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Midway

$95+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Southwest)

One-way from

$95
(Kiwi.com)

Popular in

October

Cheapest in

May

Average price

$446
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. 9% potential increase in price ($35 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 October 2025
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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 October 27, 2025.

This Southwest deal was found by Cheapflights users on 10/24. 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.
Fri 12/1212:10 pmPNS - MDW
1 stop6h 30mSouthwest
Tue 12/1610:50 amMDW - PNS
1 stop4h 45mSouthwest
Deal found 10/24$224
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/35:54 pmPNS - MDW
1 stop28h 04mMultiple Airlines
Mon 12/88:42 pmMDW - PNS
2 stops16h 31mMultiple Airlines
Deal found 10/26$225
This Delta deal was found by Cheapflights users on 10/26. 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 12/47:15 amPNS - MDW
1 stop4h 40mDelta
Thu 12/116:00 amMDW - PNS
1 stop6h 41mDelta
Deal found 10/26$229
This Southwest deal was found by Cheapflights users on 10/26. 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 12/44:15 pmPNS - MDW
1 stop6h 20mSouthwest
Mon 12/85:35 amMDW - PNS
2 stops10h 00mSouthwest
Deal found 10/26$234
This Delta deal was found by Cheapflights users on 10/26. 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 11/147:09 pmPNS - MDW
1 stop4h 31mDelta
Mon 11/1712:47 pmMDW - PNS
1 stop5h 17mDelta
Deal found 10/26$239
This Southwest deal was found by Cheapflights users on 10/24. 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.
Fri 11/74:30 pmPNS - MDW
1 stop5h 20mSouthwest
Tue 11/1110:50 amMDW - PNS
1 stop4h 45mSouthwest
Deal found 10/24$244
This Delta deal was found by Cheapflights users on 10/25. 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 11/89:46 amPNS - MDW
1 stop5h 40mDelta
Sun 11/96:00 amMDW - PNS
1 stop4h 41mDelta
Deal found 10/25$249
This Delta deal was found by Cheapflights users on 10/25. 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 12/2511:05 amPNS - MDW
1 stop6h 21mDelta
Thu 1/16:00 amMDW - PNS
1 stop4h 20mDelta
Deal found 10/25$250
This Southwest deal was found by Cheapflights users on 10/26. 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 12/39:55 amPNS - MDW
2 stops7h 05mSouthwest
Sun 12/75:10 amMDW - PNS
1 stop6h 15mSouthwest
Deal found 10/26$255
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Fri 11/1411:17 amPNS - MDW
1 stop23h 09mMultiple Airlines
Sun 11/1611:21 amMDW - PNS
2 stops23h 01mMultiple Airlines
Deal found 10/25$256
This Southwest deal was found by Cheapflights users on 10/26. 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 12/39:55 amPNS - MDW
2 stops7h 05mSouthwest
Mon 12/85:35 amMDW - PNS
2 stops10h 00mSouthwest
Deal found 10/26$260
This Delta deal was found by Cheapflights users on 10/26. 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 11/107:09 pmPNS - MDW
1 stop4h 31mDelta
Fri 11/146:00 amMDW - PNS
1 stop6h 41mDelta
Deal found 10/26$269

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 October 27, 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

Fri 12/12

12:10 pm-6:40 pm

1 stop6h 30m

Chicago Midway

Tue 12/16

10:50 am-3:35 pm

1 stop4h 45m

$224

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 12/3

5:54 pm-9:58 pm

1 stop28h 04m

Chicago Midway

Mon 12/8

8:42 pm-1:13 pm

2 stops16h 31m

$225

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 11/24

8:00 am-11:52 am

1 stop3h 52m

Chicago Midway

Mon 12/1

6:00 am-12:41 pm

1 stop6h 41m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 12/4

7:15 am-11:55 am

1 stop4h 40m

Chicago Midway

Sat 12/13

6:00 am-10:41 am

1 stop4h 41m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 11/26

7:10 pm-11:40 pm

1 stop4h 30m

Chicago Midway

Wed 12/3

6:00 am-10:41 am

1 stop4h 41m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 12/12

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Mon 12/15

5:29 pm-11:11 pm

1 stop5h 42m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 12/6

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Sun 12/7

10:49 am-2:45 pm

1 stop3h 56m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 11/14

7:09 pm-11:40 pm

1 stop4h 31m

Chicago Midway

Sun 11/16

6:00 am-10:41 am

1 stop4h 41m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 12/18

9:45 am-6:40 pm

2 stops8h 55m

Chicago Midway

Mon 12/22

5:25 am-9:10 am

1 stop3h 45m

$234

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 11/15

7:50 am-2:05 pm

1 stop6h 15m

Chicago Midway

Sun 11/16

5:10 am-11:25 am

1 stop6h 15m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 20 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 Pensacola-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pensacola-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 27, 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 evening could potentially save you up to 41% 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 October 27, 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
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
7.9
Good
7,996 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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 3h 52m. 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 34% lower than the current average price 3 months from now.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$307FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$355FlexibilityNo cancel feeOn-timeN/A

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