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

Tuesday, July 7th, 2026

7 round-trip options

Returning
Sun, Jul 12, 20265 Day Trip
$277 USD
Returning
Mon, Jul 13, 20266 Day Trip
$277 USD
Returning
Tue, Jul 14, 20267 Day Trip
$277 USD
Returning
Thu, Jul 16, 20269 Day Trip
$243 USD
Returning
Fri, Jul 17, 202610 Day Trip
$243 USD
Returning
Sat, Jul 18, 202611 Day Trip
$234 USD
Returning
Mon, Jul 20, 202613 Day Trip
$243 USD