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

Friday, July 31st, 2026

7 round-trip options

Returning
Wed, Aug 5, 20265 Day Trip
$157 USD
Returning
Thu, Aug 6, 20266 Day Trip
$194 USD
Returning
Fri, Aug 7, 20267 Day Trip
$235 USD
Returning
Sun, Aug 9, 20269 Day Trip
$211 USD
Returning
Mon, Aug 10, 202610 Day Trip
$210 USD
Returning
Tue, Aug 11, 202611 Day Trip
$157 USD
Returning
Thu, Aug 13, 202613 Day Trip
$165 USD