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Cheap flights from Chicago Midway Airport to Pensacola from $88

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 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Southwest Logo
6:10 am - 3:15 pm
MDW
-
PNS
9h 05m2 stops
Southwest Logo
7:45 am - 1:30 pm
PNS
-
MDW
5h 45m2 stops
$213Southwest
Tue, Feb 24 - Sat, Feb 28
Southwest Logo
6:00 am - 9:50 am
MDW
-
PNS
3h 50m1 stop
Southwest Logo
4:25 pm - 8:10 pm
PNS
-
MDW
3h 45m1 stop
$218Southwest
Wed, Feb 18 - Mon, Feb 23
Delta Logo
6:00 am - 12:30 pm
MDW
-
PNS
6h 30m1 stop
Delta Logo
5:00 pm - 10:31 pm
PNS
-
MDW
5h 31m1 stop
$220Delta
Mon, Feb 23 - Sat, Feb 28
Southwest Logo
12:35 pm - 9:55 pm
MDW
-
PNS
9h 20m2 stops
Southwest Logo
5:20 pm - 7:35 pm
PNS
-
MDW
2h 15mnonstop
$224Southwest
Sat, Mar 21 - Wed, Mar 25
Southwest Logo
5:55 am - 11:20 am
MDW
-
PNS
5h 25m1 stop
Southwest Logo
7:45 am - 1:30 pm
PNS
-
MDW
5h 45m2 stops
$225Southwest
Mon, Feb 23 - Sat, Feb 28
Multiple Airlines Logo
7:45 am - 3:54 pm
MDW
-
PNS
32h 09m2 stops
Multiple Airlines Logo
6:37 pm - 2:55 pm
PNS
-
MDW
20h 18m1 stop
$226Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
Southwest Logo
10:10 am - 4:45 pm
MDW
-
PNS
6h 35m1 stop
Southwest Logo
9:40 am - 2:25 pm
PNS
-
MDW
4h 45m1 stop
$227Southwest
Fri, Apr 3 - Sat, Apr 11
Delta Logo
6:30 am - 12:09 pm
MDW
-
PNS
5h 39m1 stop
Delta Logo
6:00 am - 9:56 am
PNS
-
MDW
3h 56m1 stop
$228Delta
Wed, Apr 15 - Sat, Apr 18
Delta Logo
6:40 pm - 11:11 pm
MDW
-
PNS
4h 31m1 stop
Delta Logo
6:00 am - 10:21 am
PNS
-
MDW
4h 21m1 stop
$229Delta
Fri, Feb 27 - Sat, Mar 7
Southwest Logo
12:35 pm - 9:55 pm
MDW
-
PNS
9h 20m2 stops
Southwest Logo
9:40 am - 2:25 pm
PNS
-
MDW
4h 45m1 stop
$231Southwest
Sat, Apr 4 - Sat, Apr 11

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Mar 21
MDW12:35 pmChicago Midway
9h 20m
2 stops
PNS9:55 pmPensacola
Mar 25
PNS5:20 pmPensacola
2h 15m
MDW7:35 pmChicago Midway
$224
Find similar
Southwest
Apr 4
MDW4:55 pmChicago Midway
2h 15m
PNS7:10 pmPensacola
Apr 11
PNS9:40 amPensacola
9h 40m
1 stop
MDW7:20 pmChicago Midway
$225
Find similar
Southwest
Apr 3
MDW11:40 amChicago Midway
5h 05m
1 stop
PNS4:45 pmPensacola
Apr 11
PNS9:40 amPensacola
4h 45m
1 stop
MDW2:25 pmChicago Midway
$227
Find similar

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Feb 18
MDW12:45 pmChicago Midway
5h 57m
1 stop
PNS6:42 pmPensacola
Feb 24
PNS6:00 amPensacola
5h 59m
1 stop
MDW11:59 amChicago Midway
$228
Find similar
Delta
Feb 27
MDW6:00 amChicago Midway
6h 30m
1 stop
PNS12:30 pmPensacola
Mar 6
PNS6:00 amPensacola
3h 54m
1 stop
MDW9:54 amChicago Midway
$229
Find similar
Delta
Feb 18
MDW12:45 pmChicago Midway
5h 57m
1 stop
PNS6:42 pmPensacola
Feb 23
PNS5:48 pmPensacola
4h 43m
1 stop
MDW10:31 pmChicago Midway
$245
Find similar

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 January 6, 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

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 2/24

6:10 am-3:15 pm

2 stops9h 05m

Pensacola

Sat 2/28

7:45 am-1:30 pm

2 stops5h 45m

$213

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Mon 2/23

4:25 pm-8:10 pm

1 stop3h 45m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 2/23

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Sat 2/28

5:00 pm-10:31 pm

1 stop5h 31m

$220

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 3/21

12:35 pm-9:55 pm

2 stops9h 20m

Pensacola

Wed 3/25

5:20 pm-7:35 pm

Nonstop2h 15m

$224

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 2/23

5:55 am-11:20 am

1 stop5h 25m

Pensacola

Sat 2/28

7:45 am-1:30 pm

2 stops5h 45m

$225

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/13

7:45 am-3:54 pm

2 stops32h 09m

Pensacola

Fri 2/20

6:37 pm-2:55 pm

1 stop20h 18m

$226

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 4/3

10:10 am-4:45 pm

1 stop6h 35m

Pensacola

Sat 4/11

9:40 am-2:25 pm

1 stop4h 45m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 4/15

6:30 am-12:09 pm

1 stop5h 39m

Pensacola

Sat 4/18

6:00 am-9:56 am

1 stop3h 56m

$228

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/27

6:40 pm-11:11 pm

1 stop4h 31m

Pensacola

Sat 3/7

6:00 am-10:21 am

1 stop4h 21m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 4/4

12:35 pm-9:55 pm

2 stops9h 20m

Pensacola

Sat 4/11

9:40 am-2:25 pm

1 stop4h 45m

$231

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 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 Tuesday. momondo users have found tickets for Tuesday departures for as low as $325. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $387.

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 $323. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $479. 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Pensacola.

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

$319

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Pensacola

1 airport
The best flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $319
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
Direct flights go from Chicago Midway Airport to Pensacola every day.
There is 1 airport in Pensacola. From Chicago Midway Airport there are direct flights to Pensacola (PNS).
Search flight deals

  • 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
8,018 reviews
Search Delta flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,248 reviews
Search Southwest flights

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
Navarre Beach
Atmore
Milton
Gulf Breeze
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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