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Cheap flights from Chicago Midway Airport to Pensacola from $82

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Pensacola departing on 4/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Pensacola

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:21 am - 3:36 pm
MDW
-
PNS
7h 15m
1 stop
Multiple Airlines Logo
4:48 pm - 10:02 pm
PNS
-
MDW
29h 14m
2 stops
$265Multiple Airlines
Thu, Apr 30 - Mon, May 4
Frontier Logo
5:05 am - 2:51 pm
MDW
-
PNS
9h 46m
1 stop
Frontier Logo
3:25 pm - 7:59 am
PNS
-
MDW
16h 34m
1 stop
$271Frontier
Sun, Apr 12 - Thu, Apr 16
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
8:00 am - 2:20 pm
PNS
-
MDW
6h 20m
1 stop
$281Southwest
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
4:52 pm - 3:53 pm
MDW
-
PNS
23h 01m
1 stop
Multiple Airlines Logo
4:48 pm - 2:12 pm
PNS
-
MDW
21h 24m
2 stops
$283Multiple Airlines
Mon, May 11 - Fri, May 15
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
8:00 am - 5:50 pm
PNS
-
MDW
9h 50m
2 stops
$286Southwest
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
8:26 am - 9:38 pm
MDW
-
PNS
13h 12m
1 stop
Multiple Airlines Logo
9:40 am - 7:31 pm
PNS
-
MDW
9h 51m
2 stops
$290Multiple Airlines
Thu, Apr 23 - Thu, Apr 30
Southwest Logo
9:50 am - 2:05 pm
MDW
-
PNS
4h 15m
1 stop
Southwest Logo
9:45 am - 4:50 pm
PNS
-
MDW
7h 05m
1 stop
$291Southwest
Wed, May 13 - Sat, May 16
Southwest Logo
10:30 am - 3:15 pm
MDW
-
PNS
4h 45m
1 stop
Southwest Logo
8:00 am - 2:35 pm
PNS
-
MDW
6h 35m
2 stops
$296Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
10:00 am - 5:20 pm
MDW
-
PNS
7h 20m
2 stops
Southwest Logo
8:00 am - 2:35 pm
PNS
-
MDW
6h 35m
2 stops
$301Southwest
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
Multiple Airlines Logo
10:12 am - 10:19 pm
PNS
-
MDW
12h 07m
2 stops
$306Multiple Airlines
Fri, Apr 17 - Mon, Apr 20

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
May 2
MDW8:10 amChicago Midway
2h 15m
PNS10:25 amPensacola
May 9
PNS8:00 amPensacola
6h 20m
1 stop
MDW2:20 pmChicago Midway
$281
Southwest
May 2
MDW8:10 amChicago Midway
2h 15m
PNS10:25 amPensacola
May 9
PNS8:00 amPensacola
9h 50m
2 stops
MDW5:50 pmChicago Midway
$286
Southwest
May 13
MDW9:50 amChicago Midway
4h 15m
1 stop
PNS2:05 pmPensacola
May 16
PNS9:45 amPensacola
7h 05m
1 stop
MDW4:50 pmChicago Midway
$291

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
May 1
MDW12:52 pmChicago Midway
3h 48m
1 stop
PNS4:40 pmPensacola
May 5
PNS8:04 amPensacola
4h 03m
1 stop
MDW12:07 pmChicago Midway
$359
Delta
Apr 12
MDW6:00 amChicago Midway
5h 15m
1 stop
PNS11:15 amPensacola
Apr 14
PNS5:26 pmPensacola
5h 02m
1 stop
MDW10:28 pmChicago Midway
$549
Delta
Apr 10
MDW12:47 pmChicago Midway
5h 56m
1 stop
PNS6:43 pmPensacola
Apr 15
PNS8:04 amPensacola
4h 03m
1 stop
MDW12:07 pmChicago Midway
$684

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Pensacola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 4/30

8:21 am-3:36 pm

1 stop7h 15m

Pensacola

Mon 5/4

4:48 pm-10:02 pm

2 stops29h 14m

$265

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 4/12

5:05 am-2:51 pm

1 stop9h 46m

Pensacola

Thu 4/16

3:25 pm-7:59 am

1 stop16h 34m

$271
Quickest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 5/2

8:10 am-10:25 am

Nonstop2h 15m

Pensacola

Sat 5/9

8:00 am-2:20 pm

1 stop6h 20m

$281

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 5/11

4:52 pm-3:53 pm

1 stop23h 01m

Pensacola

Fri 5/15

4:48 pm-2:12 pm

2 stops21h 24m

$283

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 5/2

8:10 am-10:25 am

Nonstop2h 15m

Pensacola

Sat 5/9

8:00 am-5:50 pm

2 stops9h 50m

$286

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 4/23

8:26 am-9:38 pm

1 stop13h 12m

Pensacola

Thu 4/30

9:40 am-7:31 pm

2 stops9h 51m

$290

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 5/13

9:50 am-2:05 pm

1 stop4h 15m

Pensacola

Sat 5/16

9:45 am-4:50 pm

1 stop7h 05m

$291

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 5/2

10:30 am-3:15 pm

1 stop4h 45m

Pensacola

Sat 5/9

8:00 am-2:35 pm

2 stops6h 35m

$296

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 5/2

10:00 am-5:20 pm

2 stops7h 20m

Pensacola

Sat 5/9

8:00 am-2:35 pm

2 stops6h 35m

$301

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 4/17

9:14 am-3:36 pm

1 stop6h 22m

Pensacola

Mon 4/20

10:12 am-10:19 pm

2 stops12h 07m

$306

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Pensacola from

How to get the cheapest flight ticket from Chicago Midway Airport to Pensacola

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago Midway Airport and Pensacola?

What is the cheapest day to depart on your flight to Pensacola?

On average, the least expensive day to fly to Pensacola from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $332. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $403.

What is the cheapest time of day to depart on your flight to Pensacola?

The cheapest time of day to fly to Pensacola is at noon when flights can be purchased for as low as $317. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $401. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Pensacola flight route?

Fly from Chicago Midway to Pensacola for the best Chicago Midway - Pensacola flight prices

What cabin class options are available on Chicago Midway to Pensacola flights?

There is only 1 cabin class available to choose from on Chicago Midway to Pensacola flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Pensacola flights?

You could potentially save up to 44% on your flight if you consider stops on a Chicago Midway Airport to Pensacola flight.

When to book flights from Chicago Midway Airport to Pensacola

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Pensacola according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Pensacola (MDW to PNS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Pensacola

Best Price Found

$218

Fastest flight time

2h 10m

Direct flights

Mon, Wed, Thu, Fri and Sun

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago Midway Airport in the past 72 hours is $218. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $311.
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
Direct flights go from Chicago Midway Airport to Pensacola on Monday, Wednesday, Thursday, Friday and Sunday. The only airline offering direct flights is Southwest.
There is 1 airport in Pensacola. From Chicago Midway Airport there are direct flights to Pensacola (PNS).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Pensacola

  • How far is Chicago Midway to Pensacola by plane?

    Chicago Midway and Pensacola are 785.3 mi apart from one another. A reasonable flight in good conditions will take 2h 10m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Pensacola Airport?

    Prices for flights from Chicago Midway Airport to Pensacola Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Pensacola Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Pensacola Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Pensacola Airport.

  • What documentation or ID do you need to fly to Pensacola Airport?

    The necessary travel and health documents for your Pensacola Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Pensacola?

  • What is the most popular airline from Chicago Midway Airport to Pensacola?

Best airlines flying from Chicago Midway Airport to Pensacola

Compare and see reviews for airlines that fly from Chicago Midway Airport to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
7.9
8,371 reviews
Search Delta flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,337 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Pensacola

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pensacola, operating 3 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pensacola starts from $214 round-trip, up to an average price of $360. Our users have rated Southwest at 8.0/10.

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Perdido Key
Navarre Beach
Navarre
Atmore
Gulf Breeze
Milton
Evergreen
Warrington

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Pensacola?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pensacola for you.

Can I find flights from Chicago to Pensacola with flexible booking policies on momondo?

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Pensacola?

Once all potential Chicago to Pensacola flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Pensacola right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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