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Find cheap Southwest flights to Pensacola from $99

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Flights Deals

Cheap Southwest Flight Deals to Pensacola

 
Here are some of the best deals found on KAYAK recently from Southwest to Pensacola that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip Southwest flight deals to Pensacola

KAYAK's recommended round-trip Southwest deals departing in the coming months to Pensacola.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
4:00 pm - 9:45 pmORD-PNS
5h 45m1 stop
Southwest Logo
6:50 am - 12:45 pmPNS-ORD
5h 55m1 stop
$197Southwest
Find Deal
Tue, Jul 15 - Tue, Jul 29
Southwest Logo
4:00 pm - 10:55 pmORD-PNS
6h 55m1 stop
Southwest Logo
6:50 am - 12:45 pmPNS-ORD
5h 55m1 stop
$232Southwest
Find Deal
Thu, Jul 3 - Tue, Jul 8
Southwest Logo
4:00 pm - 9:45 pmORD-PNS
5h 45m1 stop
Southwest Logo
8:30 am - 4:45 pmPNS-ORD
8h 15m2 stops
$243Southwest
Find Deal
Tue, Jul 15 - Tue, Jul 29
Southwest Logo
1:50 pm - 10:10 pmORD-PNS
8h 20m2 stops
Southwest Logo
8:00 am - 12:45 pmPNS-ORD
4h 45m1 stop
$252Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Southwest Logo
7:30 am - 4:10 pmORD-PNS
8h 40m1 stop
Southwest Logo
10:10 am - 11:05 pmPNS-ORD
12h 55m2 stops
$258Southwest
Find Deal
Sat, Sep 13 - Sat, Sep 20
Southwest Logo
5:10 am - 3:55 pmDEN-PNS
9h 45m1 stop
Southwest Logo
6:10 pm - 12:40 amPNS-DEN
7h 30m1 stop
$264Southwest
Find Deal
Thu, Jul 31 - Mon, Aug 4
Southwest Logo
9:40 am - 3:35 pmBWI-PNS
6h 55m1 stop
Southwest Logo
7:35 am - 12:55 pmPNS-BWI
4h 20m1 stop
$271Southwest
Find Deal
Wed, Aug 27 - Tue, Sep 2
Southwest Logo
6:15 am - 9:25 amBWI-PNS
4h 10m1 stop
Southwest Logo
12:50 pm - 10:25 pmPNS-BWI
8h 35m2 stops
$276Southwest
Find Deal
Tue, May 27 - Tue, Jun 3
Southwest Logo
4:00 pm - 10:55 pmORD-PNS
6h 55m1 stop
Southwest Logo
6:00 am - 3:00 pmPNS-ORD
9h 00m2 stops
$278Southwest
Find Deal
Fri, Jun 13 - Thu, Jun 19
Southwest Logo
10:25 am - 6:55 pmDEN-PNS
7h 30m2 stops
Southwest Logo
6:30 pm - 10:20 pmPNS-DEN
4h 50m1 stop
$279Southwest
Find Deal
Tue, Sep 9 - Wed, Sep 17
Useful Info

Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$99
Average price round-trip$375
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago O'Hare Airport to Pensacola
(price for this month)

When to book flights with Southwest to Pensacola

Average price per month
Flight prices as travel date approaches

FAQs for flying to Pensacola with Southwest

  • Which other airlines fly to Pensacola?

    Along with Southwest, you can also fly to Pensacola with Delta, American Airlines, Delta, Breeze Airways, United Airlines, Spirit Airlines, Spirit Airlines and United Airlines.

  • How much is a flight to Pensacola with Southwest?

    On average, Southwest flights to Pensacola cost $247 one-way.

  • Which airport do Southwest flights to Pensacola fly into?

    You’ll fly into Pensacola when flying to Pensacola with Southwest.

Top tips for your flights to Pensacola with Southwest

  • The cheapest flight to Pensacola with Southwest found on KAYAK in the last 2 weeks departed from Chicago Midway Airport and cost $114.

Southwest customer reviews

8.0
Very goodBased on 4,294 verified guest reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
K
8.0 Very good
Start drink service earlier. We were rushed.
J
8.0 Very good
It is southwest seat was ok. Not the most comfortable seat
H
6.0 Okay
They were more than 2 hours late.
H
10.0 Wonderful
Good
J
8.0 Very good
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
J
6.0 Okay
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
A
10.0 Wonderful
Plz don't take away free bags and free seating
D
6.0 Okay
The seats were a bit cramped and worn, but otherwise okay.
D
6.0 Okay
The seats were a bit cramped, but otherwise okay.
A
8.0 Very good
It departed late
Read more about Southwest

Everything you need to know for your flight to Pensacola

Other airlines flying to Pensacola

Flight deals from the most popular airlines with KAYAK users flying the route
Delta flights to Pensacola
American Airlines flights to Pensacola
Frontier flights to Pensacola
Spirit Airlines flights to Pensacola
United Airlines flights to Pensacola

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