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Pensacola

$88+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Southwest)

One-way from

$88
(Southwest)

Popular in

March

Cheapest in

September

Average price

$378

Good round-trip deal

$319 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
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago Midway to Pensacola.
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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 January 8, 2026.

This Southwest deal was found by Cheapflights users on 1/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:00 amMDW - PNS
Nonstop2h 15mSouthwest
Fri 3/135:25 pmPNS - MDW
Nonstop2h 15mSouthwest
Deal found 1/6$209
This Southwest deal was found by Cheapflights users on 1/7. 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.
Thu 4/167:30 amMDW - PNS
1 stop5h 55mSouthwest
Sun 4/194:50 pmPNS - MDW
Nonstop2h 15mSouthwest
Deal found 1/7$210
This Southwest deal was found by Cheapflights users on 1/7. 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.
Thu 3/197:45 amMDW - PNS
1 stop4h 20mSouthwest
Mon 3/303:00 pmPNS - MDW
1 stop5h 45mSouthwest
Deal found 1/7$211
This Delta deal was found by Cheapflights users on 1/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1812:45 pmMDW - PNS
1 stop5h 57mDelta
Tue 2/245:48 pmPNS - MDW
1 stop4h 45mDelta
Deal found 1/7$212
This Southwest deal was found by Cheapflights users on 1/7. 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.
Tue 2/246:10 amMDW - PNS
2 stops9h 05mSouthwest
Fri 2/271:10 pmPNS - MDW
2 stops7h 45mSouthwest
Deal found 1/7$213
This Southwest deal was found by Cheapflights users on 1/7. 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.
Wed 4/11:30 pmMDW - PNS
2 stops7h 10mSouthwest
Mon 4/63:00 pmPNS - MDW
1 stop5h 45mSouthwest
Deal found 1/7$216
This Southwest deal was found by Cheapflights users on 1/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:00 amMDW - PNS
1 stop3h 50mSouthwest
Mon 2/234:25 pmPNS - MDW
1 stop3h 45mSouthwest
Deal found 1/6$218
This Delta deal was found by Cheapflights users on 1/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:00 amMDW - PNS
1 stop4h 26mDelta
Sat 2/79:23 amPNS - MDW
1 stop6h 15mDelta
Deal found 1/7$220
This Southwest deal was found by Cheapflights users on 1/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1710:30 amMDW - PNS
2 stops9h 35mSouthwest
Sat 3/217:55 pmPNS - MDW
1 stop4h 10mSouthwest
Deal found 1/6$222
This Southwest deal was found by Cheapflights users on 1/7. 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.
Thu 2/195:25 amMDW - PNS
1 stop4h 00mSouthwest
Sat 2/2110:15 amPNS - MDW
2 stops6h 55mSouthwest
Deal found 1/7$225
This Southwest deal was found by Cheapflights users on 1/5. 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 4/95:30 amMDW - PNS
1 stop3h 45mSouthwest
Sat 4/119:40 amPNS - MDW
1 stop9h 40mSouthwest
Deal found 1/5$226

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 January 8, 2026.
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 4/1

6:00 am-1:50 pm

1 stop7h 50m

Pensacola

Mon 4/6

3:00 pm-8:45 pm

1 stop5h 45m

$211

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 2/24

6:10 am-3:15 pm

2 stops9h 05m

Pensacola

Fri 2/27

1:10 pm-8:55 pm

2 stops7h 45m

$213

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 3/19

7:45 am-12:05 pm

1 stop4h 20m

Pensacola

Mon 3/30

5:25 pm-7:40 pm

Nonstop2h 15m

$219

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/20

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Mon 2/23

5:48 pm-10:31 pm

1 stop4h 43m

$220

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 2/16

5:15 am-12:35 pm

1 stop7h 20m

Pensacola

Sat 2/21

10:15 am-5:10 pm

2 stops6h 55m

$225

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/6

6:14 pm-11:13 pm

1 stop4h 59m

Pensacola

Sun 2/8

6:00 am-9:53 am

1 stop3h 53m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/18

6:00 am-12:30 pm

1 stop6h 30m

Pensacola

Mon 2/23

4:04 pm-10:31 pm

1 stop6h 27m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 3/1

6:40 pm-11:11 pm

1 stop4h 31m

Pensacola

Sat 3/7

6:00 am-10:21 am

1 stop4h 21m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 3/7

3:00 pm-9:55 pm

1 stop6h 55m

Pensacola

Fri 3/13

5:55 pm-12:05 am

1 stop6h 10m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 4/8

8:00 am-2:30 pm

1 stop6h 30m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 20 results
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 January.
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 $265). 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.

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 January 8, 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
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,025 reviews
Southwest
8.0
Very good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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 6h 30m. Southwest provides one of the quickest options available for as low as $220. 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.

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

    The cheapest flight price from Chicago Midway Airport to Pensacola is $209. On average you can expect to pay $338. The most popular route, (Chicago Midway - Pensacola), can usually be booked for $174.

  • 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 $265). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$298FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$214Average$362FlexibilityNo cancel feeOn-time63%

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