$104+ Cheap flights from Pensacola (PNS) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Nov 23 — Nov 301
Round-trip
1 adult, Economy
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Find cheap flights from Pensacola to Midway 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
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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 Pensacola to Midway
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Cheapest flights from Pensacola to MidwayExplore 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 October 24, 2026.
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 October 24, 2026.
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:01 pm -
1 stop21h 29m
Tue 12/228:35 pm -
1 stop20h 47m
Deal found 10/20![Frontier logo]()
$219
This Southwest deal was found by Cheapflights users on 10/20. 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 11/216:25 pm -
1 stop6h 00m
Sat 12/56:00 am -
1 stop6h 50m
Deal found 10/20![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 10/23. 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 12/36:20 am -
2 stops8h 00m
Mon 12/79:55 am -
1 stop8h 15m
Deal found 10/23![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 10/22. 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 11/117:55 am -
1 stop5h 00m
Wed 11/1812:45 pm -
1 stop5h 25m
Deal found 10/22![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 10/22. 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 12/115:55 pm -
1 stop6h 15m
Tue 12/158:50 am -
1 stop6h 45m
Deal found 10/22![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 10/21. 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 12/24:10 pm -
1 stop6h 35m
Sun 12/68:00 am -
1 stop5h 40m
Deal found 10/21![Southwest logo]()
$267
Best flights from Pensacola to MidwayDiscover carefully curated flight deals from Pensacola to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 24, 2026.
Discover carefully curated flight deals from Pensacola to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 24, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 12/26:20 am -
1 stop6h 05m
Wed 12/98:50 am -
1 stop6h 45m
Deal found 10/22![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:59 am -
1 stop4h 17m
Mon 12/76:00 am -
1 stop6h 44m
Deal found 10/19![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/22. 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 11/117:55 am -
2 stops6h 35m
Wed 11/1812:45 pm -
1 stop5h 25m
Deal found 10/22![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/196:00 am -
1 stop4h 24m
Thu 11/264:13 pm -
1 stop5h 51m
Deal found 10/21![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sun 12/135:25 am -
1 stop4h 55m
Thu 12/175:05 am -
2 stops8h 35m
Deal found 10/22![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 10/23. 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.
Thu 12/314:45 pm -
1 stop5h 37m
Tue 1/56:00 am -
1 stop4h 47m
Deal found 10/23![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 10/23. 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 12/236:20 pm -
1 stop6h 00m
Mon 12/284:20 pm -
2 stops7h 05m
Deal found 10/23![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 10/24. 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.
Thu 11/126:00 am -
1 stop4h 24m
Sun 11/155:13 pm -
1 stop6h 28m
Deal found 10/24![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 10/21. 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 11/132:15 pm -
1 stop6h 35m
Sun 11/154:00 pm -
1 stop4h 35m
Deal found 10/21![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 10/22. 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 11/147:40 am -
2 stops7h 10m
Sun 11/154:00 pm -
1 stop4h 35m
Deal found 10/22![Southwest logo]()
$432
Last-minute flights from Pensacola to MidwayDiscover last-minute flight deals from Pensacola to Midway. Data last updated October 24, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Midway. Data last updated October 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/22. 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 11/117:55 am -
1 stop5h 00m
Wed 11/1812:45 pm -
1 stop5h 25m
Deal found 10/22![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 10/20. 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 11/194:10 pm -
1 stop6h 35m
Thu 11/267:30 am -
2 stops8h 00m
Deal found 10/20![Southwest logo]()
$247
This CheapOair deal was found by Cheapflights users on 10/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:14 pm -
1 stop23h 33m
Sun 11/228:42 pm -
1 stop20h 53m
Deal found 10/19![Frontier logo]()
$290
This Trip.com deal was found by Cheapflights users on 10/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:40 pm -
1 stop26h 07m
Sun 11/228:42 pm -
1 stop20h 53m
Deal found 10/21![Frontier logo]()
$273
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 11/205:55 pm -
1 stop6h 15m
Sat 12/56:00 am -
1 stop6h 50m
Deal found 10/19![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/20. 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 11/216:25 pm -
1 stop6h 00m
Sat 12/56:00 am -
1 stop6h 50m
Deal found 10/20![Southwest logo]()
$236
One-way flights from Pensacola to MidwaySearch for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
Search for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
This Super.com deal was found by Cheapflights users on 10/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:01 pm -
1 stop21h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 10/21. 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 11/146:00 am -
2 stops6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$123
This Super.com deal was found by Cheapflights users on 10/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:14 pm -
1 stop23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/97:46 pm -
2 stops22h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 11/1912:45 pm -
2 stops11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 10/19. 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.
Mon 11/95:55 pm -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/196:07 pm -
3 stops25h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/158:14 pm -
2 stops39h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$188
This Delta deal was found by Cheapflights users on 10/22. 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 12/305:59 pm -
1 stop4h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$190
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 October 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (Trip.com) |
One-way from | $104 (Super.com) |
Popular in | August |
Cheapest in | June |
Average price | $448 |
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 7,457,451 searches. Data last updated October 24, 2026.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 12/19
5:25 pm-12:45 am
2 stops7h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 11/14
6:00 am-12:55 pm
2 stops6h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/9
7:46 pm-5:47 pm
2 stops22h 01m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$137
Quickest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 12/30
5:59 pm-10:22 pm
1 stop4h 23m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/9
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 11/5
5:40 pm-10:33 pm
1 stop4h 53m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$225
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 12/2
6:20 am-12:25 pm
1 stop6h 05m
Chicago Midway
Wed 12/9
8:50 am-3:35 pm
1 stop6h 45m
$236
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Fri 1/1
7:55 am-2:30 pm
2 stops6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/9
2:15 pm-11:15 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 11/3
7:55 am-3:30 pm
2 stops7h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
Showing 1-10 of 19 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
PNS-MDW
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.
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 October 24, 2026.
See what other customers who have flown with Southwest 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.
Boarding
8.1
Entertainment
7.4
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Entertainment
7.4
Crew
8.6
Comfort
8.0
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 24, 2026.
Pensacola and Midway flights
Browse other Pensacola and Midway flight options. Last updated on October 24, 2026.
Other flights from Pensacola
Browse through other flights departing from Pensacola. Flights are based on user searches made on Cheapflights and were last updated on October 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Pensacola to Midway
Discover the top airline 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 7,457,451 searches. Data last updated October 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$398 | FlexibilityNo cancel fee | On-time63% |