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$105+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
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 March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Southwest)

One-way from

$105
(Southwest)

Popular in

November

Cheapest in

April

Average price

$431

Good round-trip deal

$305 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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Highest demand for flights based on searches. 15% potential increase in price ($62 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 March 2025
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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 March 25, 2025.

This Southwest deal was found by Cheapflights users on 3/24. 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 4/225:30 amMDW - PNS
1 stop6h 35mSouthwest
Tue 4/293:05 pmPNS - MDW
1 stop6h 50mSouthwest
Deal found 3/24$217
This Delta deal was found by Cheapflights users on 3/22. 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 7/221:05 pmMDW - PNS
1 stop4h 58mDelta
Tue 7/298:05 amPNS - MDW
1 stop6h 51mDelta
Deal found 3/22$229
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Wed 4/26:40 amMDW - PNS
1 stop11h 47mFrontier
Fri 4/47:23 pmPNS - MDW
1 stop28h 58mFrontier
Deal found 3/23$290
This Mytrip deal was found by Cheapflights users on 3/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2411:08 amMDW - PNS
3 stops29h 44mMultiple Airlines
Sat 4/268:43 amPNS - MDW
3 stops24h 35mMultiple Airlines
Deal found 3/22$616

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 March 25, 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

Tue 4/22

5:30 am-12:05 pm

1 stop6h 35m

Pensacola

Tue 4/29

3:05 pm-9:55 pm

1 stop6h 50m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 7/22

1:05 pm-6:03 pm

1 stop4h 58m

Pensacola

Tue 7/29

8:05 am-2:56 pm

1 stop6h 51m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 4/4

6:45 am-6:23 pm

1 stop11h 38m

Pensacola

Mon 4/14

7:23 pm-12:21 am

1 stop28h 58m

$320

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 4/24

11:08 am-4:52 pm

3 stops29h 44m

Pensacola

Sat 4/26

8:43 am-9:18 am

3 stops24h 35m

$616

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 5/11

10:45 am-1:00 pm

Nonstop2h 15m

$105

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 6/2

6:00 am-10:35 am

1 stop4h 35m

$109

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 5/4

8:03 pm-3:28 pm

1 stop19h 25m

$136

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 4/10

5:15 am-6:55 pm

1 stop13h 40m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $306). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $418). 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 March 25, 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.

Rainfall in Pensacola by month

Plan your trip to Pensacola by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pensacola ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Pensacola when rainfall is around 4.2 in.

Temperature in Pensacola by month

Plan your trip to Pensacola by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pensacola, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 March 25, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier from Chicago to Pensacola by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

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
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

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.
Frontier
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

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.

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

    Southwest, at $217, was found to be the cheapest airline from Chicago Midway Airport to Pensacola.Alternate airlines to your destination round-trip include Delta and Frontier. Southwest is currently priced 37% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Pensacola one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $105. Users have also found prices from $109 and $136 on Delta and Frontier, respectively.

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

    The cheapest flight price from Chicago Midway Airport to Pensacola is $263. On average you can expect to pay $429. The most popular route, (Chicago Midway - Pensacola), can usually be booked for $217.

  • 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 $306). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $418). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
Milton
Atmore
Navarre Beach
Warrington

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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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$228Average$363FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$263Average$410FlexibilityNo cancel feeOn-time63%
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