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Cheap flights from Pensacola to Chicago from $76

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 5/17. 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
1 adult, Economy, 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
4:31 pm - 7:59 am
PNS
-
MDW
15h 28m
1 stop
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
$193Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
6:36 am - 7:31 pm
PNS
-
MDW
12h 55m
2 stops
Multiple Airlines Logo
9:14 am - 9:38 pm
MDW
-
PNS
12h 24m
1 stop
$212Multiple Airlines
Thu, Apr 30 - Sat, May 2
Multiple Airlines Logo
6:36 am - 10:19 pm
PNS
-
MDW
15h 43m
2 stops
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
$213Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
6:36 am - 10:26 pm
PNS
-
MDW
15h 50m
2 stops
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
$228Multiple Airlines
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
3:36 pm - 9:21 pm
PNS
-
MDW
5h 45m
1 stop
Frontier Logo
5:05 am - 2:51 pm
MDW
-
PNS
9h 46m
1 stop
$235Frontier
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
6:36 am - 3:57 pm
PNS
-
MDW
9h 21m
1 stop
Multiple Airlines Logo
6:00 am - 7:23 pm
MDW
-
PNS
13h 23m
2 stops
$237Multiple Airlines
Fri, May 8 - Mon, May 11
Multiple Airlines Logo
7:38 pm - 3:57 pm
PNS
-
MDW
20h 19m
1 stop
Multiple Airlines Logo
6:00 am - 5:03 pm
MDW
-
PNS
11h 03m
2 stops
$242Multiple Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
4:31 pm - 7:31 pm
PNS
-
MDW
27h 00m
2 stops
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
$243Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Multiple Airlines Logo
6:36 am - 7:31 pm
PNS
-
MDW
12h 55m
2 stops
Multiple Airlines Logo
8:39 am - 3:36 pm
MDW
-
PNS
6h 57m
1 stop
$244Multiple Airlines
Fri, May 1 - Sun, May 3
Multiple Airlines Logo
6:36 am - 10:22 pm
PNS
-
MDW
15h 46m
2 stops
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
$253Multiple Airlines
Thu, Apr 23 - Mon, Apr 27

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Apr 30
PNS5:20 pmPensacola
6h 10m
1 stop
MDW11:30 pmChicago Midway
May 2
MDW8:10 amChicago Midway
2h 15m
PNS10:25 amPensacola
$281
Southwest
Apr 28
PNS7:40 amPensacola
7h 15m
2 stops
MDW2:55 pmChicago Midway
Apr 29
MDW3:00 pmChicago Midway
4h 00m
1 stop
PNS7:00 pmPensacola
$296
Southwest
Apr 16
PNS1:15 pmPensacola
8h 00m
2 stops
MDW9:15 pmChicago Midway
Apr 20
MDW7:50 amChicago Midway
7h 50m
2 stops
PNS3:40 pmPensacola
$301

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Apr 23
PNS5:26 pmPensacola
5h 02m
1 stop
MDW10:28 pmChicago Midway
Apr 29
MDW6:00 amChicago Midway
5h 53m
1 stop
PNS11:53 amPensacola
$291
Delta
Apr 20
PNS5:26 pmPensacola
5h 02m
1 stop
MDW10:28 pmChicago Midway
Apr 27
MDW6:00 amChicago Midway
5h 55m
1 stop
PNS11:55 amPensacola
$315
Delta
Apr 20
PNS5:26 pmPensacola
5h 02m
1 stop
MDW10:28 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
4h 02m
1 stop
PNS10:02 amPensacola
$332

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 March 27, 2026.
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

Cheapest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/16

4:31 pm-7:59 am

1 stop15h 28m

Chicago Midway

Mon 4/20

9:14 am-3:36 pm

1 stop6h 22m

$193

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/30

6:36 am-7:31 pm

2 stops12h 55m

Chicago Midway

Sat 5/2

9:14 am-9:38 pm

1 stop12h 24m

$212

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/16

6:36 am-10:19 pm

2 stops15h 43m

Chicago Midway

Mon 4/20

9:14 am-3:36 pm

1 stop6h 22m

$213

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 4/17

6:36 am-10:26 pm

2 stops15h 50m

Chicago Midway

Mon 4/20

9:14 am-3:36 pm

1 stop6h 22m

$228
Quickest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/9

3:36 pm-9:21 pm

1 stop5h 45m

Chicago Midway

Sun 4/12

5:05 am-2:51 pm

1 stop9h 46m

$235

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 5/8

6:36 am-3:57 pm

1 stop9h 21m

Chicago Midway

Mon 5/11

6:00 am-7:23 pm

2 stops13h 23m

$237

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 5/7

7:38 pm-3:57 pm

1 stop20h 19m

Chicago Midway

Mon 5/11

6:00 am-5:03 pm

2 stops11h 03m

$242

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 4/20

4:31 pm-7:31 pm

2 stops27h 00m

Chicago Midway

Mon 4/27

9:14 am-3:36 pm

1 stop6h 22m

$243

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 5/1

6:36 am-7:31 pm

2 stops12h 55m

Chicago Midway

Sun 5/3

8:39 am-3:36 pm

1 stop6h 57m

$244

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/23

6:36 am-10:22 pm

2 stops15h 46m

Chicago Midway

Mon 4/27

9:14 am-3:36 pm

1 stop6h 22m

$253

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, Friday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Friday departure recently was $297. 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 $429.

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

Flying to Chicago Midway Airport from Pensacola at noon is the least expensive time of day to depart. momondo users have found prices as low as $327 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $366. 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

Best Price Found

$158

Fastest flight time

2h 15m

Direct flights

Mon, Wed, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $158. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $282.
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 15m
Direct flights go from Pensacola to Chicago Midway Airport on Monday, Wednesday, Friday, Saturday and 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 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
SouthwestPriceFrom $222Free CancellationRating
8.0
4,331 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,340 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 8 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago Midway Airport starts from $222 round-trip, up to an average price of $307. 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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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