Cheap flights from Boston to Chicago

Round-trip
Economy
Boston (BOS)
Chicago (CHI)
Fri 7/23
Fri 7/30
Any month
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Flight information for Boston to Chicago
(BOS to CHI)

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Best Price Found$54The best flight deal from Boston to Chicago found on momondo in the last 72 hours is $54
Fastest flight time2h 50mThe fastest flight from Boston to Chicago takes 2h 50m
Direct flightsTh, Fr, Sa and SuDirect flights go from Boston to Chicago on Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

August
The cheapest time of year to fly to Chicago from Boston is August. Most expensive is December

What is the cheapest day to depart Boston for Chicago?

Saturday
The cheapest day of the week is typically Saturday. The most expensive is typically Sunday

When is the cheapest time to fly from Boston to Chicago?

at noon
Boston to Chicago flights are approximately 36% more expensive in the afternoon than at noon

What is the cheapest airline that flies to Chicago from Boston?

Spirit Airlines
Spirit Airlines, Envoy Air, and Delta are the most popular carriers operating from Boston to Chicago

What is the cheapest Boston to Chicago flight route?

Boston Logan Intl - Chicago O'Hare Intl
Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices

How far in advance should you book Boston to Chicago flights?

3 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 3 days to departure
60
Days before departure
0

Easily compare round-trip flights from Boston to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
Spirit Airlines
Sep 18
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 22
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 14
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Sep 14
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl

Find the cheapest one-way flights from Boston to Chicago

If you're looking for one-way flights from Boston to Chicago, view some of our deals below provided by Spirit Airlines
Spirit Airlines
Sep 22
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Spirit Airlines
Sep 11
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
AirlineRatingFree CancellationPrice
Spirit Airlines
PriceFrom $56
Free Cancellation
Rating
7.0
7.4

Boarding

6.7

Comfort

7.6

Crew

6.3

Entertainment

6.4

Food

Reviews

Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.

Cons: Mostly everything.

1 / 10
Delta
PriceFrom $68
Free Cancellation
Rating
8.1
8.3

Boarding

8.4

Comfort

8.3

Crew

7.9

Entertainment

8.1

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
JetBlue
PriceFrom $71
Free Cancellation
Rating
7.9
8.2

Boarding

8.1

Comfort

8.4

Crew

7.8

Entertainment

7.5

Food

Reviews

Pros: Wayne at the DCA Airport was gracious and amazing.

Cons: The planes still aren’t clean. Pretty sure something was growing on the seat in front of me.

1 / 10
American Airlines
PriceFrom $77
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.9

Crew

7.0

Entertainment

6.8

Food

Reviews

Pros: Delayed flight no reasons seems like American Airlines don’t know what to do in these situations

Cons: I believe this airlines should have figured the answer to this question by now.

1 / 10
United Airlines
PriceFrom $80
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Southwest
PriceFrom $185
Free Cancellation
Rating
8.4
8.6

Boarding

8.5

Comfort

8.8

Crew

7.6

Entertainment

7.8

Food

Reviews

Pros: The plane was new and the seats were nice.

1 / 10

Are airlines flying from Boston Logan Intl to Chicago offering flexible cancellation due to COVID-19?

Due to the global impact of COVID-19, some of our airline partners operating flights from Boston Logan Intl to Chicago, such as United Airlines, American Airlines, and JetBlue may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.


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