Boston (BOS) to Chicago (ORD) flight deal in economy from $149
BOSLogan International Airport
Boston, United States
ORDO'Hare International Airport
Chicago, United States
$230 USD
-35%$149 USD
Verified about 21 hours agoDecember 2026
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Rare Availability
7% of dates checked are available within 10% of the lowest price
Friday, December 18th, 2026
8 round-trip options
Returning
Wed, Dec 23, 2026•5 Day Trip
$378 USD
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Fri, Dec 25, 2026•7 Day Trip
$347 USD
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Sat, Dec 26, 2026•8 Day Trip
$479 USD
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Sun, Dec 27, 2026•9 Day Trip
$462 USD
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Tue, Dec 29, 2026•11 Day Trip
$421 USD
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Wed, Dec 30, 2026•12 Day Trip
$372 USD
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Thu, Dec 31, 2026•13 Day Trip
$357 USD
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Fri, Jan 1, 2027•14 Day Trip
$378 USD