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Cheap flights from Pensacola to Chicago from $68

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 5/2. 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
7:00 am - 5:44 pm
PNS
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
9:51 pm - 9:14 pm
MDW
-
PNS
23h 23m
1 stop
$209Multiple Airlines
Thu, Mar 19 - Mon, Mar 23
Southwest Logo
5:20 pm - 11:30 pm
PNS
-
MDW
6h 10m
1 stop
Southwest Logo
8:25 am - 10:40 am
MDW
-
PNS
2h 15mnonstop
$217Southwest
Thu, Apr 23 - Sun, Apr 26
Multiple Airlines Logo
6:37 pm - 10:29 pm
PNS
-
MDW
27h 52m
2 stops
Multiple Airlines Logo
9:51 pm - 9:14 pm
MDW
-
PNS
23h 23m
1 stop
$219Multiple Airlines
Sun, Mar 1 - Mon, Mar 16
Multiple Airlines Logo
6:37 pm - 1:08 pm
PNS
-
MDW
18h 31m
1 stop
Multiple Airlines Logo
8:00 am - 5:42 pm
MDW
-
PNS
9h 42m
1 stop
$221Multiple Airlines
Fri, Mar 6 - Sun, Mar 8
Delta Logo
6:00 am - 9:54 am
PNS
-
MDW
3h 54m
1 stop
Delta Logo
6:00 am - 10:06 am
MDW
-
PNS
4h 06m
1 stop
$227Delta
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
7:20 am - 1:30 pm
PNS
-
MDW
6h 10m
1 stop
Southwest Logo
5:40 am - 9:40 am
MDW
-
PNS
4h 00m
1 stop
$228Southwest
Fri, Feb 27 - Sat, Feb 28
Southwest Logo
1:10 pm - 8:55 pm
PNS
-
MDW
7h 45m
2 stops
Southwest Logo
9:20 am - 4:05 pm
MDW
-
PNS
6h 45m
1 stop
$233Southwest
Fri, Feb 27 - Sat, Feb 28
Delta Logo
6:00 am - 9:54 am
PNS
-
MDW
3h 54m
1 stop
Delta Logo
10:45 am - 3:09 pm
MDW
-
PNS
4h 24m
1 stop
$237Delta
Thu, Mar 5 - Tue, Mar 10
Multiple Airlines Logo
7:00 am - 5:44 pm
PNS
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
9:51 pm - 1:16 pm
MDW
-
PNS
15h 25m
2 stops
$239Multiple Airlines
Thu, Mar 19 - Mon, Mar 23
Multiple Airlines Logo
6:37 pm - 7:07 pm
PNS
-
MDW
24h 30m
2 stops
Multiple Airlines Logo
7:30 am - 5:42 pm
MDW
-
PNS
10h 12m
1 stop
$242Multiple Airlines
Mon, Feb 23 - Thu, Feb 26

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Mar 5
PNS6:00 amPensacola
3h 54m
1 stop
MDW9:54 amChicago Midway
Mar 10
MDW6:00 amChicago Midway
4h 06m
1 stop
PNS10:06 amPensacola
$227
Delta
Mar 5
PNS6:00 amPensacola
3h 54m
1 stop
MDW9:54 amChicago Midway
Mar 10
MDW10:45 amChicago Midway
4h 24m
1 stop
PNS3:09 pmPensacola
$237
Delta
Feb 26
PNS6:01 pmPensacola
4h 30m
1 stop
MDW10:31 pmChicago Midway
Mar 1
MDW6:00 amChicago Midway
6h 30m
1 stop
PNS12:30 pmPensacola
$247

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Apr 23
PNS5:20 pmPensacola
6h 10m
1 stop
MDW11:30 pmChicago Midway
Apr 26
MDW8:25 amChicago Midway
2h 15m
PNS10:40 amPensacola
$217
Southwest
Feb 27
PNS7:20 amPensacola
6h 10m
1 stop
MDW1:30 pmChicago Midway
Feb 28
MDW5:40 amChicago Midway
4h 00m
1 stop
PNS9:40 amPensacola
$228
Southwest
Feb 27
PNS1:10 pmPensacola
7h 45m
2 stops
MDW8:55 pmChicago Midway
Feb 28
MDW9:20 amChicago Midway
6h 45m
1 stop
PNS4:05 pmPensacola
$233

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 February 10, 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

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/19

7:00 am-5:44 pm

1 stop10h 44m

Chicago Midway

Mon 3/23

9:51 pm-9:14 pm

1 stop23h 23m

$209

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/23

5:20 pm-11:30 pm

1 stop6h 10m

Chicago Midway

Sun 4/26

8:25 am-10:40 am

Nonstop2h 15m

$217

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 3/1

6:37 pm-10:29 pm

2 stops27h 52m

Chicago Midway

Mon 3/16

9:51 pm-9:14 pm

1 stop23h 23m

$219

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 3/6

6:37 pm-1:08 pm

1 stop18h 31m

Chicago Midway

Sun 3/8

8:00 am-5:42 pm

1 stop9h 42m

$221

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Tue 3/10

6:00 am-10:06 am

1 stop4h 06m

$227

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 2/27

7:20 am-1:30 pm

1 stop6h 10m

Chicago Midway

Sat 2/28

5:40 am-9:40 am

1 stop4h 00m

$228

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 2/27

1:10 pm-8:55 pm

2 stops7h 45m

Chicago Midway

Sat 2/28

9:20 am-4:05 pm

1 stop6h 45m

$233

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Tue 3/10

10:45 am-3:09 pm

1 stop4h 24m

$237

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/19

7:00 am-5:44 pm

1 stop10h 44m

Chicago Midway

Mon 3/23

9:51 pm-1:16 pm

2 stops15h 25m

$239

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 2/23

6:37 pm-7:07 pm

2 stops24h 30m

Chicago Midway

Thu 2/26

7:30 am-5:42 pm

1 stop10h 12m

$242

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 $313. 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, Tuesday 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 $472.

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 $337 when looking at flights departing at noon. 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

Best Price Found

$429

Fastest flight time

2h 15m

Direct flights

Mon, Thu, Fri, Sat and Sun
The best flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $429
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 15m
Direct flights go from Pensacola to Chicago Midway Airport on Monday, Thursday, Friday, Saturday 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
SouthwestPriceFrom $216Free CancellationRating
8.0
4,282 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,178 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 2 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 $296. 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
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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