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Pensacola

$144+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
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 August 1, 2026.

This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 8/262:00 pm
MDW
-
PNS
1 stop3h 35m
Southwest
Sat 8/299:40 am
PNS
-
MDW
1 stop4h 40m
Southwest
Deal found 7/28$288
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 9/92:00 pm
MDW
-
PNS
1 stop3h 35m
Southwest
Wed 9/163:00 pm
PNS
-
MDW
1 stop5h 45m
Southwest
Deal found 7/30$292
This Southwest deal was found by Cheapflights users on 7/30. 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.
Tue 9/12:00 pm
MDW
-
PNS
1 stop3h 35m
Southwest
Sun 9/65:55 pm
PNS
-
MDW
1 stop5h 00m
Southwest
Deal found 7/30$293
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/209:50 am
MDW
-
PNS
1 stop4h 15m
Southwest
Mon 8/2410:05 am
PNS
-
MDW
1 stop6h 50m
Southwest
Deal found 7/29$297
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:54 am
MDW
-
PNS
1 stop6h 18m
Delta
Sun 8/306:00 am
PNS
-
MDW
1 stop5h 51m
Delta
Deal found 7/31$299
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 8/205:00 am
MDW
-
PNS
2 stops8h 05m
Southwest
Sun 8/236:50 pm
PNS
-
MDW
1 stop5h 20m
Southwest
Deal found 7/30$303
This Southwest deal was found by Cheapflights users on 7/31. 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.
Thu 8/275:55 am
MDW
-
PNS
1 stop3h 35m
Southwest
Mon 8/312:40 pm
PNS
-
MDW
2 stops8h 40m
Southwest
Deal found 7/31$304
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/127:55 am
MDW
-
PNS
2 stops8h 55m
Southwest
Sat 9/199:40 am
PNS
-
MDW
2 stops10h 55m
Southwest
Deal found 7/29$307

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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$288
(Southwest)

One-way from

$144
(Southwest)

Popular in

March

Cheapest in

November

Average price

$386

Good round-trip deal

$414 or less

Good one-way deal

$281 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
Search Deals
One-way flight from Chicago Midway to Pensacola
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 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 August 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.
Search Deals

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 August 1, 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

Sat 9/12

6:45 am-11:50 am

1 stop5h 05m

Pensacola

Sat 9/19

9:40 am-2:20 pm

1 stop4h 40m

$292
Quickest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/21

6:04 am-10:52 am

1 stop4h 48m

Pensacola

Tue 10/27

8:05 am-11:50 am

1 stop3h 45m

$297

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 9/16

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Sat 9/19

9:40 am-8:35 pm

2 stops10h 55m

$298

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 9/15

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Tue 9/22

7:00 am-3:20 pm

2 stops8h 20m

$300

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 10/5

8:30 am-4:35 pm

2 stops8h 05m

Pensacola

Tue 10/6

7:55 am-2:25 pm

2 stops6h 30m

$307

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 10/30

9:55 am-5:25 pm

2 stops7h 30m

Pensacola

Mon 11/2

2:15 pm-10:55 pm

2 stops8h 40m

$308

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 10/9

6:05 pm-10:50 pm

1 stop4h 45m

Pensacola

Sun 10/11

7:45 am-3:40 pm

2 stops7h 55m

$343

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 10/2

1:00 pm-4:46 pm

1 stop3h 46m

Pensacola

Tue 10/6

7:02 am-11:50 am

1 stop4h 48m

$346
Cheapest one-way

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 8/26

12:46 pm-7:20 pm

1 stop6h 34m

$149
Quickest one-way

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/5

6:35 am-10:10 am

1 stop3h 35m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 19 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 August.
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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $132). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $493). 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 August 1, 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.

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 August 1, 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
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.8
Good
8,497 reviews
Southwest
8.0
Very good
4,229 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 4h 48m. Southwest provides one of the quickest options available for as low as $297. Chicago Midway Airport and Pensacola are separated by a distance of 782 mi. This flight may include one or multiple stops.

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

    Southwest, at $207, was found to be the cheapest airline from Chicago Midway Airport to Pensacola. An alternate airline flying to your destination would be Delta. Southwest is currently priced 41% 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 $167. On average you can expect to pay $390. The most popular route, (Chicago Midway - Pensacola), can usually be booked for $293.

  • 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $132). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $493). 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

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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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$207Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$311FlexibilityNo cancel feeOn-timeN/A

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