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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 August , September 2026

27 Aug - 05 Sep $ 256.00
CHI
Chicago
Frontier Airlines
1 STOPS
BOS
Boston
BOS
Boston
Frontier Airlines
1 STOPS
CHI
Chicago
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31 Aug - 12 Sep $ 317.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
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28 Aug - 09 Sep $ 328.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Boston

29 Aug - 31 Aug $ 278.00
CHI
Chicago
Frontier Airlines
1 STOPS
BOS
Boston
BOS
Boston
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
28 Aug - 31 Aug $ 354.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates
29 Aug - 31 Aug $ 417.00
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
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One-way flights to Boston from Chicago

6:15 AM - 6:15 AM
United Airlines
0 Stops
2h 21m
CHI - BOS
$ 169
Kiwi
Pick dates
6:15 AM - 6:15 AM
United Airlines
0 Stops
2h 21m
CHI - BOS
$ 169
Kiwi
Pick dates
6:15 AM - 6:15 AM
United Airlines
0 Stops
2h 21m
CHI - BOS
$ 169
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.