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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)
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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 March , April 2026

30 Mar - 02 Apr $ 147.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
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10 Mar - 09 Apr $ 305.00
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates
10 Mar - 09 Apr $ 5,678.00
CHI
Chicago
Spirit Airlines
DIRECT
BOS
Boston
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Boston

24 Mar - 31 Mar $ 231.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
Pick dates
10 Mar - 31 Mar $ 5,611.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
BOS
Boston
BOS
Boston
Hawaiian Airlines
DIRECT
CHI
Chicago
Pick dates
10 Mar - 31 Mar $ 10,914.00
CHI
Chicago
Hawaiian Airlines
DIRECT
BOS
Boston
BOS
Boston
Hawaiian 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
$ 79
Kiwi
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7:30 AM - 7:30 AM
United Airlines
0 Stops
2h 19m
CHI - BOS
$ 83
Kiwi
Pick dates
7:30 AM - 7:30 AM
United Airlines
0 Stops
2h 20m
CHI - BOS
$ 83
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.