Cheapest flights from Chicago
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$239 Roundtrip, found 5 hours ago
$239
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$241 Roundtrip, found 5 hours ago
$241
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$242 Roundtrip, found 5 hours ago
$242
Roundtrip
found 5 hours ago
Tue, Apr 30 - Thu, May 2
MDW
Midway Intl.
VPS
Northwest Florida Regional
$254 Roundtrip, found 3 days ago
$254
Roundtrip
found 3 days ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$276 Roundtrip, found 5 hours ago
$276
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$278 Roundtrip, found 5 hours ago
$278
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$284 Roundtrip, found 5 hours ago
$284
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$291 Roundtrip, found 5 hours ago
$291
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$293 Roundtrip, found 5 hours ago
$293
Roundtrip
found 5 hours ago
Wed, Jul 3 - Tue, Jul 9
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$293 Roundtrip, found 19 hours ago
$293
Roundtrip
found 19 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$294 Roundtrip, found 5 hours ago
$294
Roundtrip
found 5 hours ago
Wed, Jul 3 - Tue, Jul 9
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$305 Roundtrip, found 19 hours ago
$305
Roundtrip
found 19 hours ago
Tue, Apr 30 - Sat, May 4
MDW
Midway Intl.
VPS
Northwest Florida Regional
$310 Roundtrip, found 3 days ago
$310
Roundtrip
found 3 days ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$312 Roundtrip, found 5 hours ago
$312
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$313 Roundtrip, found 5 hours ago
$313
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$315 Roundtrip, found 5 hours ago
$315
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$321 Roundtrip, found 5 hours ago
$321
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$323 Roundtrip, found 5 hours ago
$323
Roundtrip
found 5 hours ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$324 Roundtrip, found 5 hours ago
$324
Roundtrip
found 5 hours ago
Wed, Jul 3 - Tue, Jul 9
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$326 Roundtrip, found 19 hours ago
$326
Roundtrip
found 19 hours ago