Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Pensacola from $104

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Pensacola departing on 12/9. 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

Discover deals from 900+ travel sites with momondo.

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 Chicago Midway Airport to Pensacola (MDW-PNS)

Cheap round-trip flights

Delta Logo
10:35 am - 2:26 pmMDW-PNS
3h 51m1 stop
Delta Logo
9:25 am - 4:25 pmPNS-MDW
7h 00m1 stop
$217Delta
Find Deal
Tue, Jan 20 - Wed, Jan 28
Delta Logo
6:00 am - 10:49 amMDW-PNS
4h 49m1 stop
Delta Logo
6:00 am - 9:56 amPNS-MDW
3h 56m1 stop
$223Delta
Find Deal
Tue, Jan 20 - Sat, Jan 24
Delta Logo
6:00 am - 10:49 amMDW-PNS
4h 49m1 stop
Delta Logo
6:00 am - 12:01 pmPNS-MDW
6h 01m1 stop
$229Delta
Find Deal
Sat, Jan 17 - Fri, Jan 30
Delta Logo
6:00 am - 10:50 amMDW-PNS
4h 50m1 stop
Delta Logo
7:00 am - 11:48 amPNS-MDW
4h 48m1 stop
$233Delta
Find Deal
Fri, Sep 12 - Tue, Sep 16
Southwest Logo
10:15 am - 2:35 pmMDW-PNS
4h 20m1 stop
Southwest Logo
7:35 am - 3:00 pmPNS-MDW
7h 25m2 stops
$238Southwest
Find Deal
Fri, Sep 12 - Tue, Sep 16
Delta Logo
4:31 pm - 9:43 pmMDW-PNS
5h 12m1 stop
Delta Logo
2:13 pm - 9:10 pmPNS-MDW
6h 57m1 stop
$239Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Southwest Logo
8:20 am - 10:30 amMDW-PNS
2h 10mnonstop
Southwest Logo
7:35 am - 3:00 pmPNS-MDW
7h 25m2 stops
$244Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Logo
9:48 am - 6:10 pmMDW-PNS
8h 22m1 stop
Logo
7:10 pm - 7:23 amPNS-MDW
12h 13m1 stop
$261
Find Deal
Fri, Sep 26 - Sun, Sep 28
Frontier Logo
4:48 pm - 4:26 pmMDW-PNS
23h 38m1 stop
Frontier Logo
5:21 pm - 3:53 pmPNS-MDW
22h 32m1 stop
$281Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
Logo
8:05 am - 5:01 pmMDW-PNS
8h 56m2 stops
Logo
6:25 pm - 10:21 amPNS-MDW
15h 56m1 stop
$327
Find Deal
Tue, Oct 14 - Fri, Oct 17

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Jan 20
MDW10:35 amChicago Midway
3h 51m
1 stop
PNS2:26 pmPensacola
Jan 28
PNS9:25 amPensacola
7h 00m
1 stop
MDW4:25 pmChicago Midway
$217
Find similar
Delta
Jan 20
MDW6:00 amChicago Midway
4h 49m
1 stop
PNS10:49 amPensacola
Jan 24
PNS6:00 amPensacola
3h 56m
1 stop
MDW9:56 amChicago Midway
$223
Find similar
Delta
Jan 17
MDW6:00 amChicago Midway
4h 49m
1 stop
PNS10:49 amPensacola
Jan 30
PNS6:00 amPensacola
6h 01m
1 stop
MDW12:01 pmChicago Midway
$229
Find similar

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Sep 12
MDW10:15 amChicago Midway
4h 20m
1 stop
PNS2:35 pmPensacola
Sep 16
PNS7:35 amPensacola
7h 25m
2 stops
MDW3:00 pmChicago Midway
$238
Find similar
Southwest
Sep 10
MDW9:00 amChicago Midway
6h 35m
1 stop
PNS3:35 pmPensacola
Sep 15
PNS3:20 pmPensacola
5h 30m
1 stop
MDW8:50 pmChicago Midway
$239
Find similar
Southwest
Sep 13
MDW8:20 amChicago Midway
2h 10m
PNS10:30 amPensacola
Sep 16
PNS7:35 amPensacola
7h 25m
2 stops
MDW3:00 pmChicago Midway
$244
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Pensacola 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 August 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 1/20

10:35 am-2:26 pm

1 stop3h 51m

Pensacola

Wed 1/28

9:25 am-4:25 pm

1 stop7h 00m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 1/20

6:00 am-10:49 am

1 stop4h 49m

Pensacola

Sat 1/24

6:00 am-9:56 am

1 stop3h 56m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 1/17

6:00 am-10:49 am

1 stop4h 49m

Pensacola

Fri 1/30

6:00 am-12:01 pm

1 stop6h 01m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 9/12

6:00 am-10:50 am

1 stop4h 50m

Pensacola

Tue 9/16

7:00 am-11:48 am

1 stop4h 48m

$233

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 9/12

10:15 am-2:35 pm

1 stop4h 20m

Pensacola

Tue 9/16

7:35 am-3:00 pm

2 stops7h 25m

$238

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/13

4:31 pm-9:43 pm

1 stop5h 12m

Pensacola

Sat 9/20

2:13 pm-9:10 pm

1 stop6h 57m

$239

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/13

8:20 am-10:30 am

Nonstop2h 10m

Pensacola

Tue 9/16

7:35 am-3:00 pm

2 stops7h 25m

$244

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 9/26

9:48 am-6:10 pm

1 stop8h 22m

Pensacola

Sun 9/28

7:10 pm-7:23 am

1 stop12h 13m

$261

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 9/12

4:48 pm-4:26 pm

1 stop23h 38m

Pensacola

Sun 9/14

5:21 pm-3:53 pm

1 stop22h 32m

$281

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 10/14

8:05 am-5:01 pm

2 stops8h 56m

Pensacola

Fri 10/17

6:25 pm-10:21 am

1 stop15h 56m

$327

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Pensacola from

How to get the cheapest flight ticket from Chicago Midway Airport to Pensacola

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 month to fly to Pensacola?

The cheapest month to fly to Pensacola from Chicago Midway Airport is in January. Flight prices, which tend to average around $228, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago Midway Airport during September instead. Flights to Pensacola in September, while not as cheap as those in January, still average around $241.

What is the cheapest day to depart on your flight to Pensacola?

On average, the least expensive day to fly to Pensacola from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $317. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $438.

What is the cheapest time of day to depart on your flight to Pensacola?

The cheapest time of day to fly to Pensacola is in the afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $395. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Pensacola flight route?

Fly from Chicago Midway to Pensacola for the best Chicago Midway - Pensacola flight prices

What cabin class options are available on Chicago Midway to Pensacola flights?

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

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Pensacola.

When to book flights from Chicago Midway Airport to Pensacola

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Pensacola according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Pensacola (MDW to PNS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Pensacola

Best Price Found

$268

Fastest flight time

2h 10m

Direct flights

Sun

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago Midway Airport in the past 72 hours is $268. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $317.
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
Direct flights go from Chicago Midway Airport to Pensacola on Sunday. The only airline offering direct flights is Southwest.
There is 1 airport near Pensacola: Pensacola (PNS)
Search flight deals

  • How far is Chicago Midway to Pensacola by plane?

    Chicago Midway and Pensacola are 785.3 mi apart from one another. A reasonable flight in good conditions will take 2h 10m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Pensacola Airport?

    Prices for flights from Chicago Midway Airport to Pensacola Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Pensacola Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola Airport.

  • What documentation or ID do you need to fly to Pensacola Airport?

    The necessary travel and health documents for your Pensacola Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Pensacola?

  • What is the most popular airline from Chicago Midway Airport to Pensacola?

Best airlines flying from Chicago Midway Airport to Pensacola

Compare and see reviews for airlines that fly from Chicago Midway Airport to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
7.9
7,977 reviews
Search Delta flights
SouthwestPriceFrom $216Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Perdido Key
Navarre Beach
Navarre
Atmore
Milton
Gulf Breeze
Warrington
Evergreen

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Pensacola?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pensacola for you.

Can I find flights from Chicago to Pensacola with flexible booking policies on momondo?

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Pensacola?

Once all potential Chicago to Pensacola flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Pensacola right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Pensacola 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
Tue 9/2
Tue 9/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States