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

Tuesday, November 17th, 2026

8 round-trip options

Returning
Sun, Nov 22, 20265 Day Trip
$206 USD
Returning
Mon, Nov 23, 20266 Day Trip
$206 USD
Returning
Tue, Nov 24, 20267 Day Trip
$236 USD
Returning
Thu, Nov 26, 20269 Day Trip
$206 USD
Returning
Fri, Nov 27, 202610 Day Trip
$206 USD
Returning
Sat, Nov 28, 202611 Day Trip
$412 USD
Returning
Mon, Nov 30, 202613 Day Trip
$406 USD
Returning
Tue, Dec 1, 202614 Day Trip
$206 USD