Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pensacola to Chicago from $123

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 9/5. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:20 pm - 10:20 pm
PNS
-
MDW
6h 00m
1 stop
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$241Southwest
Tue, Aug 25 - Wed, Aug 26
Delta Logo
4:28 pm - 10:36 pm
PNS
-
MDW
6h 08m
1 stop
Delta Logo
5:10 pm - 11:44 pm
MDW
-
PNS
6h 34m
1 stop
$245Delta
Sat, Aug 15 - Mon, Aug 17
Southwest Logo
7:00 am - 3:30 pm
PNS
-
MDW
8h 30m
2 stops
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$246Southwest
Tue, Aug 25 - Wed, Aug 26
Southwest Logo
10:20 am - 4:55 pm
PNS
-
MDW
6h 35m
1 stop
Southwest Logo
6:45 am - 4:15 pm
MDW
-
PNS
9h 30m
2 stops
$251Southwest
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
7:55 am - 3:25 pm
PNS
-
MDW
7h 30m
2 stops
Southwest Logo
9:55 am - 4:15 pm
MDW
-
PNS
6h 20m
2 stops
$256Southwest
Tue, Aug 25 - Sat, Aug 29
Delta Logo
5:52 pm - 10:45 pm
PNS
-
MDW
4h 53m
1 stop
Delta Logo
6:05 am - 12:39 pm
MDW
-
PNS
6h 34m
1 stop
$273Delta
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
4:20 pm - 10:20 pm
PNS
-
MDW
6h 00m
1 stop
Southwest Logo
5:00 am - 1:05 pm
MDW
-
PNS
8h 05m
2 stops
$288Southwest
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
4:20 pm - 10:20 pm
PNS
-
MDW
6h 00m
1 stop
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$306Southwest
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
3:00 pm - 8:40 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
7:55 am - 12:10 pm
MDW
-
PNS
4h 15m
1 stop
$310Southwest
Tue, Aug 25 - Fri, Aug 28
Southwest Logo
3:00 pm - 8:40 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
5:30 am - 1:05 pm
MDW
-
PNS
7h 35m
2 stops
$316Southwest
Tue, Aug 25 - Fri, Aug 28

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Aug 15
PNS4:28 pmPensacola
6h 08m
1 stop
MDW10:36 pmChicago Midway
Aug 17
MDW5:10 pmChicago Midway
6h 34m
1 stop
PNS11:44 pmPensacola
$245
Delta
Sep 18
PNS5:52 pmPensacola
4h 53m
1 stop
MDW10:45 pmChicago Midway
Sep 21
MDW6:05 amChicago Midway
6h 34m
1 stop
PNS12:39 pmPensacola
$273
Delta
Aug 25
PNS7:00 amPensacola
4h 51m
1 stop
MDW11:51 amChicago Midway
Aug 29
MDW6:11 amChicago Midway
6h 39m
1 stop
PNS12:50 pmPensacola
$333

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Aug 25
PNS4:20 pmPensacola
6h 00m
1 stop
MDW10:20 pmChicago Midway
Aug 26
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
$241
Southwest
Aug 25
PNS7:00 amPensacola
8h 30m
2 stops
MDW3:30 pmChicago Midway
Aug 26
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
$246
Southwest
Aug 25
PNS10:20 amPensacola
6h 35m
1 stop
MDW4:55 pmChicago Midway
Aug 29
MDW6:45 amChicago Midway
9h 30m
2 stops
PNS4:15 pmPensacola
$251

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 8, 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
Quickest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

4:20 pm-10:20 pm

1 stop6h 00m

Chicago Midway

Wed 8/26

2:00 pm-5:35 pm

1 stop3h 35m

$241

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 8/15

4:28 pm-10:36 pm

1 stop6h 08m

Chicago Midway

Mon 8/17

5:10 pm-11:44 pm

1 stop6h 34m

$245

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

7:00 am-3:30 pm

2 stops8h 30m

Chicago Midway

Wed 8/26

2:00 pm-5:35 pm

1 stop3h 35m

$246

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

10:20 am-4:55 pm

1 stop6h 35m

Chicago Midway

Sat 8/29

6:45 am-4:15 pm

2 stops9h 30m

$251

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

7:55 am-3:25 pm

2 stops7h 30m

Chicago Midway

Sat 8/29

9:55 am-4:15 pm

2 stops6h 20m

$256

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 9/18

5:52 pm-10:45 pm

1 stop4h 53m

Chicago Midway

Mon 9/21

6:05 am-12:39 pm

1 stop6h 34m

$273

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 9/21

4:20 pm-10:20 pm

1 stop6h 00m

Chicago Midway

Mon 9/28

5:00 am-1:05 pm

2 stops8h 05m

$288

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 9/4

4:20 pm-10:20 pm

1 stop6h 00m

Chicago Midway

Tue 9/8

2:00 pm-5:35 pm

1 stop3h 35m

$306

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

3:00 pm-8:40 pm

1 stop5h 40m

Chicago Midway

Fri 8/28

7:55 am-12:10 pm

1 stop4h 15m

$310

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/25

3:00 pm-8:40 pm

1 stop5h 40m

Chicago Midway

Fri 8/28

5:30 am-1:05 pm

2 stops7h 35m

$316

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Pensacola and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Pensacola, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Pensacola during the month February is also very affordable. Most momondo users find prices during this month for around $0.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Saturday departure recently was $400. 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, Monday 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 $567.

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 $429 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $447. 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 Airport flights?

There is only 1 cabin class available to choose from on Pensacola to Chicago Midway Airport 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?

You could potentially save up to 14% on your flight if you consider stops on a Pensacola to Chicago Midway Airport flight.

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

$211

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $211. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $413.
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 15m
Direct flights go from Pensacola to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Pensacola to Chicago Midway Airport

  • 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 $228Free CancellationRating
7.8
8,451 reviews
Search Delta flights
SouthwestPriceFrom $237Free CancellationRating
7.9
4,250 reviews
Search Southwest 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 5 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago Midway Airport starts from $237 round-trip, up to an average price of $397. Our users have rated Southwest at 7.9/10.

Traveling to a place near Chicago?

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 8/7
Fri 8/14
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago