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

Saturday, December 19th, 2026

4 round-trip options

Returning
Fri, Dec 25, 20266 Day Trip
$272 USD
Returning
Sat, Dec 26, 20267 Day Trip
$351 USD
Returning
Wed, Dec 30, 202611 Day Trip
$262 USD
Returning
Sat, Jan 2, 202714 Day Trip
$288 USD