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

Tuesday, December 15th, 2026

4 round-trip options

Returning
Mon, Dec 21, 20266 Day Trip
$236 USD
Returning
Tue, Dec 22, 20267 Day Trip
$294 USD
Returning
Sat, Dec 26, 202611 Day Trip
$305 USD
Returning
Tue, Dec 29, 202614 Day Trip
$215 USD