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

Monday, December 28th, 2026

4 round-trip options

Returning
Sun, Jan 3, 20276 Day Trip
$308 USD
Returning
Mon, Jan 4, 20277 Day Trip
$287 USD
Returning
Fri, Jan 8, 202711 Day Trip
$287 USD
Returning
Mon, Jan 11, 202714 Day Trip
$287 USD