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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 November , December 2026

23 Nov - 15 Dec $ 254.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
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12 Nov - 05 Dec $ 336.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates
12 Nov - 09 Dec $ 336.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Boston

23 Nov - 30 Nov $ 357.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates
13 Nov - 30 Nov $ 437.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates
12 Nov - 30 Nov $ 453.00
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
Pick dates

One-way flights to Boston from Chicago

5:30 PM - 5:30 PM
JetBlue Airways
0 Stops
2h 29m
CHI - BOS
$ 130
Kiwi
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8:15 PM - 8:15 PM
JetBlue Airways
0 Stops
2h 44m
CHI - BOS
$ 211
Kiwi
Pick dates
8:15 PM - 8:15 PM
JetBlue Airways
0 Stops
2h 44m
CHI - BOS
$ 211
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.