Cheap flights from Chicago to Boston

Round-trip
Economy
Chicago (CHI)
Boston (BOS)
Sat 7/24
Sat 7/31
Any month
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Flight information for Chicago to Boston
(CHI to BOS)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston
Best Price Found$52The best flight deal from Chicago to Boston found on momondo in the last 72 hours is $52
Fastest flight time2h 21mThe fastest flight from Chicago to Boston takes 2h 21m
Direct flightsMo, Tu, We, Fr, Sa and SuDirect flights go from Chicago to Boston on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
Airports in Boston1 airportThere is 1 airport near Boston: Boston Logan Intl (BOS)

How to get the cheapest flight ticket from Chicago to Boston

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 Chicago to Boston?

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

What is the cheapest day to depart Chicago for Boston?

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

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

at noon
Chicago to Boston flights are approximately 32% more expensive in the afternoon than at noon

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

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

What is the cheapest Chicago to Boston flight route?

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

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

5 days before
The cheapest time to buy a flight from Chicago to Boston is approximately 5 days to departure
60
Days before departure
0

Easily compare round-trip flights from Chicago to Boston

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 Chicago to Boston by changing tabs
Spirit Airlines
Oct 2
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Oct 6
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Spirit Airlines
Sep 14
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Sep 18
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Spirit Airlines
Sep 18
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Sep 22
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Boston

If you're looking for one-way flights from Chicago to Boston, view some of our deals below provided by Spirit Airlines
Spirit Airlines
Sep 18
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Oct 5
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines
Sep 22
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
AirlineRatingFree CancellationPrice
Delta
PriceFrom $48
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
Spirit Airlines
PriceFrom $54
Free Cancellation
Rating
7.0
7.3

Boarding

6.7

Comfort

7.5

Crew

6.2

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
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
United Airlines
PriceFrom $76
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
American Airlines
PriceFrom $76
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
Southwest
PriceFrom $189
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 Chicago to Boston Logan Intl offering flexible cancellation due to COVID-19?

Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Boston Logan Intl, such as American Airlines, United Airlines, and Spirit Airlines 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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