$124+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Nov 13 — Nov 201
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
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 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 14, 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 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares 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 10/12![Frontier logo]()
$291
This CheapOair deal was found by Cheapflights users on 10/10. 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.
Fri 11/205:40 pm -
1 stop26h 07m
Fri 11/278:42 pm -
1 stop20h 58m
Deal found 10/10![Frontier logo]()
$315
This Delta deal was found by Cheapflights users on 10/13. 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 12/85:44 pm -
1 stop5h 10m
Mon 12/146:00 am -
1 stop5h 12m
Deal found 10/13![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/13. 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.
Tue 12/87:55 am -
2 stops9h 10m
Thu 12/174:00 pm -
1 stop4h 30m
Deal found 10/13![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 10/13. 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.
Tue 12/87:55 am -
2 stops7h 35m
Mon 12/148:50 am -
2 stops9h 15m
Deal found 10/13![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 10/11. 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 12/28:00 am -
1 stop4h 04m
Sun 12/66:00 am -
1 stop6h 44m
Deal found 10/11![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 10/11. 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 12/66:30 am -
2 stops7h 10m
Deal found 10/11![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/13. 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 12/186:00 am -
1 stop8h 55m
Mon 12/217:20 pm -
1 stop4h 00m
Deal found 10/13![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 10/10. 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 10/297:02 am -
1 stop4h 52m
Mon 11/26:04 am -
1 stop4h 48m
Deal found 10/10![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 10/12. 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 11/65:55 pm -
1 stop6h 15m
Thu 11/1212:45 pm -
2 stops7h 50m
Deal found 10/12![Southwest logo]()
$353
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 14, 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 14, 2026.
This Southwest deal was found by Cheapflights users on 10/9. 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 12/112:15 pm -
1 stop6h 35m
Sun 12/135:20 am -
2 stops8h 20m
Deal found 10/9![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 10/11. 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 1/1411:59 am -
1 stop4h 26m
Tue 1/196:00 am -
1 stop6h 51m
Deal found 10/11![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop6h 15m
Mon 11/912:45 pm -
2 stops7h 50m
Deal found 10/14![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 10/10. 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 11/267:05 am -
1 stop9h 15m
Sun 11/295:10 am -
1 stop3h 50m
Deal found 10/10![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 10/10. 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 10/307:55 am -
2 stops7h 00m
Mon 11/212:45 pm -
2 stops7h 45m
Deal found 10/10![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 10/13. 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 12/186:00 am -
2 stops8h 45m
Mon 12/214:20 pm -
2 stops7h 00m
Deal found 10/13![Southwest logo]()
$399
This Southwest deal was found by Cheapflights users on 10/9. 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 12/186:00 am -
1 stop8h 55m
Wed 12/233:40 pm -
1 stop6h 45m
Deal found 10/9![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 10/13. 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.
Sun 2/289:50 am -
1 stop6h 35m
Fri 3/55:00 am -
1 stop9h 25m
Deal found 10/13![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 10/12. 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 10/2411:15 am -
2 stops6h 40m
Sat 10/319:55 am -
1 stop4h 00m
Deal found 10/12![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 10/9. 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 10/286:20 am -
1 stop7h 55m
Wed 11/410:55 am -
2 stops9h 15m
Deal found 10/9![Southwest logo]()
$443
This Southwest deal was found by Cheapflights users on 10/10. 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 10/305:15 pm -
1 stop7h 55m
Sun 11/16:30 am -
2 stops7h 10m
Deal found 10/10![Southwest logo]()
$443
Last-minute flights from Pensacola to MidwayDiscover last-minute flight deals from Pensacola to Midway. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Midway. Data last updated October 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/10. 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 10/297:02 am -
1 stop4h 52m
Mon 11/26:04 am -
1 stop4h 48m
Deal found 10/10![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 10/10. 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 10/297:55 am -
2 stops7h 00m
Mon 11/24:00 pm -
1 stop4h 30m
Deal found 10/10![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 10/10. 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 10/307:02 am -
1 stop4h 52m
Sun 11/16:04 am -
1 stop4h 48m
Deal found 10/10![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:55 pm -
1 stop6h 15m
Mon 11/94:00 pm -
1 stop4h 35m
Deal found 10/14![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 10/12. 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 11/65:55 pm -
1 stop6h 15m
Thu 11/1212:45 pm -
2 stops7h 50m
Deal found 10/12![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:01 am -
1 stop4h 58m
Wed 11/186:00 am -
1 stop6h 40m
Deal found 10/14![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:10 pm -
1 stop6h 35m
Wed 11/1810:55 am -
2 stops9h 15m
Deal found 10/14![Southwest logo]()
$322
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares 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 10/12![Frontier logo]()
$291
This CheapOair deal was found by Cheapflights users on 10/10. 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.
Fri 11/205:40 pm -
1 stop26h 07m
Fri 11/278:42 pm -
1 stop20h 58m
Deal found 10/10![Frontier logo]()
$315
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 14, 2026.
Search for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:30 pm -
1 stop25h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$124
This Priceline deal was found by Cheapflights users on 10/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/112:23 pm -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 1/106:53 pm -
1 stop24h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 10/278:48 am -
2 stops8h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 10/281:25 pm -
2 stops10h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/910:30 am -
2 stops28h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 10/9. 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 11/108:48 am -
2 stops32h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:14 pm -
2 stops21h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$146
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 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Cheapflightsfares) |
One-way from | $124 (Cheapflightsfares) |
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 14, 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
Tue 12/15
7:00 am-12:04 pm
1 stop5h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 1/13
3:55 pm-9:50 pm
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 11/11
7:01 am-11:59 am
1 stop4h 58m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 11/12
7:01 am-11:59 am
1 stop4h 58m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 11/14
5:50 pm-10:54 pm
1 stop5h 04m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 11/3
6:00 am-10:43 am
1 stop4h 43m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/16
6:13 pm-10:54 pm
1 stop4h 41m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
Quickest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 11/10
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 11/17
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Fri 12/11
2:15 pm-8:50 pm
1 stop6h 35m
Chicago Midway
Sun 12/13
5:20 am-1:40 pm
2 stops8h 20m
$333
Showing 1-10 of 20 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 14, 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
Overall
7.9
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
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 14, 2026.
Pensacola and Midway flights
Browse other Pensacola and Midway flight options. Last updated on October 14, 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 14, 2026.
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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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$398 | FlexibilityNo cancel fee | On-time63% |