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

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
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How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
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How to find the cheapest flight from Chicago (CHI) to Boston (BOS)
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Cheap flights from Chicago to Boston in December 2025 , January 2026

25 Dec - 01 Jan $ 197.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
21 Dec - 07 Jan $ 334.00
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates
18 Dec - 18 Jan $ 349.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Boston

24 Dec - 31 Dec $ 203.00
CHI
Chicago
United Airlines
1 STOPS
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
25 Dec - 31 Dec $ 302.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
24 Dec - 31 Dec $ 327.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Boston from Chicago

1:55 PM - 1:55 PM
United Airlines
0 Stops
2h 22m
CHI - BOS
$ 99
Kiwi
Pick dates
9:12 PM - 9:12 PM
United Airlines
0 Stops
2h 33m
CHI - BOS
$ 99
Kiwi
Pick dates
1:55 PM - 1:55 PM
United Airlines
0 Stops
2h 22m
CHI - BOS
$ 164
Kiwi
Pick dates

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

Related info for your journey
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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.