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

Friday, December 25th, 2026

4 round-trip options

Returning
Thu, Dec 31, 20266 Day Trip
$215 USD
Returning
Fri, Jan 1, 20277 Day Trip
$215 USD
Returning
Tue, Jan 5, 202711 Day Trip
$215 USD
Returning
Fri, Jan 8, 202714 Day Trip
$215 USD