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Pensacola

$70+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Southwest deal was found by Cheapflights users on 12/3. 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.
Mon 12/225:25 amMDW - PNS
1 stop3h 45mSouthwest
Wed 12/244:15 pmPNS - MDW
1 stop4h 00mSouthwest
Deal found 12/3$269
This Southwest deal was found by Cheapflights users on 12/2. 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.
Sun 12/285:25 amMDW - PNS
1 stop3h 45mSouthwest
Wed 1/77:50 amPNS - MDW
2 stops11h 00mSouthwest
Deal found 12/2$274
This Southwest deal was found by Cheapflights users on 12/2. 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 12/1312:00 pmMDW - PNS
1 stop5h 00mSouthwest
Tue 12/169:55 amPNS - MDW
1 stop6h 55mSouthwest
Deal found 12/2$304
This Southwest deal was found by Cheapflights users on 12/1. 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.
Fri 12/195:25 amMDW - PNS
1 stop3h 45mSouthwest
Fri 12/266:10 pmPNS - MDW
1 stop6h 35mSouthwest
Deal found 12/1$324
This Southwest deal was found by Cheapflights users on 12/2. 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 12/205:10 amMDW - PNS
2 stops9h 45mSouthwest
Wed 12/244:15 pmPNS - MDW
1 stop4h 00mSouthwest
Deal found 12/2$333
This Delta deal was found by Cheapflights users on 12/3. 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 12/176:00 amMDW - PNS
1 stop6h 41mDelta
Thu 1/15:31 pmPNS - MDW
1 stop4h 51mDelta
Deal found 12/3$334
This Delta deal was found by Cheapflights users on 12/4. 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.
Fri 12/126:00 amMDW - PNS
1 stop6h 41mDelta
Sun 12/147:15 amPNS - MDW
1 stop4h 40mDelta
Deal found 12/4$339
This Southwest deal was found by Cheapflights users on 12/4. 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.
Fri 12/195:25 amMDW - PNS
1 stop3h 45mSouthwest
Sun 12/211:55 pmPNS - MDW
2 stops9h 10mSouthwest
Deal found 12/4$354
This Southwest deal was found by Cheapflights users on 12/3. 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 12/256:55 amMDW - PNS
1 stop5h 50mSouthwest
Wed 12/314:15 pmPNS - MDW
1 stop4h 00mSouthwest
Deal found 12/3$358

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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$220
(Southwest)

One-way from

$70
(Southwest)

Popular in

November

Cheapest in

September

Average price

$385
Provider with most accurate pricing for Chicago Midway-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Pensacola flights.
Search Deals
From Chicago Midway to Pensacola
Search Deals
One-way flight from Chicago Midway to Pensacola
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.

Fly from

Midway

Fly to

Pensacola

Route

Depart

Return

Price

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

Fri 1/2

5:00 am-11:15 am

1 stop6h 15m

Pensacola

Tue 1/6

4:00 pm-10:05 pm

1 stop6h 05m

$239

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 1/9

6:00 am-9:50 am

1 stop3h 50m

Pensacola

Mon 1/12

10:25 am-4:35 pm

2 stops6h 10m

$245

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 2/7

6:00 am-1:50 pm

2 stops7h 50m

Pensacola

Fri 2/13

1:10 pm-8:55 pm

2 stops7h 45m

$246

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 2/26

12:46 pm-6:19 pm

1 stop5h 33m

Pensacola

Sun 3/1

4:04 pm-10:42 pm

1 stop6h 38m

$264

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 12/22

5:25 am-9:10 am

1 stop3h 45m

Pensacola

Thu 12/25

4:15 pm-10:35 pm

1 stop6h 20m

$269

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 12/28

5:25 am-9:10 am

1 stop3h 45m

Pensacola

Wed 1/7

7:50 am-1:20 pm

1 stop5h 30m

$269

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 12/22

5:25 am-9:10 am

1 stop3h 45m

Pensacola

Wed 12/24

4:15 pm-8:15 pm

1 stop4h 00m

$269

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 12/16

6:00 am-10:37 am

1 stop4h 37m

Pensacola

Thu 12/18

6:00 am-9:54 am

1 stop3h 54m

$304

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 12/19

5:25 am-9:10 am

1 stop3h 45m

Pensacola

Sun 12/21

6:10 pm-12:45 am

1 stop6h 35m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 22 results
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2
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Pensacola flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $81). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $254). 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 December 4, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 44% on flights from Chicago Midway Airport to Pensacola by exploring options for tickets in the evening.

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 December 4, 2025.
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
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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 5h 33m. Southwest provides one of the quickest options available for as low as $264. 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?

    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 43% below the average price you’ll pay for this route.

  • 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 $81). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $254). 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
Perdido Key
Navarre Beach
Warrington

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Alternative routes for Midway to Pensacola

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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$273FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$362FlexibilityNo cancel feeOn-time63%

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