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Midway

$80+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap 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 August 20, 2025.

Round-trip from

$222
(Southwest)

One-way from

$80
(Priceline)

Popular in

November

Cheapest in

May

Average price

$273

Good round-trip deal

$442 or less

Good one-way deal

$168 or less
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. 20% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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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Find 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 August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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.
Tue 9/166:30 pmPNS - MDW
1 stop4h 50mSouthwest
Tue 9/238:35 amMDW - PNS
2 stops7h 00mSouthwest
Deal found 8/19$222
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:09 pmPNS - MDW
1 stop4h 05mDelta
Wed 10/296:00 amMDW - PNS
1 stop4h 42mDelta
Deal found 8/19$223
This Southwest deal was found by Cheapflights users on 8/20. 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.
Fri 11/144:30 pmPNS - MDW
1 stop7h 40mSouthwest
Mon 11/177:00 amMDW - PNS
1 stop5h 45mSouthwest
Deal found 8/20$229
This Southwest deal was found by Cheapflights users on 8/18. 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 9/287:45 pmPNS - MDW
1 stop4h 40mSouthwest
Wed 10/19:00 amMDW - PNS
1 stop6h 35mSouthwest
Deal found 8/18$233
This Southwest deal was found by Cheapflights users on 8/18. 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 9/251:45 pmPNS - MDW
2 stops9h 05mSouthwest
Sun 9/285:30 amMDW - PNS
1 stop7h 15mSouthwest
Deal found 8/18$234
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:10 pmPNS - MDW
1 stop13h 43mMultiple Airlines
Mon 9/158:19 amMDW - PNS
1 stop9h 51mMultiple Airlines
Deal found 8/18$238
This Delta deal was found by Cheapflights users on 8/18. 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.
Thu 9/45:00 pmPNS - MDW
1 stop4h 26mDelta
Mon 9/86:00 amMDW - PNS
1 stop4h 50mDelta
Deal found 8/18$239
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:00 pmPNS - MDW
1 stop4h 26mDelta
Mon 9/156:00 amMDW - PNS
1 stop4h 50mDelta
Deal found 8/19$240
This Southwest deal was found by Cheapflights users on 8/18. 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 10/37:20 amPNS - MDW
2 stops7h 45mSouthwest
Mon 10/69:30 amMDW - PNS
2 stops12h 25mSouthwest
Deal found 8/18$245
This Southwest deal was found by Cheapflights users on 8/19. 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 9/204:45 pmPNS - MDW
Nonstop2h 10mSouthwest
Sun 9/215:30 amMDW - PNS
1 stop7h 15mSouthwest
Deal found 8/19$248

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 August 20, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.

Fly from

Pensacola

Fly to

Midway

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 9/16

6:30 pm-11:20 pm

1 stop4h 50m

Chicago Midway

Tue 9/23

8:35 am-3:35 pm

2 stops7h 00m

$222

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 10/2

7:10 pm-8:53 am

1 stop13h 43m

Chicago Midway

Mon 10/6

8:19 am-4:51 pm

1 stop8h 32m

$223

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/31

4:27 pm-10:14 pm

1 stop5h 47m

Chicago Midway

Tue 11/4

6:00 am-10:42 am

1 stop4h 42m

$223

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

4:27 pm-10:14 pm

1 stop5h 47m

Chicago Midway

Wed 10/29

6:00 am-10:42 am

1 stop4h 42m

$223

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

7:35 pm-11:15 pm

1 stop3h 40m

Chicago Midway

Sun 10/26

5:35 am-9:10 am

1 stop3h 35m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 9/12

4:03 pm-9:36 pm

1 stop5h 33m

Chicago Midway

Mon 9/15

6:30 pm-11:08 pm

1 stop4h 38m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/31

4:27 pm-10:14 pm

1 stop5h 47m

Chicago Midway

Mon 11/3

6:00 am-10:42 am

1 stop4h 42m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/10

3:38 pm-12:24 am

1 stop8h 46m

$80

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 10/24

3:38 pm-12:24 am

1 stop8h 46m

$84

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 10/16

7:30 pm-12:24 am

1 stop28h 54m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 15 results
1
2

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 month to book a flight from Pensacola to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Pensacola to Chicago Midway Airport (average of $160). Flying from Pensacola to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 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 August 20, 2025.

One of the essential ways to save on airfare from Pensacola to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 17% on airfare.

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 August 20, 2025.
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
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 4h 50m. 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 $216. Another airline that can offer you cheap pricing is Delta. These flights start at 35% 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 $68. On average you can expect to pay $323. The most popular route, (Pensacola - Chicago Midway), can usually be booked for $217.

  • 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.

  • What is the cheapest month to book a flight from Pensacola to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Pensacola to Chicago Midway Airport (average of $160). Flying from Pensacola to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$329FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$320FlexibilityNo cancel feeOn-timeN/A

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