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Midway

$90+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. 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 12/266:10 pmPNS - MDW
1 stop6h 35mSouthwest
Fri 1/25:25 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/17$304
This Southwest deal was found by Cheapflights users on 12/15. 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 12/307:20 amPNS - MDW
1 stop10h 35mSouthwest
Mon 1/55:10 amMDW - PNS
1 stop6h 15mSouthwest
Deal found 12/15$358
This Southwest deal was found by Cheapflights users on 12/15. 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 12/307:20 amPNS - MDW
1 stop10h 35mSouthwest
Sun 1/45:25 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/15$393
This Southwest deal was found by Cheapflights users on 12/16. 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.
Mon 12/2212:05 pmPNS - MDW
1 stop4h 55mSouthwest
Wed 12/245:35 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/16$399
This Southwest deal was found by Cheapflights users on 12/15. 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 12/309:50 amPNS - MDW
2 stops9h 05mSouthwest
Wed 12/315:35 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/15$404
This Southwest deal was found by Cheapflights users on 12/16. 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 12/174:15 pmPNS - MDW
1 stop6h 20mSouthwest
Wed 12/245:35 amMDW - PNS
1 stop3h 45mSouthwest
Deal found 12/16$448
This Southwest deal was found by Cheapflights users on 12/16. 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 12/1912:05 pmPNS - MDW
1 stop4h 55mSouthwest
Sat 12/205:10 amMDW - PNS
1 stop5h 50mSouthwest
Deal found 12/16$459

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$210
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

October

Cheapest in

May

Average price

$424
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. 7% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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 1/16

12:35 pm-4:29 pm

1 stop3h 54m

Chicago Midway

Mon 1/19

6:14 pm-11:13 pm

1 stop4h 59m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Tue 3/10

12:47 pm-4:35 pm

1 stop3h 48m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 1/21

1:40 pm-5:29 pm

1 stop3h 49m

Chicago Midway

Thu 1/29

6:00 am-10:26 am

1 stop4h 26m

$229

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 1/16

5:33 pm-7:27 am

2 stops13h 54m

Chicago Midway

Mon 1/19

10:07 am-4:37 pm

1 stop6h 30m

$240

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 1/25

5:33 pm-7:58 pm

1 stop26h 25m

Chicago Midway

Sat 2/14

9:15 am-7:35 am

2 stops22h 20m

$246

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 4/11

9:40 am-2:30 pm

1 stop4h 50m

Chicago Midway

Sat 4/18

10:30 am-3:15 pm

1 stop4h 45m

$249

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 2/17

7:05 am-1:00 pm

1 stop5h 55m

Chicago Midway

Sun 2/22

5:25 am-9:50 am

1 stop4h 25m

$249

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 1/25

4:25 pm-8:10 pm

1 stop3h 45m

Chicago Midway

Sat 2/14

9:20 am-4:05 pm

1 stop6h 45m

$255

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 3/16

5:25 pm-7:40 pm

Nonstop2h 15m

$105

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 5/2

5:45 pm-9:45 pm

1 stop4h 00m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 17 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 December.
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 December 18, 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 39% 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 December 18, 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
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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 3h 54m. 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 $201. Another airline that can offer you cheap pricing is Southwest. These flights start at 38% 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
Lansing
Merrillville
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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$201Average$353FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$307FlexibilityNo cancel feeOn-time63%

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