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Pensacola

$78+ Cheap flights from Midway (MDW) to Pensacola (PNS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Mai 10 — Mai 171
So 5/10
So 5/17
1 adult, Economy
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Cheap flight deals from Midway to Pensacola

Cheapest flights from Midway to Pensacola
Explore the most affordable flight options available from Midway to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/111:33 am
MDW
-
PNS
1 stop10h 05m
Multiple Airlines
Mo 5/45:58 pm
PNS
-
MDW
2 stops17h 11m
Multiple Airlines
Deal found 4/6$269
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/98:10 am
MDW
-
PNS
Nonstop2h 15m
Southwest
Sa 5/162:50 pm
PNS
-
MDW
Nonstop2h 20m
Southwest
Deal found 4/7$271
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/259:14 am
MDW
-
PNS
1 stop12h 24m
Multiple Airlines
Mo 4/276:36 am
PNS
-
MDW
2 stops15h 43m
Multiple Airlines
Deal found 4/7$273
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:26 am
MDW
-
PNS
1 stop13h 12m
Multiple Airlines
Mo 4/274:31 pm
PNS
-
MDW
2 stops27h 00m
Multiple Airlines
Deal found 4/7$274
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/27:25 am
MDW
-
PNS
2 stops8h 50m
Southwest
Sa 5/92:50 pm
PNS
-
MDW
Nonstop2h 20m
Southwest
Deal found 4/7$286
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/238:26 am
MDW
-
PNS
1 stop7h 10m
Multiple Airlines
So 4/266:36 am
PNS
-
MDW
1 stop25h 28m
Multiple Airlines
Deal found 4/7$288
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/512:15 pm
MDW
-
PNS
1 stop8h 05m
Southwest
Di 5/124:25 pm
PNS
-
MDW
1 stop5h 50m
Southwest
Deal found 4/7$291
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/169:14 am
MDW
-
PNS
1 stop5h 26m
Frontier
So 4/1910:12 am
PNS
-
MDW
1 stop21h 52m
Frontier
Deal found 4/6$292

Find flight deals from Midway to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pensacola (PNS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(Kiwi.com)

One-way from

$78
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$334

Good round-trip deal

$317 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Chicago Midway-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Pensacola flights.
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From Chicago Midway to Pensacola
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One-way flight from Chicago Midway to Pensacola
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Pensacola.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Pensacola.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated April 10, 2026.
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

Cheapest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mi 5/6

11:35 am-8:20 pm

2 stops8h 45m

Pensacola

Sa 5/9

1:30 pm-8:05 pm

1 stop6h 35m

$296

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mo 5/4

11:40 am-7:35 pm

2 stops7h 55m

Pensacola

Sa 5/9

2:50 pm-5:10 pm

Nonstop2h 20m

$309

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Di 4/28

9:50 am-2:05 pm

1 stop4h 15m

Pensacola

Mo 5/4

5:35 am-10:25 am

1 stop4h 50m

$324

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Do 5/7

8:00 am-3:40 pm

1 stop7h 40m

Pensacola

Do 5/14

5:35 am-10:25 am

1 stop4h 50m

$342

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Do 5/14

5:10 pm-11:30 pm

1 stop6h 20m

Pensacola

Mo 5/18

6:00 am-10:00 am

1 stop4h 00m

$357

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fr 5/29

11:40 am-7:35 pm

2 stops7h 55m

Pensacola

Sa 5/30

7:10 am-2:40 pm

1 stop7h 30m

$368

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

So 4/26

6:00 am-11:55 am

1 stop5h 55m

Pensacola

Mi 4/29

5:26 pm-10:28 pm

1 stop5h 02m

$386
Quickest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mi 6/17

12:55 pm-3:05 pm

Nonstop2h 10m

Pensacola

So 6/21

5:35 pm-7:50 pm

Nonstop2h 15m

$396

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mi 6/24

12:55 pm-3:05 pm

Nonstop2h 10m

Pensacola

So 6/28

5:05 pm-12:15 am

1 stop7h 10m

$406

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fr 5/1

1:10 pm-9:00 pm

2 stops7h 50m

Pensacola

Mo 5/4

5:20 pm-10:45 pm

2 stops5h 25m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

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

Compare providers for flights from Midway to Pensacola

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Pensacola in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Pensacola flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Pensacola flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Pensacola

What is the cheapest month to book a flight from Chicago Midway Airport to Pensacola?

Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $82). Flying from Chicago Midway Airport to Pensacola in August is currently the most expensive (average of $287). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to PNS?

Find hourly flight availability from Midway to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 10, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Pensacola as you normally would.

How much does it cost to fly round-trip from Chicago Midway Airport to Pensacola?

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pensacola. Reviews last updated April 10, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Pensacola, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,337 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Delta
7.9
Good
8,393 reviews
Southwest
8.0
Very good
4,337 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

Related info for your journey

Find useful and relevant information for your journey from Midway to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pensacola from Chicago Midway?

    For a flight from Chicago Midway to Pensacola, you will be flying into Pensacola. Pensacola (PNS) is just 4.0 mi from the center of the city. Pensacola is the only Pensacola airport and it handles 0 inbound flights from Chicago Midway per day. 2 airlines have flights to Pensacola from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Pensacola?

    A quick flight from Chicago Midway Airport to Pensacola can take about 8h 45m. Southwest provides one of the quickest options available for as low as $296. Chicago Midway Airport and Pensacola are separated by a distance of 782 mi.

  • What are the cheapest airlines flying from Chicago Midway Airport to Pensacola round-trip?

    Delta, at $196, was found to be the cheapest airline from Chicago Midway Airport to Pensacola. An alternate airline flying to your destination would be Southwest. Delta is currently priced 42% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago Midway Airport to Pensacola?

    The cheapest flight price from Chicago Midway Airport to Pensacola is $138. On average you can expect to pay $278. The most popular route, (Chicago Midway - Pensacola), can usually be booked for $237.

  • Can I find deals for flights from Midway to Pensacola that include hotel bookings?

    Yes. In addition to deals on Midway to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Pensacola.

  • Can I find deals for business class flights from Midway to Pensacola?

    Yes. Cheapflights offers flight deals from Midway to Pensacola by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Pensacola?

    Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $82). Flying from Chicago Midway Airport to Pensacola in August is currently the most expensive (average of $287). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pensacola?

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

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Midway to Pensacola

Discover the top 2 airlines that operate flights from Midway to Pensacola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$273FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$207Average$363FlexibilityNo cancel feeOn-time63%

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