Flights from Chicago to Pensacola

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.

Wed, Jun 18 - Sat, Jun 21

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pensacola Intl., returning Sat, Jun 21, priced at $234 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$244 Roundtrip, found 1 day ago

$244

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Pensacola Intl., returning Sat, Jun 21, priced at $244 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$246 Roundtrip, found 1 day ago

$246

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $246 found 1 day ago

Tue, Jun 10 - Sat, Jun 14

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Pensacola Intl., returning Sat, Jun 14, priced at $254 found 1 day ago

Wed, Jun 18 - Wed, Jun 25

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$255 Roundtrip, found 1 day ago

$255

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pensacola Intl., returning Wed, Jun 25, priced at $255 found 1 day ago

Sat, Jun 14 - Fri, Jun 20

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$264 Roundtrip, found 1 day ago

$264

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Pensacola Intl., returning Fri, Jun 20, priced at $264 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$269 Roundtrip, found 1 day ago

$269

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $269 found 1 day ago

Wed, Jun 18 - Fri, Jun 20

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$270 Roundtrip, found 1 day ago

$270

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pensacola Intl., returning Fri, Jun 20, priced at $270 found 1 day ago

Fri, Jun 13 - Sat, Jun 21

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$274 Roundtrip, found 1 day ago

$274

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Pensacola Intl., returning Sat, Jun 21, priced at $274 found 1 day ago

Sat, Jun 14 - Thu, Jun 26

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$275 Roundtrip, found 1 day ago

$275

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Pensacola Intl., returning Thu, Jun 26, priced at $275 found 1 day ago

Tue, Jun 17 - Fri, Jun 20

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$280 Roundtrip, found 1 day ago

$280

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Pensacola Intl., returning Fri, Jun 20, priced at $280 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$281 Roundtrip, found 1 day ago

$281

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $281 found 1 day ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$284 Roundtrip, found 1 day ago

$284

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Pensacola Intl., returning Sat, Jun 14, priced at $284 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$286 Roundtrip, found 1 day ago

$286

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pensacola Intl., returning Sun, Jun 22, priced at $286 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$287 Roundtrip, found 1 day ago

$287

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $287 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$297 Roundtrip, found 1 day ago

$297

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $297 found 1 day ago

Fri, Jun 27 - Tue, Jul 1

MDW

Midway Intl.

PNS

Pensacola Intl.

$318 Roundtrip, found 5 days ago

$318

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Jun 27 from Midway Intl. to Pensacola Intl., returning Tue, Jul 1, priced at $318 found 5 days ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$318 Roundtrip, found 1 day ago

$318

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $318 found 1 day ago

Mon, Jun 16 - Mon, Jun 23

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$429 Roundtrip, found 1 day ago

$429

Roundtrip

found 1 day ago

Select United flight, departing Mon, Jun 16 from O'Hare Intl. to Pensacola Intl., returning Mon, Jun 23, priced at $429 found 1 day ago

Sun, Jun 8 - Thu, Jun 12

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$477 Roundtrip, found 1 day ago

$477

Roundtrip

found 1 day ago

Select United flight, departing Sun, Jun 8 from O'Hare Intl. to Pensacola Intl., returning Thu, Jun 12, priced at $477 found 1 day ago