Chicago (ORD) to Boston (BOS) flight deal in economy from $149

Saturday, August 8th, 2026

7 round-trip options

Returning
Thu, Aug 13, 20265 Day Trip
$157 USD
Returning
Fri, Aug 14, 20266 Day Trip
$157 USD
Returning
Sat, Aug 15, 20267 Day Trip
$172 USD
Returning
Mon, Aug 17, 20269 Day Trip
$157 USD
Returning
Tue, Aug 18, 202610 Day Trip
$149 USD
Returning
Wed, Aug 19, 202611 Day Trip
$149 USD
Returning
Fri, Aug 21, 202613 Day Trip
$157 USD