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$99+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$217
(Delta)

One-way from

$99
(Southwest)

Popular in

June

Cheapest in

May

Average price

$355

Good round-trip deal

$277 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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High demand for flights, 0% potential price rise
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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 July 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 July 3, 2025.

This Delta deal was found by Cheapflights users on 7/3. 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 8/205:00 pmPNS - MDW
1 stop4h 44mDelta
Tue 8/264:25 pmMDW - PNS
1 stop5h 21mDelta
Deal found 7/3$217
This Southwest deal was found by Cheapflights users on 7/2. 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 10/163:20 pmPNS - MDW
2 stops7h 55mSouthwest
Thu 10/301:45 pmMDW - PNS
1 stop3h 45mSouthwest
Deal found 7/2$222
This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/75:21 pmPNS - MDW
1 stop22h 32mFrontier
Fri 9/124:48 pmMDW - PNS
1 stop23h 38mFrontier
Deal found 7/1$281

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 3, 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

Wed 8/20

5:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Tue 8/26

4:25 pm-9:46 pm

1 stop5h 21m

$217

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 8/21

7:20 am-2:50 pm

2 stops7h 30m

Chicago Midway

Mon 8/25

5:45 am-11:45 am

1 stop6h 00m

$222

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sun 9/7

5:21 pm-3:53 pm

1 stop22h 32m

Chicago Midway

Fri 9/12

4:48 pm-4:26 pm

1 stop23h 38m

$281

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 8/4

2:25 pm-4:40 pm

Nonstop2h 15m

$99

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 8/22

4:00 pm-12:24 am

1 stop8h 24m

$106

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 9/13

9:22 am-3:26 pm

1 stop6h 04m

$126

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 8/2

6:00 am-8:22 pm

1 stop14h 22m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 July 3, 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 14% 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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier 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
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

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
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

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
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

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.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

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.

  • 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 $217. Other airlines that can offer you cheap pricing are Southwest, from $222, and Frontier, from $281. These flights start at 37% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Pensacola to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Pensacola to Chicago Midway Airport are Southwest ($99), Frontier ($106), and Delta ($109).

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

    The cheapest flight price from Pensacola to Chicago Midway Airport is $145. On average you can expect to pay $267. 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 Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$329FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$358FlexibilityNo cancel feeOn-timeN/A

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