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

Saturday, December 19th, 2026

8 round-trip options

Returning
Thu, Dec 24, 20265 Day Trip
$309 USD
Returning
Sat, Dec 26, 20267 Day Trip
$431 USD
Returning
Sun, Dec 27, 20268 Day Trip
$414 USD
Returning
Mon, Dec 28, 20269 Day Trip
$371 USD
Returning
Wed, Dec 30, 202611 Day Trip
$324 USD
Returning
Thu, Dec 31, 202612 Day Trip
$309 USD
Returning
Fri, Jan 1, 202713 Day Trip
$330 USD
Returning
Sat, Jan 2, 202714 Day Trip
$374 USD