$137+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Jun 11 — Jun 181
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
Cheapest
Best
Last-minute
One-way
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 May 12, 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 May 12, 2026.
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 6/912:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Tue 6/163:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/10![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 5/8. 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 6/1012:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Sat 6/133:50 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 5/8. 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 6/47:45 am
MDW
- PNS
Nonstop2h 15m
Southwest
Mon 6/810:40 am
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 5/11. 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 6/1712:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Sat 7/410:00 am
PNS
- MDW
1 stop4h 55m
Southwest
Deal found 5/11![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/28:00 am
MDW
- PNS
1 stop6h 05m
Southwest
Wed 6/103:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/11![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 9/221:55 pm
MDW
- PNS
1 stop3h 30m
Southwest
Tue 9/294:20 pm
PNS
- MDW
1 stop3h 50m
Southwest
Deal found 5/11![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 6/272:35 pm
MDW
- PNS
1 stop6h 00m
Southwest
Sat 7/412:50 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/11![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 5/11. 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.
Tue 9/225:25 pm
MDW
- PNS
1 stop4h 36m
Delta
Tue 9/298:00 am
PNS
- MDW
1 stop3h 54m
Delta
Deal found 5/11![Delta logo]()
$369
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 May 12, 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 May 12, 2026.
This Southwest deal was found by Cheapflights users on 5/11. 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 6/312:15 pm
MDW
- PNS
1 stop8h 05m
Southwest
Wed 6/103:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/11![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 5/8. 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 6/47:45 am
MDW
- PNS
Nonstop2h 15m
Southwest
Mon 6/87:00 am
PNS
- MDW
2 stops8h 55m
Southwest
Deal found 5/8![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 5/9. 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.
Sun 5/248:50 am
MDW
- PNS
Nonstop2h 15m
Southwest
Thu 5/287:15 am
PNS
- MDW
2 stops7h 50m
Southwest
Deal found 5/9![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 5/11. 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.
Fri 5/297:50 am
MDW
- PNS
2 stops7h 50m
Southwest
Tue 6/27:40 am
PNS
- MDW
2 stops9h 15m
Southwest
Deal found 5/11![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 5/7. 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 7/237:45 am
MDW
- PNS
Nonstop2h 15m
Southwest
Tue 7/283:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 5/7. 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 6/46:40 am
MDW
- PNS
1 stop6h 50m
Southwest
Sun 6/75:35 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/7![Southwest logo]()
$405
This Southwest deal was found by Cheapflights users on 5/7. 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 6/227:45 am
MDW
- PNS
Nonstop2h 15m
Southwest
Sat 6/276:30 pm
PNS
- MDW
1 stop4h 45m
Southwest
Deal found 5/7![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 5/8. 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 6/1012:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Fri 6/1211:05 am
PNS
- MDW
2 stops8h 00m
Southwest
Deal found 5/8![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 5/8. 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 7/22:05 pm
MDW
- PNS
2 stops7h 30m
Southwest
Tue 7/73:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$408
Last-minute flights from Midway to PensacolaDiscover last-minute flight deals from Midway to Pensacola. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pensacola. Data last updated May 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/11. 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.
Tue 6/28:00 am
MDW
- PNS
1 stop6h 05m
Southwest
Wed 6/103:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/11![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 5/11. 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 6/312:53 pm
MDW
- PNS
1 stop4h 18m
Delta
Wed 6/106:00 am
PNS
- MDW
1 stop4h 09m
Delta
Deal found 5/11![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 5/8. 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 6/47:45 am
MDW
- PNS
Nonstop2h 15m
Southwest
Mon 6/810:40 am
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 5/10. 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.
Tue 6/912:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Tue 6/163:45 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/10![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 5/8. 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 6/1012:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Sat 6/133:50 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/8![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 5/11. 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 6/1712:55 pm
MDW
- PNS
Nonstop2h 10m
Southwest
Sat 7/410:00 am
PNS
- MDW
1 stop4h 55m
Southwest
Deal found 5/11![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sat 6/272:35 pm
MDW
- PNS
1 stop6h 00m
Southwest
Sat 7/412:50 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 5/11![Southwest logo]()
$365
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 May 12, 2026.
Search for one-way flight options from Midway to Pensacola. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
MDW
- PNS
2 stops26h 01m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 6/212:27 pm
MDW
- PNS
2 stops21h 19m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 9/212:04 pm
MDW
- PNS
2 stops25h 55m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/96:00 am
MDW
- PNS
2 stops27h 46m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 7/86:00 am
MDW
- PNS
2 stops36h 58m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- PNS
2 stops25h 55m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:11 pm
MDW
- PNS
2 stops21h 35m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Wed 6/1012:04 pm
MDW
- PNS
2 stops18h 57m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 7/16:00 am
MDW
- PNS
2 stops36h 58m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$170
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 May 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (Southwest) |
One-way from | $137 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $392 |
Good round-trip deal | $412 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 May 12, 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 - PNS
MDWPNS
Chicago Midway
Wed 6/3
12:15 pm-8:20 pm
1 stop8h 05m
Pensacola
Wed 6/10
3:45 pm-6:00 pm
Nonstop2h 15m
$359
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 6/4
7:45 am-10:00 am
Nonstop2h 15m
Pensacola
Mon 6/8
7:00 am-3:55 pm
2 stops8h 55m
$368
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sun 5/24
8:50 am-11:05 am
Nonstop2h 15m
Pensacola
Thu 5/28
7:15 am-3:05 pm
2 stops7h 50m
$370
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Fri 5/29
7:50 am-3:40 pm
2 stops7h 50m
Pensacola
Tue 6/2
7:40 am-4:55 pm
2 stops9h 15m
$382
Quickest round-trip
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 7/23
7:45 am-10:00 am
Nonstop2h 15m
Pensacola
Tue 7/28
3:45 pm-6:00 pm
Nonstop2h 15m
$393
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 6/4
6:40 am-1:30 pm
1 stop6h 50m
Pensacola
Sun 6/7
5:35 pm-7:50 pm
Nonstop2h 15m
$405
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Mon 6/22
7:45 am-10:00 am
Nonstop2h 15m
Pensacola
Sat 6/27
6:30 pm-11:15 pm
1 stop4h 45m
$406
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 6/10
12:55 pm-3:05 pm
Nonstop2h 10m
Pensacola
Fri 6/12
11:05 am-7:05 pm
2 stops8h 00m
$408
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 7/2
2:05 pm-9:35 pm
2 stops7h 30m
Pensacola
Tue 7/7
3:45 pm-6:00 pm
Nonstop2h 15m
$408
Cheapest one-way
Quickest one-way
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Tue 7/7
12:55 pm-3:05 pm
Nonstop2h 10m
$175
Showing 1-10 of 20 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 May.
| 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 time of day to fly from MDW to PNS?
Find hourly flight availability from Midway to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Pensacola as you normally would.
How much does it cost to fly round-trip 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 May 12, 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.
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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
Perdido Key
Warrington
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Midway and Pensacola flights
Browse other Midway and Pensacola flight options. Last updated on May 12, 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 May 12, 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 May 12, 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 May 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$376 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$227 | Average$298 | FlexibilityNo cancel fee | On-timeN/A |