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Find cheap Southwest flights to Pensacola from $149

1 adult
0 bags

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Good to know

Low season

January

High season

May

Cheapest flight

$149

Average price round-trip

$427
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 3% increase in price.
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 American Airlines, Delta, American Airlines, United Airlines, Spirit Airlines, Spirit Airlines and Frontier.

  • How much is a flight to Pensacola with Southwest?

    On average, Southwest flights to Pensacola cost $215 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 Dallas Love Field Airport and cost $139.

Southwest customer reviews

8.1
Very goodBased on 4,934 verified guest reviews
7.2Food
7.7Entertainment
8.1Comfort
8.2Boarding
8.7Crew
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
A
8.0 Very good
Much better than the.last. flight on SW on Thanksgiving day
J
6.0 Okay
Ok nothing special.
A
10.0 Wonderful
Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.
M
10.0 Wonderful
Left the gate and arrived early!
L
10.0 Wonderful
Good
S
8.0 Very good
The movies using Southwest WiFi kept pausing and I had to restart multiple times.
J
10.0 Wonderful
It went well. Plane wasn't full. Will be great when assigned seating is in place
L
10.0 Wonderful
Great!
D
10.0 Wonderful
Great
D
10.0 Wonderful
Everything was great except the food. The pretzels are really crappy.
Read more about Southwest

Book Cheap flights with Southwest to Pensacola

Recent round-trip flight deals

2/2Sun
2 stopsSouthwest
7h 35mORD-PNS
2/5Wed
1 stopSouthwest
9h 50mPNS-ORD
$293
2/2Sun
2 stopsSouthwest
10h 10mORD-PNS
2/5Wed
2 stopsSouthwest
13h 10mPNS-ORD
$298
2/8Sat
2 stopsSouthwest
8h 10mDCA-PNS
2/12Wed
1 stopSouthwest
5h 45mPNS-DCA
$320
2/3Mon
2 stopsSouthwest
9h 25mMSP-PNS
2/6Thu
1 stopSouthwest
7h 50mPNS-MSP
$323
2/6Thu
1 stopSouthwest
4h 45mDCA-PNS
2/11Tue
1 stopSouthwest
8h 55mPNS-DCA
$325
2/3Mon
2 stopsSouthwest
9h 05mMSP-PNS
2/6Thu
2 stopsSouthwest
12h 05mPNS-MSP
$328
2/1Sat
1 stopSouthwest
7h 25mDCA-PNS
2/8Sat
2 stopsSouthwest
7h 55mPNS-DCA
$329
1/22Wed
2 stopsSouthwest
10h 25mDCA-PNS
1/24Fri
1 stopSouthwest
5h 25mPNS-DCA
$330
2/14Fri
1 stopSouthwest
6h 25mORD-PNS
2/18Tue
2 stopsSouthwest
17h 45mPNS-ORD
$333
2/6Thu
2 stopsSouthwest
8h 30mDEN-PNS
2/9Sun
1 stopSouthwest
7h 30mPNS-DEN
$333
2/1Sat
2 stopsSouthwest
10h 55mDCA-PNS
2/8Sat
2 stopsSouthwest
9h 25mPNS-DCA
$334
1/22Wed
2 stopsSouthwest
9h 30mDCA-PNS
1/24Fri
2 stopsSouthwest
7h 55mPNS-DCA
$335
1/6Mon
2 stopsSouthwest
9h 45mDEN-PNS
1/22Wed
2 stopsSouthwest
9h 45mPNS-DEN
$338
1/23Thu
2 stopsSouthwest
10h 25mDCA-PNS
1/27Mon
1 stopSouthwest
8h 55mPNS-DCA
$348
1/24Fri
1 stopSouthwest
10h 00mDEN-PNS
1/26Sun
2 stopsSouthwest
11h 00mPNS-DEN
$348
2/14Fri
2 stopsSouthwest
8h 20mORD-PNS
2/18Tue
2 stopsSouthwest
17h 45mPNS-ORD
$352
2/15Sat
2 stopsSouthwest
13h 40mORD-PNS
2/22Sat
1 stopSouthwest
7h 35mPNS-ORD
$353
1/23Thu
2 stopsSouthwest
10h 25mDCA-PNS
1/27Mon
2 stopsSouthwest
8h 40mPNS-DCA
$353
1/24Fri
2 stopsSouthwest
8h 25mDEN-PNS
1/26Sun
2 stopsSouthwest
11h 00mPNS-DEN
$353
1/22Wed
1 stopSouthwest
5h 20mBWI-PNS
1/24Fri
2 stopsSouthwest
8h 35mPNS-BWI
$354

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Recent one-way flight deals

2/12Wed
2 stopsSouthwest
9h 55mORD-PNS
$149
2/4Tue
1 stopSouthwest
7h 30mDCA-PNS
$153
2/17Mon
2 stopsSouthwest
8h 20mORD-PNS
$154
3/27Thu
1 stopSouthwest
9h 00mORD-PNS
$155
2/4Tue
2 stopsSouthwest
10h 25mDCA-PNS
$158
3/11Tue
2 stopsSouthwest
13h 10mORD-PNS
$160
1/7Tue
2 stopsSouthwest
8h 10mDEN-PNS
$168
2/9Sun
2 stopsSouthwest
10h 15mDCA-PNS
$177
3/2Sun
2 stopsSouthwest
8h 20mORD-PNS
$179
3/17Mon
2 stopsSouthwest
8h 25mORD-PNS
$184
12/18Wed
1 stopSouthwest
8h 55mDEN-PNS
$185
4/5Sat
2 stopsSouthwest
11h 35mORD-PNS
$190
1/4Sat
1 stopSouthwest
4h 20mDEN-PNS
$195
1/3Fri
1 stopSouthwest
4h 15mDCA-PNS
$196
1/16Thu
2 stopsSouthwest
9h 15mMSP-PNS
$198
1/2Thu
1 stopSouthwest
4h 55mDEN-PNS
$199
3/4Tue
2 stopsSouthwest
11h 30mDCA-PNS
$201
12/14Sat
1 stopSouthwest
5h 20mDEN-PNS
$203
12/18Wed
2 stopsSouthwest
10h 10mDEN-PNS
$204
12/19Thu
1 stopSouthwest
7h 55mDEN-PNS
$205

Search by stops

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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
American Airlines flights to Pensacola
Frontier flights to Pensacola
United Airlines flights to Pensacola
Spirit Airlines flights to Pensacola
Delta flights to Pensacola

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