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Pensacola

$66+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$204
(Southwest)

One-way from

$66
(Southwest)

Popular in

March

Cheapest in

January

Average price

$241
From Chicago Midway to Pensacola
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One-way flight from Chicago Midway to Pensacola
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Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 9/295:40 amMDW - PNS
1 stop3h 35mSouthwest
Wed 10/17:35 amPNS - MDW
2 stops7h 25mSouthwest
Deal found 9/11$204
This Southwest deal was found by Cheapflights users on 9/8. 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 10/45:45 amMDW - PNS
1 stop5h 25mSouthwest
Wed 10/82:30 pmPNS - MDW
1 stop3h 40mSouthwest
Deal found 9/8$205
This Southwest deal was found by Cheapflights users on 9/10. 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 10/225:15 amMDW - PNS
1 stop7h 25mSouthwest
Sat 10/255:40 pmPNS - MDW
1 stop4h 45mSouthwest
Deal found 9/10$211
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/186:00 amMDW - PNS
1 stop4h 39mDelta
Tue 10/2811:47 amPNS - MDW
1 stop4h 22mDelta
Deal found 9/10$218
This Southwest deal was found by Cheapflights users on 9/10. 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 10/2412:55 pmMDW - PNS
1 stop5h 55mSouthwest
Sun 10/268:25 pmPNS - MDW
1 stop3h 45mSouthwest
Deal found 9/10$220
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:30 pmMDW - PNS
1 stop27h 05mFrontier
Sun 11/24:30 pmPNS - MDW
1 stop19h 00mFrontier
Deal found 9/11$227
This Southwest deal was found by Cheapflights users on 9/11. 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 10/179:15 amMDW - PNS
1 stop9h 35mSouthwest
Mon 10/207:35 pmPNS - MDW
1 stop3h 40mSouthwest
Deal found 9/11$234
This Southwest deal was found by Cheapflights users on 9/9. 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 10/2412:55 pmMDW - PNS
1 stop5h 55mSouthwest
Mon 10/277:20 amPNS - MDW
2 stops7h 45mSouthwest
Deal found 9/9$235
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 10/2012:48 pmMDW - PNS
1 stop4h 10mDelta
Sat 10/2512:13 pmPNS - MDW
1 stop6h 12mDelta
Deal found 9/10$248
This Delta deal was found by Cheapflights users on 9/9. 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.
Tue 9/2312:43 pmMDW - PNS
1 stop6h 34mDelta
Fri 9/264:03 pmPNS - MDW
1 stop5h 33mDelta
Deal found 9/9$249

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 September 11, 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

Sat 10/4

5:45 am-11:10 am

1 stop5h 25m

Pensacola

Wed 10/8

2:30 pm-6:10 pm

1 stop3h 40m

$205

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/8

5:15 am-12:40 pm

1 stop7h 25m

Pensacola

Wed 10/15

5:15 pm-11:35 pm

1 stop6h 20m

$205

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 10/18

6:00 am-10:39 am

1 stop4h 39m

Pensacola

Tue 10/28

11:47 am-4:09 pm

1 stop4h 22m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 10/24

9:30 am-9:55 pm

2 stops12h 25m

Pensacola

Mon 10/27

6:05 pm-12:45 am

1 stop6h 40m

$243

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 10/20

12:48 pm-4:58 pm

1 stop4h 10m

Pensacola

Wed 10/22

4:20 pm-10:14 pm

1 stop5h 54m

$248

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 11/1

10:40 am-3:05 pm

1 stop4h 25m

Pensacola

Sun 11/2

5:00 am-8:45 am

1 stop3h 45m

$248

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 10/20

12:48 pm-4:58 pm

1 stop4h 10m

Pensacola

Sat 10/25

12:13 pm-6:25 pm

1 stop6h 12m

$248

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 9/23

12:43 pm-7:17 pm

1 stop6h 34m

Pensacola

Fri 9/26

4:03 pm-9:36 pm

1 stop5h 33m

$249

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/18

10:50 am-3:35 pm

1 stop4h 45m

$66

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 12/10

5:35 am-9:20 am

1 stop3h 45m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 16 results
1
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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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $303). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $415). 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 September 11, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 45% 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 September 11, 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
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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 39m. Southwest provides one of the quickest options available for as low as $218. 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 44% 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $303). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $415). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$308FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$370FlexibilityNo cancel feeOn-time63%

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