Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Pensacola to Chicago from $133

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 8/18. 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

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

Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
$349Southwest
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
$352Southwest
Wed, Jun 24 - Sat, Jun 27
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
8:45 am - 10:55 am
MDW
-
PNS
2h 10mnonstop
$353Southwest
Wed, Jun 24 - Sun, Jun 28
Southwest Logo
12:50 pm - 3:05 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
$355Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
10:40 am - 12:55 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
$356Southwest
Thu, Jun 25 - Sat, Jun 27
Southwest Logo
4:20 pm - 11:40 pm
PNS
-
MDW
7h 20m
1 stop
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
$358Southwest
Fri, May 29 - Sat, May 30
Southwest Logo
5:30 pm - 11:10 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
$359Southwest
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
10:00 am - 2:55 pm
PNS
-
MDW
4h 55m
1 stop
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
$361Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
5:30 pm - 11:10 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
$362Southwest
Wed, Jun 24 - Sat, Jun 27
Southwest Logo
5:30 pm - 9:10 pm
PNS
-
MDW
3h 40m
1 stop
Southwest Logo
8:45 am - 10:55 am
MDW
-
PNS
2h 10mnonstop
$363Southwest
Wed, Jun 24 - Sun, Jun 28

Delta flights from Pensacola to Chicago Midway Airport

Our best Delta deals on Pensacola to Chicago Midway Airport flight tickets
Delta
Jun 30
PNS9:23 amPensacola
6h 17m
1 stop
MDW3:40 pmChicago Midway
Jul 7
MDW11:05 amChicago Midway
5h 58m
1 stop
PNS5:03 pmPensacola
$369
Delta
Aug 15
PNS9:22 amPensacola
6h 16m
1 stop
MDW3:38 pmChicago Midway
Aug 18
MDW12:46 pmChicago Midway
6h 34m
1 stop
PNS7:20 pmPensacola
$372
Delta
Jun 23
PNS6:11 pmPensacola
4h 06m
1 stop
MDW10:17 pmChicago Midway
Jun 28
MDW6:00 amChicago Midway
4h 52m
1 stop
PNS10:52 amPensacola
$373

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Jun 16
PNS3:45 pmPensacola
2h 15m
MDW6:00 pmChicago Midway
Jun 23
MDW12:55 pmChicago Midway
2h 10m
PNS3:05 pmPensacola
$349
Southwest
Jun 24
PNS3:45 pmPensacola
2h 15m
MDW6:00 pmChicago Midway
Jun 27
MDW9:00 amChicago Midway
2h 10m
PNS11:10 amPensacola
$352
Southwest
Jun 24
PNS3:45 pmPensacola
2h 15m
MDW6:00 pmChicago Midway
Jun 28
MDW8:45 amChicago Midway
2h 10m
PNS10:55 amPensacola
$353

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 May 20, 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 6/16

3:45 pm-6:00 pm

Nonstop2h 15m

Chicago Midway

Tue 6/23

12:55 pm-3:05 pm

Nonstop2h 10m

$349

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/24

3:45 pm-6:00 pm

Nonstop2h 15m

Chicago Midway

Sat 6/27

9:00 am-11:10 am

Nonstop2h 10m

$352

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/24

3:45 pm-6:00 pm

Nonstop2h 15m

Chicago Midway

Sun 6/28

8:45 am-10:55 am

Nonstop2h 10m

$353

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 7/4

12:50 pm-3:05 pm

Nonstop2h 15m

Chicago Midway

Sat 7/11

9:00 am-11:10 am

Nonstop2h 10m

$355

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 6/25

10:40 am-12:55 pm

Nonstop2h 15m

Chicago Midway

Sat 6/27

9:00 am-11:10 am

Nonstop2h 10m

$356

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 5/29

4:20 pm-11:40 pm

1 stop7h 20m

Chicago Midway

Sat 5/30

8:10 am-10:25 am

Nonstop2h 15m

$358

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 6/16

5:30 pm-11:10 pm

1 stop5h 40m

Chicago Midway

Tue 6/23

12:55 pm-3:05 pm

Nonstop2h 10m

$359

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 7/4

10:00 am-2:55 pm

1 stop4h 55m

Chicago Midway

Sat 7/11

9:00 am-11:10 am

Nonstop2h 10m

$361

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/24

5:30 pm-11:10 pm

1 stop5h 40m

Chicago Midway

Sat 6/27

9:00 am-11:10 am

Nonstop2h 10m

$362

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/24

5:30 pm-9:10 pm

1 stop3h 40m

Chicago Midway

Sun 6/28

8:45 am-10:55 am

Nonstop2h 10m

$363

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, Friday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Friday departure recently was $319. 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 $466.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $429. 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?

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

$218

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 $218. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $398.
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
SouthwestPriceFrom $228Free CancellationRating
7.9
4,284 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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.

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 6/19
Fri 6/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago