$58 Cheap flight deals from Chicago (CHI) to Gulf Breeze (PNS)

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This Weekend's Flight Deals from Chicago to Gulf Breeze

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 29 - Tue, Mar 31
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$268 Roundtrip, found 9 hours ago
$268
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sun, Mar 29 from O'Hare Intl. to Pensacola Intl., returning Tue, Mar 31, priced at $268 found 9 hours ago
Sat, Mar 28 - Sat, Apr 4
MDW
Midway Intl.
VPS
Northwest Florida Regional
$624 Roundtrip, found 5 hours ago
$624
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Mar 28 from Midway Intl. to Northwest Florida Regional, returning Sat, Apr 4, priced at $624 found 5 hours ago
Fri, Mar 27 - Fri, Apr 3
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$639 Roundtrip, found 1 day ago
$639
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Mar 27 from O'Hare Intl. to Northwest Florida Regional, returning Fri, Apr 3, priced at $639 found 1 day ago
Sat, Mar 28 - Fri, Apr 3
MDW
Midway Intl.
PNS
Pensacola Intl.
$716 Roundtrip, found 2 days ago
$716
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Mar 28 from Midway Intl. to Pensacola Intl., returning Fri, Apr 3, priced at $716 found 2 days ago

Airfares from $58 One Way, $166 Round Trip from Chicago to Gulf Breeze

Prices starting at $166 for return flights and $58 for one-way flights to Gulf Breeze were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Apr 5 - Wed, Apr 8
ORD
Chicago
PNS
Pensacola
$166 Roundtrip, found 2 hours ago
$166
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Apr 5 from Chicago to Pensacola, returning Wed, Apr 8, priced at $166 found 2 hours ago
Sun, Apr 5 - Thu, Apr 9
MDW
Chicago
PNS
Pensacola
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 5 from Chicago to Pensacola, returning Thu, Apr 9, priced at $219 found 1 day ago
Sat, May 9 - Tue, May 12
MDW
Chicago
PNS
Pensacola
$281 Roundtrip, found 1 day ago
$281
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 9 from Chicago to Pensacola, returning Tue, May 12, priced at $281 found 1 day ago
Tue, Oct 13 - Sun, Oct 18
ORD
Chicago
PNS
Pensacola
$287 Roundtrip, found 5 days ago
$287
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 13 from Chicago to Pensacola, returning Sun, Oct 18, priced at $287 found 5 days ago
Wed, Apr 29 - Wed, May 6
ORD
Chicago
PNS
Pensacola
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 29 from Chicago to Pensacola, returning Wed, May 6, priced at $293 found 1 day ago

Gulf Breeze economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Orange Beach - Gulf Shores by IHG
3.5-star property

Hotel Indigo Orange Beach - Gulf Shores by IHG

9.4/10 Exceptional! (1,011 reviews)

May 6 - May 10

4 night stay

Chicago (MDW) to Pensacola (PNS)

Southwest Airlines • Non-stop • Coach

Pensacola (PNS) to Chicago (MDW)

Frontier Airlines • Non-stop • Coach
Price was $864, price is now $675 per person
$675
per person
found 24 hours ago
We love heading down to Gulf Shores/Orange Beach the week of Thanksgiving as it’s still comfortable to do things outside. If you’re looking for a hotel with a great atmosphere, friendly staff and a place that treats you like VIP, Hotel Indigo Orange Beach, AL, is the best place to book! From the moment we walked in and Julie from the front desk greeted us to cocktails in the evening with Mike, breakfast with Cynthia and Liz and Jack providing transportation to the beach, we felt like family. Hotel Indigo was clean, beach themed decorated and still topped it off with beautiful Christmas decorations. Our room was perfect and I can’t wait until next year to have the best sleep I’ve had in years!

Reviewed on Dec 9, 2025

Oyster Bay Boutique Hotel
3.5-star property

Oyster Bay Boutique Hotel

9.6/10 Exceptional! (21 reviews)

Apr 24 - Apr 26

2 night stay

Chicago (CHI) to Pensacola (PNS)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $984, price is now $736 per person
$736
per person
found 5 hours ago
The Island Resort at Fort Walton Beach
4.0-star property

The Island Resort at Fort Walton Beach

8.4/10 Very Good! (2,997 reviews)

May 1 - May 4

3 night stay

Chicago (MDW) to Pensacola (PNS)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $933, price is now $739 per person
$739
per person
found 5 hours ago
Great beach …… travel a lot …. Room nothing special….. ocean out the door amazing….

Reviewed on Sep 10, 2025

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More About Flying To Gulf Breeze from Chicago

Route Information for Flights from Chicago to Gulf Breeze

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PNS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Gulf Breeze

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.