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Cheap flights from Pensacola to Chicago from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago departing on 8/30. 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 Pensacola to Chicago

Cheap round-trip flights

Delta Logo
7:05 am - 11:48 amPNS-MDW
4h 43m1 stop
Delta Logo
6:00 am - 10:50 amMDW-PNS
4h 50m1 stop
$229Delta
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Wed, Aug 20 - Tue, Aug 26
Southwest Logo
2:35 pm - 7:05 pmPNS-MDW
4h 30m1 stop
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
$232Southwest
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
5:00 pm - 9:44 pmPNS-MDW
4h 44m1 stop
Delta Logo
10:31 am - 2:55 pmMDW-PNS
4h 24m1 stop
$237Delta
Find Deal
Wed, Aug 20 - Tue, Aug 26
Southwest Logo
7:35 am - 3:20 pmPNS-MDW
7h 45m1 stop
Southwest Logo
2:05 pm - 6:55 pmMDW-PNS
4h 50m1 stop
$238Southwest
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
7:50 am - 2:05 pmPNS-MDW
6h 15m1 stop
Southwest Logo
6:20 am - 3:35 pmMDW-PNS
9h 15m2 stops
$242Southwest
Find Deal
Sat, Dec 13 - Tue, Dec 16
Frontier Logo
5:21 pm - 3:53 pmPNS-MDW
22h 32m1 stop
Frontier Logo
4:29 pm - 3:31 pmMDW-PNS
23h 02m1 stop
$250Frontier
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Thu, Oct 2 - Sun, Nov 2
Southwest Logo
11:05 am - 2:45 pmPNS-MDW
3h 40m1 stop
Southwest Logo
11:45 am - 3:35 pmMDW-PNS
3h 50m1 stop
$260Southwest
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Mon, Sep 8 - Wed, Sep 10
Delta Logo
8:00 am - 11:48 amPNS-MDW
3h 48m1 stop
Delta Logo
12:43 pm - 6:54 pmMDW-PNS
6h 11m1 stop
$264Delta
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Thu, Sep 11 - Mon, Sep 15
Southwest Logo
12:30 pm - 7:25 pmPNS-MDW
6h 55m1 stop
Southwest Logo
6:25 am - 3:35 pmMDW-PNS
9h 10m2 stops
$265Southwest
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Mon, Sep 8 - Wed, Sep 10
Southwest Logo
4:25 pm - 10:25 pmPNS-MDW
6h 00m1 stop
Southwest Logo
8:50 am - 3:00 pmMDW-PNS
6h 10m1 stop
$267Southwest
Find Deal
Wed, Aug 27 - Sun, Aug 31

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Dec 13
PNS2:35 pmPensacola
4h 30m
1 stop
MDW7:05 pmChicago Midway
Dec 16
MDW10:50 amChicago Midway
4h 45m
1 stop
PNS3:35 pmPensacola
$232
Find similar
Southwest
Sep 2
PNS7:35 amPensacola
7h 45m
1 stop
MDW3:20 pmChicago Midway
Sep 9
MDW2:05 pmChicago Midway
4h 50m
1 stop
PNS6:55 pmPensacola
$238
Find similar
Southwest
Dec 13
PNS7:50 amPensacola
6h 15m
1 stop
MDW2:05 pmChicago Midway
Dec 16
MDW6:20 amChicago Midway
9h 15m
2 stops
PNS3:35 pmPensacola
$242
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Frontier flights from Pensacola to Chicago Midway Airport

Our best Frontier deals on Pensacola to Chicago Midway Airport flight tickets
Frontier
Oct 2
PNS5:21 pmPensacola
22h 32m
1 stop
MDW3:53 pmChicago Midway
Nov 2
MDW4:29 pmChicago Midway
23h 02m
1 stop
PNS3:31 pmPensacola
$250
Find similar
Frontier
Aug 1
PNS4:29 pmPensacola
28h 25m
1 stop
MDW8:54 pmChicago Midway
Aug 3
MDW2:44 pmChicago Midway
24h 50m
1 stop
PNS3:34 pmPensacola
$465
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momondo Fare Finder

 
Customize your flight search to find flights from Pensacola to Chicago Midway Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/20

7:05 am-11:48 am

1 stop4h 43m

Chicago Midway

Tue 8/26

6:00 am-10:50 am

1 stop4h 50m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 12/13

2:35 pm-7:05 pm

1 stop4h 30m

Chicago Midway

Tue 12/16

10:50 am-3:35 pm

1 stop4h 45m

$232

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/20

5:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Tue 8/26

10:31 am-2:55 pm

1 stop4h 24m

$237

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 9/2

7:35 am-3:20 pm

1 stop7h 45m

Chicago Midway

Tue 9/9

2:05 pm-6:55 pm

1 stop4h 50m

$238

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 12/13

7:50 am-2:05 pm

1 stop6h 15m

Chicago Midway

Tue 12/16

6:20 am-3:35 pm

2 stops9h 15m

$242

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 10/2

5:21 pm-3:53 pm

1 stop22h 32m

Chicago Midway

Sun 11/2

4:29 pm-3:31 pm

1 stop23h 02m

$250

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 9/8

11:05 am-2:45 pm

1 stop3h 40m

Chicago Midway

Wed 9/10

11:45 am-3:35 pm

1 stop3h 50m

$260

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 9/11

8:00 am-11:48 am

1 stop3h 48m

Chicago Midway

Mon 9/15

12:43 pm-6:54 pm

1 stop6h 11m

$264

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 9/8

12:30 pm-7:25 pm

1 stop6h 55m

Chicago Midway

Wed 9/10

6:25 am-3:35 pm

2 stops9h 10m

$265

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/27

4:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

Sun 8/31

8:50 am-3:00 pm

1 stop6h 10m

$267

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 Chicago from

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

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 Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Thursday departure recently was $327. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Pensacola because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $576.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pensacola in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $329 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $380. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pensacola to Chicago Midway flight route?

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

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

There are 1 cabin classes available to choose from on Pensacola to Chicago Midway 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 Pensacola to Chicago Midway Airport flights?

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

When to book flights from Pensacola to Chicago Midway Airport

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

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

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

Best Price Found

$109

Fastest flight time

2h 10m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $109. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $229.
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 10m
Direct flights go from Pensacola to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
Search flight deals

  • How far is Pensacola to Chicago Midway by plane?

    The distance between Pensacola and Chicago Midway is about 785.3 mi. Flights usually cover this in 3h 40m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Pensacola Airport to Chicago Midway Airport refresh daily.

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

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

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from Pensacola to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pensacola to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $216Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
8.0
7,981 reviews
Search Delta flights

  • Southwest Flights From Pensacola to Chicago Midway Airport

    Southwest is one of the most popular airlines flying from Pensacola to Chicago Midway Airport, operating 3 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago Midway Airport starts from $216 round-trip, up to an average price of $322. Our users have rated Southwest at 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.

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

Yes. momondo enables you to select and highlight flights to Chicago from Pensacola with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from Pensacola. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Pensacola to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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