$54 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, Sep 6 - Sat, Sep 12
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$337 Roundtrip, found 17 hours ago
$337
Roundtrip
found 17 hours ago
Select Delta flight, departing Sun, Sep 6 from O'Hare Intl. to Pensacola Intl., returning Sat, Sep 12, priced at $337 found 17 hours ago
Fri, Sep 4 - Mon, Sep 7
MDW
Midway Intl.
PNS
Pensacola Intl.
$451 Roundtrip, found 6 days ago
$451
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Sep 4 from Midway Intl. to Pensacola Intl., returning Mon, Sep 7, priced at $451 found 6 days ago
Sat, Sep 5 - Mon, Sep 7
RFD
Greater Rockford
PNS
Pensacola Intl.
$540 Roundtrip, found 6 days ago
$540
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Sep 5 from Greater Rockford to Pensacola Intl., returning Mon, Sep 7, priced at $540 found 6 days ago
Fri, Sep 4 - Mon, Sep 7
ORD
O'Hare Intl.
VPS
Northwest Florida Regional
$657 Roundtrip, found 17 hours ago
$657
Roundtrip
found 17 hours ago
Select Delta flight, departing Fri, Sep 4 from O'Hare Intl. to Northwest Florida Regional, returning Mon, Sep 7, priced at $657 found 17 hours ago

Airfares from $54 One Way, $97 Round Trip from Chicago to Gulf Breeze

Prices starting at $97 for return flights and $54 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.

Mon, Oct 26 - Fri, Oct 30
MDW
Chicago
VPS
Fort Walton Beach
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Oct 26 from Chicago to Fort Walton Beach, returning Fri, Oct 30, priced at $97 found 1 day ago
Thu, Sep 24 - Mon, Sep 28
ORD
Chicago
PNS
Pensacola
$222 Roundtrip, found 2 hours ago
$222
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Chicago to Pensacola, returning Mon, Sep 28, priced at $222 found 2 hours ago
Fri, Sep 18 - Sat, Sep 26
MDW
Chicago
PNS
Pensacola
$303 Roundtrip, found 6 days ago
$303
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Sep 18 from Chicago to Pensacola, returning Sat, Sep 26, priced at $303 found 6 days ago
Tue, Sep 15 - Tue, Sep 22
ORD
Chicago
PNS
Pensacola
$303 Roundtrip, found 4 days ago
$303
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 15 from Chicago to Pensacola, returning Tue, Sep 22, priced at $303 found 4 days ago
Mon, Oct 5 - Mon, Oct 19
ORD
Chicago
PNS
Pensacola
$303 Roundtrip, found 17 hours ago
$303
Roundtrip
found 17 hours ago
Select United flight, departing Mon, Oct 5 from Chicago to Pensacola, returning Mon, Oct 19, priced at $303 found 17 hours ago

Gulf Breeze economy flight packages

Price found within the past 48 hours. Click for updated prices.
Beachside Resort Hotel
2.0-star property

Beachside Resort Hotel

8/10 Very Good! (1,708 reviews)

Oct 5 - Oct 10

5 night stay

Chicago (ORD) to Pensacola (PNS)

United • Roundtrip • Coach
Price was $675, price is now $551 per person
$551
per person
found 1 day ago
The staff during check it was very nice and accommodating. Once we got to our room the ac unit was leaking in the room on the floor I requested another room and there was no problem getting another room immediately. The remote to the tv did not allow the volume to move up or down and the phone in the room didn’t work. That was a disappointment however the location was my main priority. Being directly across the street from the beach made the difference for me. I’ve stayed at this hotel several times before and still recommend it to others.

Reviewed on Aug 29, 2026

Landing Apartments Gulf Shores
3.5-star property

Landing Apartments Gulf Shores

9.2/10 Wonderful! (15 reviews)

Oct 5 - Oct 10

5 night stay

Chicago (ORD) to Pensacola (PNS)

United • Roundtrip • Coach
Price was $1,065, price is now $856 per person
$856
per person
found 1 day ago
The STAFF (Mr IVAM), was amazing and great professional. He help us all things. Good cleaning Amazing place Good neighbors. I recommend that.

Reviewed on Aug 23, 2026

The Lodge at Gulf State Park, A Hilton Hotel
4.0-star property

The Lodge at Gulf State Park, A Hilton Hotel

9.2/10 Wonderful! (1,026 reviews)

Oct 5 - Oct 10

5 night stay

Chicago (ORD) to Pensacola (PNS)

United • Roundtrip • Coach
Price was $1,402, price is now $1,159 per person
$1,159
per person
found 1 day ago
Excellent stay as usual. Many more amenities in August than January(the last time we stayed there)

Reviewed on Aug 28, 2026

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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.