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Midway

$124+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
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 May 14, 2026.

This Southwest deal was found by Cheapflights users on 5/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:45 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Tue 6/1612:55 pm
MDW
-
PNS
Nonstop2h 10m
Southwest
Deal found 5/12$349
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 6/303:45 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Fri 7/37:45 am
MDW
-
PNS
Nonstop2h 15m
Southwest
Deal found 5/10$352
This Southwest deal was found by Cheapflights users on 5/9. 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 7/310:40 am
PNS
-
MDW
Nonstop2h 15m
Southwest
Sat 7/47:45 am
MDW
-
PNS
Nonstop2h 15m
Southwest
Deal found 5/9$355
This Southwest deal was found by Cheapflights users on 5/13. 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 6/103:45 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Wed 6/175:05 am
MDW
-
PNS
1 stop6h 15m
Southwest
Deal found 5/13$359
This Southwest deal was found by Cheapflights users on 5/10. 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 6/243:45 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Sat 6/276:30 am
MDW
-
PNS
1 stop6h 10m
Southwest
Deal found 5/10$362
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sun 5/245:05 pm
PNS
-
MDW
Nonstop2h 15m
Southwest
Wed 5/273:00 pm
MDW
-
PNS
1 stop4h 00m
Southwest
Deal found 5/10$365
This Delta deal was found by Cheapflights users on 5/13. 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 6/104:31 pm
PNS
-
MDW
1 stop5h 46m
Delta
Wed 6/1712:50 pm
MDW
-
PNS
1 stop5h 41m
Delta
Deal found 5/13$369
This Delta deal was found by Cheapflights users on 5/10. 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 8/16:00 am
PNS
-
MDW
1 stop4h 05m
Delta
Sat 8/84:39 pm
MDW
-
PNS
1 stop4h 58m
Delta
Deal found 5/10$375

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 May 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(Southwest)

One-way from

$124
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$409

Good round-trip deal

$398 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Pensacola-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago Midway flights.
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From Pensacola to Chicago Midway
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One-way flight from Pensacola to Chicago Midway
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Highest demand for flights based on searches. 28% potential increase in price ($143 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 2026
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Price to beat on a round-trip flight from Pensacola to Chicago Midway.
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Price to beat on a one-way flight from Pensacola to Chicago Midway.
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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 May 14, 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

Wed 6/10

4:31 pm-10:17 pm

1 stop5h 46m

Chicago Midway

Wed 6/17

12:50 pm-6:31 pm

1 stop5h 41m

$369

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 10/13

3:30 pm-9:50 pm

2 stops6h 20m

Chicago Midway

Tue 10/20

9:00 am-2:55 pm

1 stop5h 55m

$374

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/24

6:40 pm-10:35 pm

1 stop3h 55m

Chicago Midway

Sat 6/27

6:30 am-2:15 pm

2 stops7h 45m

$377

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/10

7:50 am-3:10 pm

2 stops7h 20m

Chicago Midway

Wed 6/17

10:00 am-6:05 pm

2 stops8h 05m

$379

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 7/3

11:05 am-5:50 pm

1 stop6h 45m

Chicago Midway

Sat 7/4

8:55 am-6:35 pm

2 stops9h 40m

$380

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 5/24

11:00 am-7:35 pm

2 stops8h 35m

Chicago Midway

Wed 5/27

10:15 am-7:00 pm

2 stops8h 45m

$385
Quickest round-trip

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 6/25

10:40 am-12:55 pm

Nonstop2h 15m

Chicago Midway

Tue 6/30

12:55 pm-3:05 pm

Nonstop2h 10m

$393

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 7/15

3:45 pm-6:00 pm

Nonstop2h 15m

Chicago Midway

Mon 7/27

6:40 am-11:25 am

1 stop4h 45m

$399

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 6/17

3:45 pm-6:00 pm

Nonstop2h 15m

Chicago Midway

Fri 6/19

1:00 pm-4:40 pm

1 stop3h 40m

$403

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 6/19

6:11 pm-10:17 pm

1 stop4h 06m

Chicago Midway

Tue 6/23

12:50 pm-5:06 pm

1 stop4h 16m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

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 May.
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 May 14, 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 May 14, 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
7.9
Good
4,296 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,296 reviews
Southwest
7.9
Good
4,296 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,450 reviews
Southwest
7.9
Good
4,296 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 5h 05m. There are 782 mi between Pensacola and Chicago Midway Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Delta. These flights start at 36% 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 $201. On average you can expect to pay $342. The most popular route, (Pensacola - Chicago Midway), can usually be booked for $369.

  • 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
Hammond
Porter

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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 May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$228Average$352FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$373FlexibilityNo cancel feeOn-timeN/A

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