Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Pensacola from $70

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 1/27. 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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:40 am - 5:05 pmMDW-PNS
10h 25m2 stops
Southwest Logo
7:45 am - 4:55 pmPNS-MDW
9h 10m2 stops
$220Southwest
Find Deal
Sat, Jan 31 - Sat, Feb 7
Southwest Logo
6:00 am - 9:50 amMDW-PNS
3h 50m1 stop
Southwest Logo
5:45 pm - 9:40 pmPNS-MDW
3h 55m1 stop
$222Southwest
Find Deal
Sat, Feb 7 - Fri, Feb 13
Multiple Airlines Logo
6:15 pm - 4:55 pmMDW-PNS
22h 40m1 stop
Multiple Airlines Logo
4:51 pm - 9:43 pmPNS-MDW
28h 52m2 stops
$223Multiple Airlines
Find Deal
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
12:30 pm - 6:50 pmMDW-PNS
6h 20m2 stops
Southwest Logo
7:50 am - 2:55 pmPNS-MDW
7h 05m2 stops
$224Southwest
Find Deal
Fri, Feb 6 - Wed, Feb 11
Southwest Logo
6:00 am - 9:50 amMDW-PNS
3h 50m1 stop
Southwest Logo
1:10 pm - 8:55 pmPNS-MDW
7h 45m2 stops
$227Southwest
Find Deal
Sat, Feb 7 - Fri, Feb 13
Southwest Logo
6:15 am - 3:15 pmMDW-PNS
9h 00m2 stops
Southwest Logo
4:25 pm - 10:30 pmPNS-MDW
6h 05m1 stop
$228Southwest
Find Deal
Wed, Jan 7 - Sun, Jan 11
Delta Logo
12:46 pm - 6:42 pmMDW-PNS
5h 56m1 stop
Delta Logo
1:37 pm - 5:45 pmPNS-MDW
4h 08m1 stop
$229Delta
Find Deal
Wed, Feb 18 - Mon, Feb 23
Delta Logo
6:00 am - 1:05 pmMDW-PNS
7h 05m1 stop
Delta Logo
5:00 pm - 10:42 pmPNS-MDW
5h 42m1 stop
$230Delta
Find Deal
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:00 am - 9:50 amMDW-PNS
3h 50m1 stop
Southwest Logo
7:50 am - 6:50 pmPNS-MDW
11h 00m2 stops
$237Southwest
Find Deal
Fri, Jan 9 - Mon, Jan 12
Delta Logo
6:45 am - 11:39 amMDW-PNS
4h 54m1 stop
Delta Logo
1:40 pm - 5:29 pmPNS-MDW
3h 49m1 stop
$238Delta
Find Deal
Sat, Jan 10 - Tue, Jan 20

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Apr 11
MDW4:30 pmChicago Midway
6h 37m
1 stop
PNS11:07 pmPensacola
Apr 18
PNS3:35 pmPensacola
6h 10m
1 stop
MDW9:45 pmChicago Midway
$229
Find similar
Delta
Jan 10
MDW6:45 amChicago Midway
4h 54m
1 stop
PNS11:39 amPensacola
Jan 20
PNS1:40 pmPensacola
3h 49m
1 stop
MDW5:29 pmChicago Midway
$238
Find similar
Delta
Jan 1
MDW6:00 amChicago Midway
4h 20m
1 stop
PNS10:20 amPensacola
Jan 8
PNS5:54 pmPensacola
4h 13m
1 stop
MDW10:07 pmChicago Midway
$248
Find similar

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Jan 31
MDW6:40 amChicago Midway
10h 25m
2 stops
PNS5:05 pmPensacola
Feb 7
PNS7:45 amPensacola
9h 10m
2 stops
MDW4:55 pmChicago Midway
$220
Find similar
Southwest
Feb 7
MDW6:00 amChicago Midway
3h 50m
1 stop
PNS9:50 amPensacola
Feb 13
PNS5:45 pmPensacola
3h 55m
1 stop
MDW9:40 pmChicago Midway
$222
Find similar
Southwest
Feb 6
MDW12:30 pmChicago Midway
6h 20m
2 stops
PNS6:50 pmPensacola
Feb 11
PNS7:50 amPensacola
7h 05m
2 stops
MDW2:55 pmChicago Midway
$224
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 December 3, 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

Sat 1/31

6:40 am-5:05 pm

2 stops10h 25m

Pensacola

Sat 2/7

7:45 am-4:55 pm

2 stops9h 10m

$220

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/7

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Fri 2/13

5:45 pm-9:40 pm

1 stop3h 55m

$222

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/14

6:15 pm-4:55 pm

1 stop22h 40m

Pensacola

Sat 2/21

4:51 pm-9:43 pm

2 stops28h 52m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/6

12:30 pm-6:50 pm

2 stops6h 20m

Pensacola

Wed 2/11

7:50 am-2:55 pm

2 stops7h 05m

$224

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/7

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Fri 2/13

1:10 pm-8:55 pm

2 stops7h 45m

$227

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 1/7

6:15 am-3:15 pm

2 stops9h 00m

Pensacola

Sun 1/11

4:25 pm-10:30 pm

1 stop6h 05m

$228

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

12:46 pm-6:42 pm

1 stop5h 56m

Pensacola

Mon 2/23

1:37 pm-5:45 pm

1 stop4h 08m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/14

6:00 am-1:05 pm

1 stop7h 05m

Pensacola

Sat 2/21

5:00 pm-10:42 pm

1 stop5h 42m

$230

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/9

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Mon 1/12

7:50 am-6:50 pm

2 stops11h 00m

$237

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 1/10

6:45 am-11:39 am

1 stop4h 54m

Pensacola

Tue 1/20

1:40 pm-5:29 pm

1 stop3h 49m

$238

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 September. Flight prices, which tend to average around $217, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Pensacola from Chicago Midway Airport during January instead. Flights to Pensacola in January, while not as cheap as those in September, still average around $245.

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 $315. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Saturday 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 $390.

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

The cheapest time of day to fly to Pensacola is at noon when flights can be purchased for as low as $323. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $787. Departure times in the afternoon 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

Fastest flight time

2h 10m

Direct flights

Mon, Wed, Thu, Sat and Sun

Airports in Pensacola

1 airport
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
Direct flights go from Chicago Midway Airport to Pensacola on Monday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.
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 20m.

  • 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
8,010 reviews
Search Delta flights
SouthwestPriceFrom $216Free CancellationRating
8.0
4,253 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Pensacola

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pensacola, operating 5 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pensacola starts from $216 round-trip, up to an average price of $362. Our users have rated Southwest at 8.0/10.

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
Evergreen
Warrington

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
Fri 1/2
Fri 1/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States