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 5 hours agoAugust 2026
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Rare Availability
9% of dates checked are available within 10% of the lowest price
Saturday, August 29th, 2026
7 round-trip options
Returning
Thu, Sep 3, 2026•5 Day Trip
$157 USD
Returning
Fri, Sep 4, 2026•6 Day Trip
$157 USD
Returning
Sat, Sep 5, 2026•7 Day Trip
$149 USD
Returning
Mon, Sep 7, 2026•9 Day Trip
$162 USD
Returning
Tue, Sep 8, 2026•10 Day Trip
$149 USD
Returning
Wed, Sep 9, 2026•11 Day Trip
$182 USD
Returning
Fri, Sep 11, 2026•13 Day Trip
$182 USD