BOS-ORD
3h 09mdirect
JetBlue Logo
10:45 - 14:09ORD-BOS
2h 24mdirect
£100JetBlue
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Frontier Logo
11:28 - 22:24BOS-ORD
11h 56m1 stop
Frontier Logo
06:00 - 12:02ORD-BOS
5h 02m1 stop
£109Frontier
Find Deal
Mon, 10 Nov - Mon, 10 Nov
Southwest Logo
05:00 - 12:15BOS-ORD
8h 15m1 stop
Southwest Logo
13:45 - 23:15ORD-BOS
8h 30m1 stop
£131Southwest
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom comfort.
Use the FlyLogan app for gate info and dining options.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Delta
Cheapest • from £90 (return)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 17% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
£90
Overall average: £215
Delta
Thu 4/12Sun 7/12
BOS - ORD • Direct
Cheapest one-way flight
£49
Typical prices: £74-£165
JetBlue
Mon 17/11
BOS - ORD • Direct
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for Boston to Chicago flights

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’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.

If you are looking for a flight deal from Boston to Chicago, look for departures on Thursdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Monday is 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 £157 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is £215 and £209 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 £123 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 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Boston to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Royal Jordanian

Royal Jordanian's economy class offers well-padded seats with good legroom and a hot meal service.


Royal Jordanian's business class on A320s offers comfortable recliners with 2x2 seating arrangement.

Read more about Royal Jordanianby Gabriel Leigh
United Airlines

United's Premier Access offers priority check-in and boarding, ideal for business travelers.


United's Economy Plus seats offer up to six inches more legroom, enhancing comfort on short flights.

Read more about United Airlinesby Stefanie Waldek
Airports
BOS

Use the FlyLogan app for gate info, flight status, and ordering ahead at airport restaurants. Reserve parking in advance during busy travel times.

Read more about BOSby Blane Bachelor
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays and offering free transfers to other lines.

Read more about ORDby Stefanie Waldek
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on Royal Jordanian

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specialising in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favourite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history.

Read more

Good to know - Cheap tickets from Boston to Chicago

Low seasonJanuary
Cheapest flight£49
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly (9% more expensive on average)
Flight from Boston to Chicago

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 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 £49 for a one-way ticket and £90 for a return.

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

    On your way to Chicago, you’ll fly out from Boston Logan Intl. You’ll be landing at 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 is the only airline alliance operating flights between Boston and Chicago.

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

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

  • 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.

Prefer to fly direct from Boston to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct 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

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Tuesday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Wednesday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Thursday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Friday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Saturday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Sunday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Tuesday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Wednesday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Thursday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Friday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Saturday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

Sunday

American Airlines, Delta, JetBlue, +1 more

American Airlines, Delta, +2 more

See more direct flights

Reviews of the top airline flying 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.
7.2
American AirlinesOverall score based on 11034 reviews
6.9Entertainment
7.5Boarding
6.4Food
8.0Crew
7.2Comfort
Airline reviews

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

8.0 ExcellentKrishna, Oct 2025BOS - ORD
Read more American Airlines reviews

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

Everything you need to know for your flight from Boston to Chicago

Information on your arrival and departure airports

Boston (BOS)
O'Hare Intl (ORD)

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