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 1 day agoAugust 2026
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Rare Availability
7% of dates checked are available within 10% of the lowest price
Sunday, August 23rd, 2026
7 round-trip options
Returning
Fri, Aug 28, 2026•5 Day Trip
$170 USD
Returning
Sat, Aug 29, 2026•6 Day Trip
$157 USD
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Sun, Aug 30, 2026•7 Day Trip
$170 USD
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Mon, Aug 31, 2026•8 Day Trip
$165 USD
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Tue, Sep 1, 2026•9 Day Trip
$157 USD
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Wed, Sep 2, 2026•10 Day Trip
$157 USD
Returning
Fri, Sep 4, 2026•12 Day Trip
$203 USD