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

Thursday, December 17th, 2026

4 round-trip options

Returning
Wed, Dec 23, 20266 Day Trip
$290 USD
Returning
Thu, Dec 24, 20267 Day Trip
$253 USD
Returning
Mon, Dec 28, 202611 Day Trip
$236 USD
Returning
Thu, Dec 31, 202614 Day Trip
$215 USD