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$75+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$223
(Southwest)

One-way from

$75
(Cheapflightsfares)

Popular in

July

Cheapest in

April

Average price

$298

Good round-trip deal

$229 or less

Good one-way deal

$194 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. 19% potential increase in price ($86 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 February 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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 4/32:50 pmPNS - MDW
1 stop4h 50mSouthwest
Sat 4/56:10 amMDW - PNS
1 stop4h 50mSouthwest
Deal found 2/19$223
This Delta deal was found by Cheapflights users on 2/18. 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.
Fri 10/311:59 pmPNS - MDW
1 stop4h 04mDelta
Mon 11/33:40 pmMDW - PNS
1 stop5h 01mDelta
Deal found 2/18$239
This Frontier deal was found by Cheapflights users on 2/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/225:36 pmPNS - MDW
1 stop6h 41mFrontier
Mon 2/246:40 amMDW - PNS
1 stop11h 47mFrontier
Deal found 2/18$248

Find flights from Pensacola to Midway within your budget

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 February 20, 2025.

Fly from

Pensacola

Fly to

Midway

Route

Depart

Return

Price

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 4/3

2:50 pm-7:40 pm

1 stop4h 50m

Chicago Midway

Sat 4/5

6:10 am-11:00 am

1 stop4h 50m

$223

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 3/8

6:03 pm-10:20 pm

1 stop4h 17m

Chicago Midway

Tue 3/11

4:59 pm-11:11 pm

1 stop6h 12m

$249

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Fri 6/6

4:35 pm-12:27 am

1 stop7h 52m

Chicago Midway

Mon 6/9

6:15 am-3:34 pm

1 stop9h 19m

$621

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 3/5

5:23 pm-12:17 am

1 stop6h 54m

$75

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Mon 3/24

1:30 pm-3:45 pm

Nonstop2h 15m

$105

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 4/23

5:46 pm-10:26 pm

1 stop4h 40m

$109

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 5/3

12:18 pm-10:18 am

3 stops22h 00m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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 February.
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.

Travel insights for flights from Pensacola to Midway

Get recent, data-driven insights about flights from Pensacola to Midway including ideal travel times, pricing trends, and more.

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 February 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 at noon could potentially save you up to 27% on airfare.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Pensacola to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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
8.1
Very good
4,413 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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
8,227 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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
6.0
Okay
3,358 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

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 $223. Other airlines that can offer you cheap pricing are Delta, from $249, and Frontier, from $621. 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 Frontier ($75), Southwest ($105), 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 $134. On average you can expect to pay $325. The most popular route, (Pensacola - Chicago Midway), can usually be booked for $223.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$207Average$358FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$229Average$368FlexibilityNo cancel feeOn-time63%
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