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$84+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$214
(Southwest)

One-way from

$89
(Southwest)

Popular in

March

Cheapest in

January

Average price

$370

Good round-trip deal

$268 or less

Good one-way deal

$138 or less
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. 6% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago Midway to Pensacola.
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Price to beat on a one-way 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/9. 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.
Sat 9/68:15 amMDW - PNS
1 stop6h 50mSouthwest
Mon 9/84:35 pmPNS - MDW
1 stop6h 15mSouthwest
Deal found 6/9$214
This Delta deal was found by Cheapflights users on 6/12. 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 9/296:00 amMDW - PNS
1 stop4h 46mDelta
Tue 10/77:00 amPNS - MDW
2 stops11h 36mDelta
Deal found 6/12$236
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/111:11 pmMDW - PNS
2 stops23h 37mMultiple Airlines
Thu 8/143:50 pmPNS - MDW
2 stops26h 27mMultiple Airlines
Deal found 6/10$308
This Booking.com deal was found by Cheapflights users on 6/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/122:44 pmMDW - PNS
1 stop24h 45mFrontier
Sat 6/144:29 pmPNS - MDW
1 stop28h 24mFrontier
Deal found 6/9$384

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 June 12, 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 9/6

8:15 am-3:05 pm

1 stop6h 50m

Pensacola

Mon 9/8

4:35 pm-10:50 pm

1 stop6h 15m

$214

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 9/29

6:00 am-10:46 am

1 stop4h 46m

Pensacola

Wed 10/8

6:00 am-6:36 pm

2 stops12h 36m

$236

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 8/11

1:11 pm-12:48 pm

2 stops23h 37m

Pensacola

Thu 8/14

3:50 pm-6:17 pm

2 stops26h 27m

$308

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 8/29

6:31 pm-3:05 pm

1 stop20h 34m

Pensacola

Mon 9/1

4:00 pm-12:24 am

1 stop8h 24m

$525

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/11

10:50 am-3:35 pm

1 stop4h 45m

$84

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 10/25

6:00 am-12:50 pm

1 stop6h 50m

$126

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 7/10

2:44 pm-3:34 pm

1 stop24h 50m

$141

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 7/18

10:31 am-6:29 pm

2 stops31h 58m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 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
4,287 reviews

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Boarding

8.2

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
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Boarding

8.2

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
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Entertainment

7.6

Boarding

8.2

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 1 inbound flight 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 $214, 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 38% 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 $89. Users have also found prices from $126 and $141 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 $88. On average you can expect to pay $246. The most popular route, (Chicago Midway - Pensacola), can usually be booked for $177.

  • 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
Navarre Beach
Warrington

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Alternative routes for Midway to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$340FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$248Average$381FlexibilityNo cancel feeOn-time63%

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