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

Wednesday, December 23rd, 2026

4 round-trip options

Returning
Tue, Dec 29, 20266 Day Trip
$246 USD
Returning
Wed, Dec 30, 20267 Day Trip
$246 USD
Returning
Sun, Jan 3, 202711 Day Trip
$267 USD
Returning
Wed, Jan 6, 202714 Day Trip
$296 USD