Earn point on your loyalty program!arrow arc left

Cheap flights from Chicago (CHI) to Boston (BOS)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Chicago to Boston in January , February 2026

21 Jan - 04 Feb $ 176.00
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates
29 Jan - 02 Feb $ 204.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
21 Jan - 06 Feb $ 297.00
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Boston

21 Jan - 31 Jan $ 187.00
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates
23 Jan - 31 Jan $ 205.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
15 Jan - 31 Jan $ 205.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Boston from Chicago

7:30 AM - 7:30 AM
United Airlines
0 Stops
2h 22m
CHI - BOS
$ 68
Kiwi
Pick dates
7:30 AM - 7:30 AM
United Airlines
0 Stops
2h 22m
CHI - BOS
$ 68
Kiwi
Pick dates
1:55 PM - 1:55 PM
United Airlines
0 Stops
2h 24m
CHI - BOS
$ 68
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.