Chicago (ORD) to Boston (BOS) flight deal in economy from $149
ORDO'Hare International Airport
Chicago, United States
BOSLogan International Airport
Boston, United States
$227 USD
-34%$149 USD
Verified about 11 hours agoOctober 2026
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Rare Availability
9% of dates checked are available within 10% of the lowest price
Tuesday, October 13th, 2026
7 round-trip options
Returning
Sun, Oct 18, 2026•5 Day Trip
$253 USD
Returning
Tue, Oct 20, 2026•7 Day Trip
$215 USD
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Wed, Oct 21, 2026•8 Day Trip
$215 USD
Returning
Thu, Oct 22, 2026•9 Day Trip
$215 USD
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Fri, Oct 23, 2026•10 Day Trip
$215 USD
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Sun, Oct 25, 2026•12 Day Trip
$236 USD
Returning
Mon, Oct 26, 2026•13 Day Trip
$215 USD