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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 April , May 2026

30 Apr - 05 May $ 252.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
13 Apr - 09 May $ 357.00
CHI
Chicago
Alaska Airlines
1 STOPS
BOS
Boston
BOS
Boston
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
13 Apr - 06 May $ 436.00
CHI
Chicago
Alaska Airlines
1 STOPS
BOS
Boston
BOS
Boston
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Boston

29 Apr - 30 Apr $ 252.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
10 Apr - 30 Apr $ 351.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
10 Apr - 30 Apr $ 351.00
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 31m
CHI - BOS
$ 84
Kiwi
Pick dates
6:00 AM - 6:00 AM
United Airlines
0 Stops
2h 25m
CHI - BOS
$ 113
Kiwi
Pick dates
6:00 AM - 6:00 AM
United Airlines
0 Stops
2h 25m
CHI - BOS
$ 113
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.