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Midway

$149+ Cheap flights from Pensacola (PNS) to Midway (MDW)

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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Cheap flight deals from Pensacola to Midway

Cheapest flights from Pensacola to Midway
Explore the most affordable flight options available from Pensacola to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.

This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:55 am
PNS
-
MDW
1 stop5h 35m
Southwest
Wed 9/22:00 pm
MDW
-
PNS
1 stop3h 35m
Southwest
Deal found 7/22$292
This Delta deal was found by Cheapflights users on 7/20. 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 9/55:00 pm
PNS
-
MDW
1 stop5h 36m
Delta
Sun 9/66:05 am
MDW
-
PNS
1 stop6h 45m
Delta
Deal found 7/20$297
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:55 am
PNS
-
MDW
2 stops7h 55m
Southwest
Sat 9/126:45 am
MDW
-
PNS
1 stop5h 05m
Southwest
Deal found 7/22$302
This Southwest deal was found by Cheapflights users on 7/21. 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 8/267:00 am
PNS
-
MDW
2 stops8h 30m
Southwest
Tue 9/110:10 am
MDW
-
PNS
2 stops8h 25m
Southwest
Deal found 7/21$307
This Southwest deal was found by Cheapflights users on 7/19. 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 9/59:40 am
PNS
-
MDW
2 stops10h 50m
Southwest
Sun 9/68:35 am
MDW
-
PNS
1 stop8h 25m
Southwest
Deal found 7/19$308
This Southwest deal was found by Cheapflights users on 7/21. 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 10/147:55 am
PNS
-
MDW
2 stops6h 30m
Southwest
Sat 10/176:35 am
MDW
-
PNS
2 stops12h 05m
Southwest
Deal found 7/21$313
This Southwest deal was found by Cheapflights users on 7/21. 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 8/1510:50 am
PNS
-
MDW
1 stop5h 05m
Southwest
Mon 8/175:30 am
MDW
-
PNS
1 stop7h 00m
Southwest
Deal found 7/21$315
This Southwest deal was found by Cheapflights users on 7/20. 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 9/210:20 am
PNS
-
MDW
1 stop6h 35m
Southwest
Sun 9/68:35 am
MDW
-
PNS
1 stop8h 25m
Southwest
Deal found 7/20$320
This Southwest deal was found by Cheapflights users on 7/19. 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 9/129:40 am
PNS
-
MDW
1 stop4h 40m
Southwest
Tue 9/152:00 pm
MDW
-
PNS
1 stop3h 35m
Southwest
Deal found 7/19$324
This Delta deal was found by Cheapflights users on 7/21. 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 9/16:00 am
PNS
-
MDW
1 stop3h 59m
Delta
Sat 9/54:39 pm
MDW
-
PNS
1 stop4h 58m
Delta
Deal found 7/21$325

Find flight deals from Pensacola to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Midway (MDW). 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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$292
(Southwest)

One-way from

$149
(Southwest)

Popular in

March

Cheapest in

June

Average price

$397

Good round-trip deal

$447 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Pensacola-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pensacola-Chicago Midway flights.
Search Deals
From Pensacola to Chicago Midway
Search Deals
One-way flight from Pensacola to Chicago Midway
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Pensacola to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Pensacola to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola to Midway 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 July 23, 2026.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 9/17

4:20 pm-10:25 pm

1 stop6h 05m

Chicago Midway

Sat 9/19

6:45 am-11:45 am

1 stop5h 00m

$297

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 9/1

3:00 pm-11:10 pm

2 stops8h 10m

Chicago Midway

Sat 9/5

6:35 am-10:10 am

1 stop3h 35m

$302

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 8/13

2:40 pm-11:20 pm

2 stops8h 40m

Chicago Midway

Mon 8/17

7:55 am-12:10 pm

1 stop4h 15m

$302

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 10/14

7:55 am-2:25 pm

2 stops6h 30m

Chicago Midway

Sat 10/17

6:45 am-1:35 pm

1 stop6h 50m

$302

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 9/5

9:40 am-8:30 pm

2 stops10h 50m

Chicago Midway

Sun 9/6

8:35 am-5:00 pm

1 stop8h 25m

$308
Quickest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/26

7:00 am-12:15 pm

1 stop5h 15m

Chicago Midway

Sat 8/29

6:35 am-10:10 am

1 stop3h 35m

$333

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 11/12

2:15 pm-8:50 pm

1 stop6h 35m

Chicago Midway

Sat 11/14

6:00 am-4:20 pm

2 stops10h 20m

$338

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 9/22

7:00 am-3:30 pm

2 stops8h 30m

Chicago Midway

Sat 9/26

10:25 am-4:15 pm

1 stop5h 50m

$338

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 8/13

6:00 am-9:59 am

1 stop3h 59m

Chicago Midway

Mon 8/17

5:10 pm-11:44 pm

1 stop6h 34m

$366
Cheapest one-way

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 9/24

9:26 am-4:15 pm

1 stop6h 49m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Pensacola to Midway

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 Pensacola to Midway in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Pensacola-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Chicago Midway Airport 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 Pensacola-Chicago Midway Airport 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 Pensacola to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pensacola 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 Pensacola to Chicago Midway Airport

What is the cheapest time of day to fly from PNS to MDW?

Find hourly flight availability from Pensacola to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pensacola to Chicago Midway Airport as you normally would.

How much does it cost to fly round-trip from Pensacola to Chicago Midway Airport?

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 23, 2026.
See what other customers who have flown with Southwest and Delta from Pensacola to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,479 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Pensacola to Midway. 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 from for flights from Pensacola to Chicago Midway?

    Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Chicago Midway from Pensacola. Booking flights from Pensacola (PNS) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 2 different airlines.

  • How long is the flight from Pensacola to Chicago Midway Airport?

    Departing from Pensacola to Chicago Midway Airport will take you 6h 05m. There are 782 mi between Pensacola and Chicago Midway Airport.

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

    Cheapflights users have booked flights from Pensacola to Chicago Midway Airport round-trip from $228. Another airline that can offer you cheap pricing is Southwest. These flights start at 39% lower than the current average price 3 months from now.

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

    The cheapest flight price from Pensacola to Chicago Midway Airport is $209. On average you can expect to pay $348. The most popular route, (Pensacola - Chicago Midway), can usually be booked for $292.

  • Can I find deals for flights from Pensacola to Midway that include hotel bookings?

    Yes. In addition to deals on Pensacola to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pensacola to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pensacola to Midway.

  • Can I find deals for business class flights from Pensacola to Midway?

    Yes. Cheapflights offers flight deals from Pensacola to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Pensacola to Midway

Discover the top 2 airlines that operate flights from Pensacola to Midway. 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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$228Average$388FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$237Average$397FlexibilityNo cancel feeOn-time63%

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