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

Friday, December 18th, 2026

4 round-trip options

Returning
Thu, Dec 24, 20266 Day Trip
$275 USD
Returning
Fri, Dec 25, 20267 Day Trip
$246 USD
Returning
Tue, Dec 29, 202611 Day Trip
$236 USD
Returning
Fri, Jan 1, 202714 Day Trip
$236 USD