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

Friday, July 24th, 2026

7 round-trip options

Returning
Wed, Jul 29, 20265 Day Trip
$167 USD
Returning
Thu, Jul 30, 20266 Day Trip
$194 USD
Returning
Fri, Jul 31, 20267 Day Trip
$211 USD
Returning
Sun, Aug 2, 20269 Day Trip
$194 USD
Returning
Mon, Aug 3, 202610 Day Trip
$170 USD
Returning
Tue, Aug 4, 202611 Day Trip
$157 USD
Returning
Thu, Aug 6, 202613 Day Trip
$194 USD