$126+ Cheap flights from Midway (MDW) to Pensacola (PNS)
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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PNS
Nov 13 — Nov 201
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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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 October 14, 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 October 14, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:05 pm -
1 stop4h 48m
Mon 11/166:13 pm -
1 stop4h 41m
Deal found 10/9![Delta logo]()
$317
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/124:08 pm -
1 stop6h 04m
Sun 12/205:59 pm -
1 stop4h 23m
Deal found 10/12![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 11/1110:55 am -
2 stops9h 15m
Wed 11/187:55 am -
1 stop5h 00m
Deal found 10/11![Southwest logo]()
$333
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.
Fri 12/188:07 pm -
1 stop19h 11m
Mon 12/2812:23 pm -
1 stop6h 39m
Deal found 10/13![Frontier logo]()
$337
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 12/126:00 am -
2 stops10h 20m
Sun 12/206:20 pm -
1 stop5h 55m
Deal found 10/12![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 10/296:04 am -
1 stop6h 30m
Mon 11/25:40 pm -
1 stop4h 53m
Deal found 10/10![Delta logo]()
$348
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:43 pm -
1 stop18h 25m
Tue 12/87:05 pm -
2 stops16h 28m
Deal found 10/12![Multiple Airlines logo]()
$350
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:43 pm -
1 stop18h 25m
Mon 12/77:46 pm -
2 stops15h 47m
Deal found 10/12![Multiple Airlines logo]()
$352
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 11/126:00 am -
1 stop6h 40m
Sun 11/156:00 am -
1 stop4h 24m
Deal found 10/11![Delta logo]()
$359
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 October 14, 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 October 14, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:05 pm -
1 stop4h 03m
Mon 11/166:13 pm -
1 stop4h 41m
Deal found 10/12![Delta logo]()
$317
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.
Mon 2/227:10 am -
2 stops8h 15m
Mon 3/17:55 am -
2 stops5h 50m
Deal found 10/11![Southwest logo]()
$338
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/116:00 am -
1 stop4h 47m
Tue 3/1611:59 am -
1 stop4h 26m
Deal found 10/12![Delta logo]()
$339
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.
Thu 2/115:00 am -
1 stop9h 25m
Sun 2/147:55 am -
2 stops6h 55m
Deal found 10/9![Southwest logo]()
$378
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.
Thu 1/1410:05 am -
2 stops8h 05m
Sun 1/177:55 am -
2 stops6h 55m
Deal found 10/9![Southwest logo]()
$388
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.
Tue 12/224:20 pm -
2 stops7h 00m
Fri 1/17:55 am -
1 stop5h 00m
Deal found 10/12![Southwest logo]()
$403
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 12/227:20 pm -
1 stop4h 00m
Sat 12/263:35 pm -
1 stop7h 30m
Deal found 10/13![Southwest logo]()
$417
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 10/255:00 am -
1 stop5h 25m
Fri 10/3010:30 am -
1 stop4h 35m
Deal found 10/13![Southwest logo]()
$434
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 11/1310:15 am -
2 stops7h 05m
Mon 11/164:10 pm -
1 stop6h 35m
Deal found 10/9![Southwest logo]()
$446
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.
Thu 11/1910:55 am -
2 stops9h 15m
Mon 11/235:25 am -
2 stops6h 35m
Deal found 10/12![Southwest logo]()
$467
Last-minute flights from Midway to PensacolaDiscover last-minute flight deals from Midway to Pensacola. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pensacola. Data last updated October 14, 2026 and is based on user searches.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:04 am -
1 stop4h 48m
Thu 10/2911:58 am -
1 stop4h 16m
Deal found 10/9![Delta logo]()
$379
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.
Sun 10/255:00 am -
1 stop5h 25m
Thu 10/296:05 pm -
2 stops7h 05m
Deal found 10/9![Southwest logo]()
$384
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 10/296:04 am -
1 stop6h 30m
Mon 11/25:40 pm -
1 stop4h 53m
Deal found 10/10![Delta logo]()
$348
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.
Fri 10/3011:05 am -
2 stops5h 30m
Mon 11/25:55 pm -
1 stop6h 10m
Deal found 10/11![Southwest logo]()
$364
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:05 pm -
1 stop4h 48m
Mon 11/166:13 pm -
1 stop4h 41m
Deal found 10/9![Delta logo]()
$317
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 11/1110:55 am -
2 stops9h 15m
Wed 11/187:55 am -
1 stop5h 00m
Deal found 10/11![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 11/126:00 am -
1 stop6h 40m
Sun 11/156:00 am -
1 stop4h 24m
Deal found 10/11![Delta logo]()
$359
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:27 am -
1 stop6h 05m
Mon 11/166:13 pm -
1 stop4h 41m
Deal found 10/12![Delta logo]()
$388
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.
Thu 11/197:05 am -
1 stop8h 30m
Mon 11/235:55 pm -
1 stop6h 15m
Deal found 10/12![Southwest logo]()
$372
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:08 am -
2 stops13h 11m
Mon 11/236:30 pm -
1 stop25h 17m
Deal found 10/12![Frontier logo]()
$374
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 October 14, 2026.
Search for one-way flight options from Midway to Pensacola. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:42 pm -
1 stop20h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$126
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:37 pm -
1 stop18h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$129
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/139:37 pm -
1 stop18h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Mon 1/111:18 pm -
2 stops24h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$134
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.
Fri 12/113:50 pm -
2 stops18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$139
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop20h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$143
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 12/812:28 pm -
2 stops24h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![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.
Wed 12/912:28 pm -
2 stops19h 10m
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 12/143:50 pm -
2 stops16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$146
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.
Sun 12/133:50 pm -
2 stops16h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$147
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.
Mon 12/73:50 pm -
2 stops16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$148
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 October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Southwest) |
One-way from | $126 (Travelocity) |
Popular in | March |
Cheapest in | November |
Average price | $365 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Pensacola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 14, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 12/9
6:00 am-11:12 am
1 stop5h 12m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Fri 1/8
5:25 pm-11:27 pm
1 stop6h 02m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
Quickest round-trip
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 11/10
1:05 pm-5:53 pm
1 stop4h 48m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Thu 12/10
6:00 am-11:12 am
1 stop5h 12m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Sat 11/21
5:13 pm-10:13 pm
1 stop5h 00m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 1/6
5:25 pm-11:27 pm
1 stop6h 02m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Tue 12/8
1:02 pm-5:57 pm
1 stop4h 55m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Wed 11/11
6:00 am-12:40 pm
1 stop6h 40m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Mon 1/11
5:25 pm-11:27 pm
1 stop6h 02m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
ChicagoPensacola
MDW Chicago Midway - PNS Pensacola
MDWPNS
Chicago Midway
Thu 1/7
6:00 am-12:51 pm
1 stop6h 51m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Pensacola flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Pensacola flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Pensacola flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Pensacola
Have a flexible travel schedule? Discover the best time to fly to Pensacola from Midway with our price prediction graph.
MDW-PNS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Pensacola
What is the cheapest month to book a flight from Chicago Midway Airport to Pensacola?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Pensacola (average of $132). Flying from Chicago Midway Airport to Pensacola in March is currently the most expensive (average of $493). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Chicago Midway Airport to Pensacola?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Pensacola flights typically cost between $353 and $410 in January.The cheapest round-trip price found within the last 5 days was $317 on Southwest (Jan 27-Jan 30).
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 October 14, 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
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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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.
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Book flights to Pensacola if you plan to visit one of these locationsAtmore
Navarre
Gulf Breeze
Foley
Navarre Beach
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Top 2 airlines flying from Midway to Pensacola
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$324 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$278 | Average$397 | FlexibilityNo cancel fee | On-time63% |