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

Friday, December 11th, 2026

4 round-trip options

Returning
Thu, Dec 17, 20266 Day Trip
$287 USD
Returning
Fri, Dec 18, 20267 Day Trip
$347 USD
Returning
Tue, Dec 22, 202611 Day Trip
$294 USD
Returning
Fri, Dec 25, 202614 Day Trip
$225 USD