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

Tuesday, July 21st, 2026

7 round-trip options

Returning
Sun, Jul 26, 20265 Day Trip
$178 USD
Returning
Mon, Jul 27, 20266 Day Trip
$178 USD
Returning
Tue, Jul 28, 20267 Day Trip
$170 USD
Returning
Thu, Jul 30, 20269 Day Trip
$207 USD
Returning
Fri, Jul 31, 202610 Day Trip
$224 USD
Returning
Sat, Aug 1, 202611 Day Trip
$210 USD
Returning
Mon, Aug 3, 202613 Day Trip
$183 USD