$155+ Cheap flights from Midway (MDW) to Pensacola (PNS)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Pensacola with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Pensacola
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Cheapest flights from Midway to PensacolaExplore the most affordable flight options available from Midway to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 1, 2026.
Explore the most affordable flight options available from Midway to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/31. 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 9/232:00 pm -
1 stop3h 35m
Tue 9/297:55 am -
1 stop5h 35m
Deal found 8/31![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 8/31. 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 10/216:04 am -
1 stop4h 48m
Thu 10/296:00 am -
1 stop4h 03m
Deal found 8/31![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/28. 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 10/71:05 pm -
2 stops5h 15m
Tue 10/137:55 am -
1 stop5h 30m
Deal found 8/28![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 8/31. 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 10/237:50 am -
2 stops8h 45m
Fri 10/305:15 pm -
1 stop7h 55m
Deal found 8/31![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 8/31. 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 9/266:05 am -
1 stop4h 34m
Tue 9/296:00 am -
1 stop3h 49m
Deal found 8/31![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:30 pm -
1 stop5h 11m
Sun 10/116:00 am -
1 stop4h 03m
Deal found 9/1![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 8/31. 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 9/255:30 am -
1 stop8h 00m
Sun 9/275:55 am -
1 stop4h 00m
Deal found 8/31![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 8/28. 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 11/410:15 am -
1 stop9h 50m
Wed 11/114:10 pm -
1 stop6h 30m
Deal found 8/28![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 10/116:04 am -
1 stop6h 30m
Sat 10/175:40 pm -
1 stop4h 53m
Deal found 8/28![Delta logo]()
$349
Best flights from Midway to PensacolaDiscover carefully curated flight deals from Midway to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
Discover carefully curated flight deals from Midway to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
This Delta deal was found by Cheapflights users on 8/28. 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 10/710:59 am -
1 stop6h 24m
Sun 10/116:00 am -
1 stop4h 03m
Deal found 8/28![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/29. 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 11/24:00 pm -
1 stop4h 30m
Wed 11/44:10 pm -
1 stop3h 50m
Deal found 8/29![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 8/30. 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 10/3011:50 am -
1 stop4h 45m
Mon 11/25:55 pm -
1 stop6h 10m
Deal found 8/30![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 8/30. 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 10/72:10 pm -
1 stop4h 10m
Tue 10/137:55 am -
1 stop5h 30m
Deal found 8/30![Southwest logo]()
$319
Last-minute flights from Midway to PensacolaDiscover last-minute flight deals from Midway to Pensacola. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pensacola. Data last updated September 1, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/31. 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 9/185:55 am -
1 stop7h 10m
Thu 9/244:20 pm -
1 stop6h 05m
Deal found 8/31![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 8/31. 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 9/232:00 pm -
1 stop3h 35m
Tue 9/297:55 am -
1 stop5h 35m
Deal found 8/31![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 8/31. 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 9/255:30 am -
1 stop8h 00m
Sun 9/275:55 am -
1 stop4h 00m
Deal found 8/31![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 8/31. 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 9/266:05 am -
1 stop4h 34m
Tue 9/296:00 am -
1 stop3h 49m
Deal found 8/31![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:30 pm -
1 stop5h 11m
Sun 10/116:00 am -
1 stop4h 03m
Deal found 9/1![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 8/28. 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 10/71:05 pm -
2 stops5h 15m
Tue 10/137:55 am -
1 stop5h 30m
Deal found 8/28![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 8/28. 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.
Sun 10/116:04 am -
1 stop4h 48m
Tue 10/136:00 am -
1 stop5h 54m
Deal found 8/28![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/31. 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 10/216:04 am -
1 stop6h 30m
Tue 10/276:00 am -
1 stop5h 54m
Deal found 8/31![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/31. 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 10/237:50 am -
2 stops8h 45m
Fri 10/305:15 pm -
1 stop7h 55m
Deal found 8/31![Southwest logo]()
$330
One-way flights from Midway to PensacolaSearch for one-way flight options from Midway to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Midway to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/30. 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 9/292:00 pm -
1 stop3h 35m
Deal found 8/30![Southwest logo]()
$155
This Delta deal was found by Cheapflights users on 8/28. 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 9/305:11 pm -
1 stop6h 10m
Deal found 8/28![Delta logo]()
$160
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:55 am -
1 stop3h 35m
Deal found 9/1![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Mon 9/286:46 pm -
2 stops17h 54m
Deal found 8/31![Multiple Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:04 am -
1 stop6h 30m
Deal found 9/1![Delta logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Sat 9/266:25 am -
2 stops25h 13m
Deal found 8/28![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Mon 10/266:15 am -
2 stops25h 53m
Deal found 8/27![Multiple Airlines logo]()
$175
This Delta deal was found by Cheapflights users on 8/28. 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 9/166:05 am -
1 stop6h 34m
Deal found 8/28![Delta logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/286:16 am -
2 stops25h 22m
Deal found 8/27![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Tue 9/296:25 am -
2 stops25h 53m
Deal found 8/30![Multiple Airlines logo]()
$184
Find flight deals from Midway to Pensacola
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pensacola (PNS). 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 September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $314 (Southwest) |
One-way from | $155 (Southwest) |
Popular in | March |
Cheapest in | November |
Average price | $365 |
Good one-way deal | $395 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Pensacola 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 7,457,451 searches. Data last updated September 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 10/7
10:59 am-5:23 pm
1 stop6h 24m
Pensacola
Sun 10/11
6:00 am-10:03 am
1 stop4h 03m
$319
Quickest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Mon 11/2
4:00 pm-8:30 pm
1 stop4h 30m
Pensacola
Wed 11/4
4:10 pm-8:00 pm
1 stop3h 50m
$319
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Fri 10/30
11:50 am-4:35 pm
1 stop4h 45m
Pensacola
Mon 11/2
5:55 pm-12:05 am
1 stop6h 10m
$319
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 10/7
2:10 pm-6:20 pm
1 stop4h 10m
Pensacola
Tue 10/13
7:55 am-1:25 pm
1 stop5h 30m
$319
Cheapest one-way
Quickest one-way
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 9/30
2:45 pm-6:40 pm
1 stop3h 55m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Fri 9/25
6:05 am-12:39 pm
1 stop6h 34m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Thu 10/1
1:00 pm-7:09 pm
1 stop6h 09m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sat 9/26
6:05 am-10:39 am
1 stop4h 34m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 10/27
5:09 pm-11:30 pm
1 stop6h 21m
$160
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 9/29
10:48 am-3:02 pm
1 stop4h 14m
$160
Showing 1-10 of 15 resultsSorted by cheapest first
Compare providers for flights from Midway to Pensacola
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 Midway to Pensacola in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pensacola flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Pensacola 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 Chicago Midway Airport-Pensacola 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 Midway to Pensacola
Have a flexible travel schedule? Discover the best time to fly to Pensacola from Midway with our price prediction graph.
MDW-PNS
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 Chicago Midway Airport to Pensacola
What is the cheapest month to book a flight from Chicago Midway Airport to Pensacola?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $132). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $493). 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.
How much does it cost to fly round-trip from Chicago Midway Airport to Pensacola?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Pensacola flights typically cost between $341 and $389 in September.The cheapest round-trip price found within the last 5 days was $314 on Southwest (Sep 23-Sep 29).
Reviews of airlines servicing Pensacola
Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated September 1, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Pensacola, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Midway to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Pensacola?
Book flights to Pensacola if you plan to visit one of these locationsNavarre
Gulf Breeze
Foley
Navarre Beach
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Midway and Pensacola flights
Browse other Midway and Pensacola flight options. Last updated on September 1, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
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Explore flights to Pensacola departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Midway to Pensacola
Discover the top 2 airlines that operate flights from Midway to Pensacola. 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 7,457,451 searches. Data last updated September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$311 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$397 | FlexibilityNo cancel fee | On-time63% |