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

Wednesday, July 22nd, 2026

7 round-trip options

Returning
Mon, Jul 27, 20265 Day Trip
$157 USD
Returning
Tue, Jul 28, 20266 Day Trip
$149 USD
Returning
Wed, Jul 29, 20267 Day Trip
$159 USD
Returning
Fri, Jul 31, 20269 Day Trip
$203 USD
Returning
Sat, Aug 1, 202610 Day Trip
$189 USD
Returning
Sun, Aug 2, 202611 Day Trip
$186 USD
Returning
Tue, Aug 4, 202613 Day Trip
$149 USD