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

Saturday, July 18th, 2026

7 round-trip options

Returning
Thu, Jul 23, 20265 Day Trip
$178 USD
Returning
Fri, Jul 24, 20266 Day Trip
$178 USD
Returning
Sat, Jul 25, 20267 Day Trip
$170 USD
Returning
Mon, Jul 27, 20269 Day Trip
$178 USD
Returning
Tue, Jul 28, 202610 Day Trip
$170 USD
Returning
Wed, Jul 29, 202611 Day Trip
$180 USD
Returning
Fri, Jul 31, 202613 Day Trip
$224 USD