$140+ Cheap flights from Pensacola (PNS) to Midway (MDW)
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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Sep 4 — Sep 111
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 August 5, 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 August 5, 2026.
This Southwest deal was found by Cheapflights users on 8/1. 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 9/65:55 pm -
1 stop5h 00m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/1![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 8/4. 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 9/14:20 pm -
1 stop6h 00m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/4![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/1. 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 9/16:00 am -
1 stop3h 59m
Sat 9/54:39 pm -
1 stop4h 58m
Deal found 8/1![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 8/4. 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 10/15:15 pm -
1 stop7h 50m
Tue 10/66:00 am -
1 stop7h 00m
Deal found 8/4![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:20 pm -
1 stop6h 05m
Sun 9/68:35 am -
1 stop8h 25m
Deal found 8/4![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 8/5. 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 9/31:10 pm -
1 stop6h 10m
Tue 9/81:00 pm -
2 stops5h 40m
Deal found 8/5![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/4. 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 9/144:20 pm -
1 stop3h 50m
Thu 9/175:55 am -
1 stop7h 10m
Deal found 8/4![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 7/31. 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 8/204:20 pm -
1 stop3h 50m
Mon 8/245:30 am -
1 stop7h 00m
Deal found 7/31![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 8/1. 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 8/227:05 am -
2 stops9h 35m
Mon 8/245:30 am -
2 stops7h 35m
Deal found 8/1![Southwest logo]()
$320
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 August 5, 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 August 5, 2026.
This Southwest deal was found by Cheapflights users on 8/1. 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 9/65:55 pm -
1 stop5h 00m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/1![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 8/2. 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 10/15:51 pm -
1 stop4h 53m
Sat 10/34:30 pm -
1 stop5h 11m
Deal found 8/2![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:40 am -
1 stop4h 40m
Sat 9/266:45 am -
1 stop5h 05m
Deal found 8/4![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/5. 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 9/206:00 am -
1 stop3h 49m
Tue 9/221:00 pm -
1 stop4h 11m
Deal found 8/5![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/2. 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 8/299:40 am -
1 stop4h 40m
Mon 8/315:30 am -
1 stop8h 00m
Deal found 8/2![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 7/31. 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 9/294:20 pm -
1 stop3h 50m
Tue 10/68:05 am -
1 stop3h 55m
Deal found 7/31![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/4. 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 9/31:10 pm -
1 stop6h 10m
Thu 9/105:30 am -
1 stop7h 00m
Deal found 8/4![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/3. 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 9/31:10 pm -
1 stop8h 50m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/3![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/31. 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 9/102:40 pm -
2 stops8h 45m
Tue 9/152:00 pm -
1 stop3h 35m
Deal found 7/31![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 8/4. 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 9/13:00 pm -
2 stops8h 10m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/4![Southwest logo]()
$300
Last-minute flights from Pensacola to MidwayDiscover last-minute flight deals from Pensacola to Midway. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Midway. Data last updated August 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/31. 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 8/204:20 pm -
1 stop3h 50m
Mon 8/245:30 am -
1 stop7h 00m
Deal found 7/31![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 8/1. 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 8/227:05 am -
2 stops9h 35m
Mon 8/245:30 am -
2 stops7h 35m
Deal found 8/1![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 7/31. 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 8/308:06 am -
1 stop3h 45m
Tue 9/16:05 am -
1 stop4h 38m
Deal found 7/31![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/4. 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 9/14:20 pm -
1 stop6h 00m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/4![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/1. 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 9/16:00 am -
1 stop3h 59m
Sat 9/54:39 pm -
1 stop4h 58m
Deal found 8/1![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 8/4. 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 9/31:10 pm -
1 stop6h 10m
Thu 9/1012:30 pm -
2 stops7h 35m
Deal found 8/4![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/3. 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 9/31:10 pm -
1 stop8h 50m
Tue 9/81:00 pm -
2 stops5h 40m
Deal found 8/3![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:20 pm -
1 stop6h 05m
Sun 9/68:35 am -
1 stop8h 25m
Deal found 8/4![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 8/1. 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 9/65:55 pm -
1 stop5h 00m
Tue 9/82:00 pm -
1 stop3h 35m
Deal found 8/1![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 8/4. 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 9/144:20 pm -
1 stop3h 50m
Thu 9/175:30 am -
2 stops7h 35m
Deal found 8/4![Southwest 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 August 5, 2026.
Search for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/217:32 pm -
2 stops27h 15m
Deal found 7/31![Multiple Airlines logo]()
$140
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:40 am -
1 stop4h 40m
Deal found 8/4![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 9/307:35 pm -
2 stops22h 11m
Deal found 7/31![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 10/112:45 pm -
2 stops10h 59m
Deal found 8/2![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:25 pm -
2 stops28h 21m
Deal found 7/31![Multiple Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 pm -
1 stop5h 36m
Deal found 8/4![Delta logo]()
$149
This Southwest deal was found by Cheapflights users on 8/3. 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 10/25:15 pm -
1 stop7h 50m
Deal found 8/3![Southwest logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 11/13:15 pm -
2 stops30h 38m
Deal found 8/1![Frontier logo]()
$154
This Southwest deal was found by Cheapflights users on 8/1. 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 8/242:40 pm -
2 stops8h 40m
Deal found 8/1![Southwest logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 9/27:33 pm -
2 stops27h 14m
Deal found 8/4![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/287:32 pm -
2 stops27h 15m
Deal found 8/1![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/47:32 pm -
2 stops27h 15m
Deal found 8/3![Multiple Airlines logo]()
$158
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 August 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $293 (Southwest) |
One-way from | $140 (Kiwi.com) |
Popular in | March |
Cheapest in | June |
Average price | $373 |
Good round-trip deal | $548 or less |
Good one-way deal | $246 or less |
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 2,558,603 searches. Data last updated August 5, 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
Sun 9/6
5:55 pm-10:55 pm
1 stop5h 00m
Chicago Midway
Tue 9/8
2:00 pm-5:35 pm
1 stop3h 35m
$293
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 9/19
9:40 am-2:20 pm
1 stop4h 40m
Chicago Midway
Sat 9/26
6:45 am-11:50 am
1 stop5h 05m
$294
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 8/29
9:40 am-2:20 pm
1 stop4h 40m
Chicago Midway
Mon 8/31
5:30 am-1:30 pm
1 stop8h 00m
$294
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 10/1
5:51 pm-10:44 pm
1 stop4h 53m
Chicago Midway
Sat 10/3
4:30 pm-9:41 pm
1 stop5h 11m
$299
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sun 9/20
6:00 am-9:49 am
1 stop3h 49m
Chicago Midway
Tue 9/22
1:00 pm-5:11 pm
1 stop4h 11m
$299
Quickest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 9/29
4:20 pm-8:10 pm
1 stop3h 50m
Chicago Midway
Tue 10/6
8:05 am-12:00 pm
1 stop3h 55m
$299
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 9/3
1:10 pm-7:20 pm
1 stop6h 10m
Chicago Midway
Thu 9/10
5:30 am-12:30 pm
1 stop7h 00m
$299
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 9/3
1:10 pm-10:00 pm
1 stop8h 50m
Chicago Midway
Tue 9/8
2:00 pm-5:35 pm
1 stop3h 35m
$300
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 9/10
2:40 pm-11:25 pm
2 stops8h 45m
Chicago Midway
Tue 9/15
2:00 pm-5:35 pm
1 stop3h 35m
$300
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 9/1
3:00 pm-11:10 pm
2 stops8h 10m
Chicago Midway
Tue 9/8
2:00 pm-5:35 pm
1 stop3h 35m
$300
Showing 1-10 of 21 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on 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.
Cheapflights Insights
Everything you need to know about your flight from Pensacola to Chicago Midway Airport
What is the cheapest time of day to fly from PNS to MDW?
Find hourly flight availability from Pensacola to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 5, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pensacola to Chicago Midway Airport as you normally would.
How much does it cost to fly round-trip from Pensacola to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Pensacola to Chicago Midway Airport flights typically cost between $368 and $429 in September.The cheapest round-trip price found within the last 5 days was $293 on Southwest (Sep 6-Sep 8).
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 August 5, 2026.
See what other customers who have flown with Southwest and Delta 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.
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
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
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Top 2 airlines flying from Pensacola to Midway
Discover the top 2 airlines 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 2,558,603 searches. Data last updated August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$228 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$237 | Average$397 | FlexibilityNo cancel fee | On-time63% |