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

Thursday, July 23rd, 2026

7 round-trip options

Returning
Tue, Jul 28, 20265 Day Trip
$157 USD
Returning
Wed, Jul 29, 20266 Day Trip
$167 USD
Returning
Thu, Jul 30, 20267 Day Trip
$194 USD
Returning
Sat, Aug 1, 20269 Day Trip
$197 USD
Returning
Sun, Aug 2, 202610 Day Trip
$194 USD
Returning
Mon, Aug 3, 202611 Day Trip
$170 USD
Returning
Wed, Aug 5, 202613 Day Trip
$157 USD