Chicago (ORD) to Boston (BOS) flight deal in economy from $187

Wednesday, June 24th, 2026

10 round-trip options

Returning
Mon, Jun 29, 20265 Day Trip
$196 USD
Returning
Tue, Jun 30, 20266 Day Trip
$187 USD
Returning
Wed, Jul 1, 20267 Day Trip
$187 USD
Returning
Thu, Jul 2, 20268 Day Trip
$196 USD
Returning
Fri, Jul 3, 20269 Day Trip
$196 USD
Returning
Sat, Jul 4, 202610 Day Trip
$187 USD
Returning
Sun, Jul 5, 202611 Day Trip
$196 USD
Returning
Mon, Jul 6, 202612 Day Trip
$217 USD
Returning
Tue, Jul 7, 202613 Day Trip
$187 USD
Returning
Wed, Jul 8, 202614 Day Trip
$187 USD