$96+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Sep 16 — Sep 231
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 August 17, 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 August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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 9/92:00 pm -
1 stop3h 35m
Wed 9/166:15 pm -
1 stop3h 40m
Deal found 8/13![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 8/12. 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
Sat 10/36:00 am -
1 stop4h 36m
Deal found 8/12![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/266:45 am -
1 stop5h 05m
Sat 10/37:45 am -
2 stops7h 05m
Deal found 8/12![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 8/13. 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 10/26:05 pm -
1 stop4h 45m
Mon 10/56:05 pm -
1 stop5h 50m
Deal found 8/13![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 8/12. 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 9/185:30 am -
1 stop7h 00m
Thu 9/242:40 pm -
2 stops8h 45m
Deal found 8/12![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 8/12. 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 9/12:00 pm -
1 stop3h 35m
Fri 9/44:20 pm -
1 stop6h 05m
Deal found 8/12![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 8/12. 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 9/117:30 am -
1 stop6h 35m
Fri 9/1812:45 pm -
1 stop6h 10m
Deal found 8/12![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 11/105:09 pm -
1 stop6h 22m
Sun 11/156:00 am -
1 stop4h 33m
Deal found 8/13![Delta logo]()
$249
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 August 17, 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 August 17, 2026.
This Delta deal was found by Cheapflights users on 8/12. 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 11/66:04 am -
1 stop6h 30m
Mon 11/94:17 pm -
1 stop6h 39m
Deal found 8/12![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/16. 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 9/302:00 pm -
1 stop3h 35m
Wed 10/74:10 pm -
1 stop6h 00m
Deal found 8/16![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/12. 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 10/21:00 pm -
1 stop3h 46m
Tue 10/67:02 am -
1 stop4h 48m
Deal found 8/12![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/15. 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.
Sat 9/266:35 am -
1 stop3h 35m
Mon 9/281:45 pm -
1 stop6h 25m
Deal found 8/15![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/15. 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 9/299:00 am -
2 stops8h 35m
Tue 10/64:10 pm -
2 stops7h 35m
Deal found 8/15![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 8/16. 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 9/185:55 am -
1 stop7h 10m
Sun 9/207:50 am -
2 stops6h 00m
Deal found 8/16![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 8/16. 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 10/712:00 pm -
2 stops8h 10m
Sat 10/107:45 am -
2 stops7h 05m
Deal found 8/16![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 8/16. 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.
Thu 11/198:50 am -
1 stop6h 45m
Tue 11/246:20 pm -
1 stop5h 55m
Deal found 8/16![Southwest logo]()
$377
Last-minute flights from Midway to PensacolaDiscover last-minute flight deals from Midway to Pensacola. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pensacola. Data last updated August 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/12. 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 9/12:00 pm -
1 stop3h 35m
Fri 9/44:20 pm -
1 stop6h 05m
Deal found 8/12![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/12. 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 9/210:54 am -
1 stop3h 57m
Wed 9/95:30 pm -
1 stop5h 14m
Deal found 8/12![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 8/12. 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 9/117:30 am -
1 stop6h 35m
Fri 9/1812:45 pm -
1 stop6h 10m
Deal found 8/12![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 8/12. 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 9/124:30 pm -
1 stop5h 11m
Thu 9/176:00 am -
1 stop3h 49m
Deal found 8/12![Delta logo]()
$224
This Southwest deal was found by Cheapflights users on 8/12. 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 9/162:00 pm -
1 stop3h 35m
Wed 9/234:20 pm -
1 stop3h 50m
Deal found 8/12![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/12. 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 9/162:00 pm -
1 stop3h 35m
Tue 9/227:55 am -
2 stops7h 30m
Deal found 8/12![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 8/12. 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 9/185:30 am -
1 stop7h 00m
Thu 9/242:40 pm -
2 stops8h 45m
Deal found 8/12![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 8/12. 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
Sat 10/36:00 am -
1 stop4h 36m
Deal found 8/12![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/266:45 am -
1 stop5h 05m
Sat 10/37:45 am -
2 stops7h 05m
Deal found 8/12![Southwest logo]()
$205
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 August 17, 2026.
Search for one-way flight options from Midway to Pensacola. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/12. 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 9/22:00 pm -
1 stop3h 35m
Deal found 8/12![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 8/13. 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 9/124:30 pm -
1 stop5h 11m
Deal found 8/13![Delta logo]()
$100
This Delta deal was found by Cheapflights users on 8/13. 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 9/1111:35 am -
1 stop5h 36m
Deal found 8/13![Delta logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/156:25 am -
2 stops30h 20m
Deal found 8/12![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/146:46 pm -
2 stops17h 54m
Deal found 8/12![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
2 stops30h 49m
Deal found 8/16![Frontier logo]()
$142
This Southwest deal was found by Cheapflights users on 8/16. 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.
Tue 9/152:00 pm -
1 stop3h 35m
Deal found 8/16![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/146:15 am -
2 stops25h 23m
Deal found 8/14![Multiple Airlines logo]()
$146
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $195 (Southwest) |
One-way from | $96 (Southwest) |
Popular in | March |
Cheapest in | November |
Average price | $376 |
Good round-trip deal | $477 or less |
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 2,558,603 searches. Data last updated August 17, 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
Fri 11/6
6:04 am-12:34 pm
1 stop6h 30m
Pensacola
Mon 11/9
4:17 pm-10:56 pm
1 stop6h 39m
$249
Quickest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Fri 10/2
1:00 pm-4:46 pm
1 stop3h 46m
Pensacola
Tue 10/6
7:02 am-11:50 am
1 stop4h 48m
$249
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 9/30
2:00 pm-5:35 pm
1 stop3h 35m
Pensacola
Wed 10/7
4:10 pm-10:10 pm
1 stop6h 00m
$294
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sat 9/26
6:35 am-10:10 am
1 stop3h 35m
Pensacola
Mon 9/28
1:45 pm-8:10 pm
1 stop6h 25m
$299
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 9/29
9:00 am-5:35 pm
2 stops8h 35m
Pensacola
Tue 10/6
4:10 pm-11:45 pm
2 stops7h 35m
$309
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Fri 9/18
5:55 am-1:05 pm
1 stop7h 10m
Pensacola
Sun 9/20
7:50 am-1:50 pm
2 stops6h 00m
$349
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 10/7
12:00 pm-8:10 pm
2 stops8h 10m
Pensacola
Sat 10/10
7:45 am-2:50 pm
2 stops7h 05m
$368
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Thu 11/19
8:50 am-3:35 pm
1 stop6h 45m
Pensacola
Tue 11/24
6:20 pm-12:15 am
1 stop5h 55m
$377
Cheapest one-way
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 11/11
6:00 am-12:39 pm
1 stop6h 39m
$100
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sat 11/14
4:19 pm-10:04 pm
1 stop5h 45m
$100
Showing 1-10 of 16 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 August.
| 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
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 August 17, 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.
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
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 locationsGulf Breeze
Navarre
Foley
Navarre Beach
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Midway and Pensacola flights
Browse other Midway and Pensacola flight options. Last updated on August 17, 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 August 17, 2026.
Other flights to Pensacola
Explore flights to Pensacola departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 17, 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$385 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$311 | FlexibilityNo cancel fee | On-timeN/A |