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

Tuesday, December 22nd, 2026

4 round-trip options

Returning
Mon, Dec 28, 20266 Day Trip
$246 USD
Returning
Tue, Dec 29, 20267 Day Trip
$225 USD
Returning
Sat, Jan 2, 202711 Day Trip
$251 USD
Returning
Tue, Jan 5, 202714 Day Trip
$290 USD