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.
Mon, May 6 - Tue, Aug 6
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Tue, May 7 - Tue, Aug 6
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Fri, May 3 - Tue, Aug 6
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Thu, May 2 - Tue, Aug 6
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Sat, Jul 27 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$216 Roundtrip, found 2 days ago
$216
Roundtrip
found 2 days ago
Tue, May 7 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Tue, May 7 - Wed, Jul 31
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 days ago
Sat, May 4 - Thu, Aug 1
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Mon, May 6 - Sun, Aug 4
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Tue, Sep 24 - Thu, Oct 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$241 Roundtrip, found 1 day ago
$241
Roundtrip
found 1 day ago
Sat, Jul 27 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Tue, Apr 30 - Thu, May 2
MDW
Midway Intl.
VPS
Northwest Florida Regional
$254 Roundtrip, found 4 days ago
$254
Roundtrip
found 4 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$271 Roundtrip, found 2 days ago
$271
Roundtrip
found 2 days ago
Sat, May 4 - Sat, Aug 3
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$356 Roundtrip, found 2 days ago
$356
Roundtrip
found 2 days ago