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Cheap flights from Pensacola to Chicago from $90

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 1/14. 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 Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:59 pm - 7:07 pm
PNS
-
MDW
25h 08m2 stops
Multiple Airlines Logo
7:30 am - 5:42 pm
MDW
-
PNS
10h 12m1 stop
$210Multiple Airlines
Tue, Feb 17 - Sun, Feb 22
Delta Logo
5:54 pm - 10:07 pm
PNS
-
MDW
4h 13m1 stop
Delta Logo
6:00 am - 12:35 pm
MDW
-
PNS
6h 35m1 stop
$229Delta
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
5:33 pm - 7:27 am
PNS
-
MDW
13h 54m2 stops
Multiple Airlines Logo
10:07 am - 4:37 pm
MDW
-
PNS
6h 30m1 stop
$240Multiple Airlines
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
5:33 pm - 7:58 pm
PNS
-
MDW
26h 25m1 stop
Multiple Airlines Logo
9:15 am - 7:35 am
MDW
-
PNS
22h 20m2 stops
$246Multiple Airlines
Sun, Jan 25 - Sat, Feb 14
Southwest Logo
7:05 am - 1:00 pm
PNS
-
MDW
5h 55m1 stop
Southwest Logo
5:25 am - 9:50 am
MDW
-
PNS
4h 25m1 stop
$249Southwest
Tue, Feb 17 - Sun, Feb 22
Southwest Logo
4:25 pm - 8:10 pm
PNS
-
MDW
3h 45m1 stop
Southwest Logo
9:20 am - 4:05 pm
MDW
-
PNS
6h 45m1 stop
$255Southwest
Sun, Jan 25 - Sat, Feb 14
Southwest Logo
9:40 am - 2:30 pm
PNS
-
MDW
4h 50m1 stop
Southwest Logo
7:25 am - 4:15 pm
MDW
-
PNS
8h 50m2 stops
$274Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
11:15 am - 9:05 pm
PNS
-
MDW
9h 50m2 stops
Southwest Logo
10:30 am - 5:20 pm
MDW
-
PNS
6h 50m2 stops
$314Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
9:40 am - 2:30 pm
PNS
-
MDW
4h 50m1 stop
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
$343Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
7:05 am - 5:35 pm
PNS
-
MDW
10h 30m2 stops
Southwest Logo
5:00 am - 4:05 pm
MDW
-
PNS
11h 05m2 stops
$346Southwest
Sun, Jan 25 - Sat, Feb 14

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Jan 16
PNS5:54 pmPensacola
4h 13m
1 stop
MDW10:07 pmChicago Midway
Jan 19
MDW6:00 amChicago Midway
6h 35m
1 stop
PNS12:35 pmPensacola
$229
Find similar
Delta
Jan 1
PNS8:20 amPensacola
6h 24m
1 stop
MDW2:44 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
4h 54m
1 stop
PNS11:39 amPensacola
$354
Find similar
Delta
Dec 31
PNS5:31 pmPensacola
4h 51m
1 stop
MDW10:22 pmChicago Midway
Jan 5
MDW6:45 amChicago Midway
4h 54m
1 stop
PNS11:39 amPensacola
$399
Find similar

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Feb 17
PNS7:05 amPensacola
5h 55m
1 stop
MDW1:00 pmChicago Midway
Feb 22
MDW5:25 amChicago Midway
4h 25m
1 stop
PNS9:50 amPensacola
$249
Find similar
Southwest
Jan 25
PNS4:25 pmPensacola
3h 45m
1 stop
MDW8:10 pmChicago Midway
Feb 14
MDW9:20 amChicago Midway
6h 45m
1 stop
PNS4:05 pmPensacola
$255
Find similar
Southwest
Apr 11
PNS9:40 amPensacola
4h 50m
1 stop
MDW2:30 pmChicago Midway
Apr 18
MDW7:25 amChicago Midway
8h 50m
2 stops
PNS4:15 pmPensacola
$274
Find similar

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 December 18, 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

Tue 2/17

5:59 pm-7:07 pm

2 stops25h 08m

Chicago Midway

Sun 2/22

7:30 am-5:42 pm

1 stop10h 12m

$210

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

5:54 pm-10:07 pm

1 stop4h 13m

Chicago Midway

Mon 1/19

6:00 am-12:35 pm

1 stop6h 35m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

5:33 pm-7:27 am

2 stops13h 54m

Chicago Midway

Mon 1/19

10:07 am-4:37 pm

1 stop6h 30m

$240

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 1/25

5:33 pm-7:58 pm

1 stop26h 25m

Chicago Midway

Sat 2/14

9:15 am-7:35 am

2 stops22h 20m

$246

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 2/17

7:05 am-1:00 pm

1 stop5h 55m

Chicago Midway

Sun 2/22

5:25 am-9:50 am

1 stop4h 25m

$249

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 1/25

4:25 pm-8:10 pm

1 stop3h 45m

Chicago Midway

Sat 2/14

9:20 am-4:05 pm

1 stop6h 45m

$255

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 4/11

9:40 am-2:30 pm

1 stop4h 50m

Chicago Midway

Sat 4/18

7:25 am-4:15 pm

2 stops8h 50m

$274

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 4/11

11:15 am-9:05 pm

2 stops9h 50m

Chicago Midway

Sat 4/18

10:30 am-5:20 pm

2 stops6h 50m

$314

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 4/11

9:40 am-2:30 pm

1 stop4h 50m

Chicago Midway

Sat 4/18

8:10 am-10:25 am

Nonstop2h 15m

$343

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 1/25

7:05 am-5:35 pm

2 stops10h 30m

Chicago Midway

Sat 2/14

5:00 am-4:05 pm

2 stops11h 05m

$346

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 $676.

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 is only 1 cabin class 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

Fastest flight time

2h 15m

Direct flights

Mon, Tue and Sun
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 15m
Direct flights go from Pensacola to Chicago Midway Airport on Monday, Tuesday and Sunday. There are no airlines offering direct flights.
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 2h 15m, 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
DeltaPriceFrom $201Free CancellationRating
7.9
8,005 reviews
Search Delta flights
SouthwestPriceFrom $216Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

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
Valparaiso
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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