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 26/2. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest return fare
£98
Overall average: £201
JetBlue
Tue 7/4Wed 8/4
BOS - ORD • Direct
Cheapest one-way flight
£49
Typical prices: £67-£144
United Airlines
Thu 26/2
BOS - ORD • Direct
Our travellers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
JetBlue
Cheapest • from £98 (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 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 17% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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

Tue, 7 Apr - Wed, 8 Apr
JetBlue Logo
07:10 - 09:10
BOS
-
ORD
3h 00mdirect
JetBlue Logo
10:00 - 13:27
ORD
-
BOS
2h 27mdirect
£98JetBlue
Wed, 25 Feb - Sat, 28 Feb
Delta Logo
07:15 - 09:28
BOS
-
ORD
3h 13mdirect
Delta Logo
07:05 - 10:37
ORD
-
BOS
2h 32mdirect
£99Delta
Wed, 11 Feb - Sun, 15 Feb
Delta Logo
16:10 - 18:19
BOS
-
ORD
3h 09mdirect
Delta Logo
07:05 - 10:37
ORD
-
BOS
2h 32mdirect
£99Delta
Wed, 25 Feb - Mon, 2 Mar
Delta Logo
19:45 - 21:48
BOS
-
ORD
3h 03mdirect
Delta Logo
17:37 - 23:26
ORD
-
BOS
4h 49m
1 stop
£100Delta
Sat, 28 Feb - Tue, 3 Mar
Delta Logo
16:58 - 20:44
BOS
-
ORD
4h 46m
1 stop
Delta Logo
07:10 - 13:19
ORD
-
BOS
5h 09m
1 stop
£101Delta
Sat, 28 Feb - Mon, 2 Mar
Delta Logo
11:50 - 18:01
BOS
-
ORD
7h 11m
1 stop
Delta Logo
17:37 - 23:26
ORD
-
BOS
4h 49m
1 stop
£101Delta
Mon, 9 Feb - Thu, 12 Feb
Delta Logo
20:25 - 22:29
BOS
-
ORD
3h 04mdirect
Delta Logo
07:05 - 10:37
ORD
-
BOS
2h 32mdirect
£102Delta
Mon, 9 Feb - Thu, 5 Mar
Delta Logo
20:25 - 22:29
BOS
-
ORD
3h 04mdirect
Delta Logo
06:00 - 13:19
ORD
-
BOS
6h 19m
1 stop
£103Delta
Thu, 5 Mar - Mon, 9 Mar
United Airlines Logo
08:15 - 10:20
BOS
-
ORD
3h 05mdirect
United Airlines Logo
21:15 - 00:35
ORD
-
BOS
2h 20mdirect
£104United Airlines
Tue, 10 Feb - Fri, 13 Feb
United Airlines Logo
06:00 - 08:04
BOS
-
ORD
3h 04mdirect
United Airlines Logo
07:30 - 10:49
ORD
-
BOS
2h 19mdirect
£104United Airlines
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 Saturday, as it's usually the priciest day. When flying back from Chicago, Sunday 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 January, where tickets cost £150 (return) on average. On the other hand, the most expensive months are April and October, where the average cost of round-trip tickets is £201 and £194 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 £118 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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Boston to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on Royal Jordanian

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 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 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 (17% less expensive on average)
Most popular time to fly (5% 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 £98 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.

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

  • Looking for a cheap flight from Chicago to Boston? 25% of our users found flights on this route for £118 or less one-way.

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 11206 reviews
7.2Comfort
8.0Crew
7.5Boarding
6.4Food
6.9Entertainment
Airline reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

10.0 Excellentaras, Jan 2026
PIT - ORD
Read more American Airlines reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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.

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)