$159+ Cheap flights from Pensacola (PNS) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Dec 6 — Dec 131
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 November 6, 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 November 6, 2026.
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:14 pm -
1 stop23h 33m
Tue 11/248:42 pm -
1 stop20h 53m
Deal found 11/2![Frontier logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 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 11/5![Frontier logo]()
$288
This Orbitz deal was found by Cheapflights users on 11/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:30 pm -
1 stop25h 17m
Fri 11/278:42 pm -
1 stop20h 58m
Deal found 11/1![Frontier logo]()
$293
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2610:01 pm -
1 stop21h 29m
Tue 12/298:35 pm -
1 stop20h 47m
Deal found 11/1![Frontier logo]()
$313
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:01 pm -
1 stop21h 29m
Sun 1/38:35 pm -
1 stop20h 47m
Deal found 11/5![Frontier logo]()
$315
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 12/311:59 am -
1 stop4h 17m
Mon 12/76:00 am -
1 stop6h 44m
Deal found 11/4![Delta logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:40 pm -
1 stop26h 07m
Tue 11/248:42 pm -
1 stop20h 53m
Deal found 11/4![Frontier logo]()
$318
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:40 pm -
1 stop26h 07m
Sun 11/228:42 pm -
1 stop20h 53m
Deal found 11/2![Frontier logo]()
$319
This Southwest deal was found by Cheapflights users on 11/2. 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 12/196:25 pm -
1 stop6h 00m
Mon 1/412:45 pm -
2 stops7h 50m
Deal found 11/2![Southwest logo]()
$322
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 November 6, 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 November 6, 2026.
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop6h 04m
Mon 12/71:02 pm -
1 stop7h 00m
Deal found 11/3![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 11/1. 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.
Fri 1/152:20 pm -
2 stops8h 40m
Tue 1/197:00 am -
1 stop8h 00m
Deal found 11/1![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 1/145:58 pm -
1 stop4h 19m
Tue 1/1910:51 am -
1 stop5h 49m
Deal found 11/4![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 11/1. 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.
Wed 12/27:55 am -
2 stops7h 35m
Sun 12/66:30 am -
2 stops7h 10m
Deal found 11/1![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 11/1. 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.
Thu 11/196:00 am -
1 stop4h 24m
Thu 11/264:13 pm -
1 stop5h 51m
Deal found 11/1![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 12/27:55 am -
2 stops7h 35m
Wed 12/910:55 am -
2 stops9h 15m
Deal found 11/4![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 11/3. 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 12/107:55 am -
2 stops6h 35m
Sun 12/136:30 am -
2 stops7h 10m
Deal found 11/3![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 11/137:01 am -
1 stop4h 58m
Mon 11/165:13 pm -
1 stop6h 28m
Deal found 11/2![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 11/1. 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.
Thu 12/177:45 am -
2 stops10h 10m
Sun 12/2010:05 am -
2 stops9h 05m
Deal found 11/1![Southwest logo]()
$408
This Southwest deal was found by Cheapflights users on 11/5. 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.
Wed 12/236:20 pm -
1 stop6h 00m
Sun 12/277:20 pm -
1 stop4h 05m
Deal found 11/5![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 12/37:55 am -
2 stops6h 35m
Thu 12/108:50 am -
2 stops9h 20m
Deal found 11/2![Southwest logo]()
$437
Last-minute flights from Pensacola to MidwayDiscover last-minute flight deals from Pensacola to Midway. Data last updated November 6, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Midway. Data last updated November 6, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:14 pm -
1 stop23h 33m
Tue 11/248:42 pm -
1 stop20h 53m
Deal found 11/2![Frontier logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 11/5. 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 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 11/5![Frontier logo]()
$288
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:40 pm -
1 stop26h 07m
Tue 11/248:42 pm -
1 stop20h 53m
Deal found 11/4![Frontier logo]()
$318
This Trip.com deal was found by Cheapflights users on 11/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:40 pm -
1 stop26h 07m
Sun 11/228:42 pm -
1 stop20h 53m
Deal found 11/2![Frontier logo]()
$319
This Orbitz deal was found by Cheapflights users on 11/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:30 pm -
1 stop25h 17m
Fri 11/278:42 pm -
1 stop20h 58m
Deal found 11/1![Frontier logo]()
$293
This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 12/311:59 am -
1 stop4h 17m
Mon 12/76:00 am -
1 stop6h 44m
Deal found 11/4![Delta logo]()
$317
This Trip.com deal was found by Cheapflights users on 11/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:01 pm -
1 stop21h 29m
Sun 1/38:35 pm -
1 stop20h 47m
Deal found 11/5![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 11/2. 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 12/196:25 pm -
1 stop6h 00m
Mon 1/412:45 pm -
2 stops7h 50m
Deal found 11/2![Southwest logo]()
$322
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2610:01 pm -
1 stop21h 29m
Tue 12/298:35 pm -
1 stop20h 47m
Deal found 11/1![Frontier logo]()
$313
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 November 6, 2026.
Search for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated November 6, 2026.
This Delta deal was found by Cheapflights users on 11/5. 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.
Tue 12/16:00 am -
1 stop4h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:05 pm -
2 stops16h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/167:46 pm -
2 stops28h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$185
This Delta deal was found by Cheapflights users on 11/1. 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.
Sat 11/146:00 am -
1 stop4h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Delta logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Wed 12/306:17 pm -
2 stops17h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$203
This Delta deal was found by Cheapflights users on 11/4. 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 11/215:24 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Sun 11/2212:45 pm -
3 stops23h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 11/1912:45 pm -
3 stops23h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/312:45 pm -
3 stops25h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 11/3. 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 11/197:55 am -
2 stops6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 11/307:46 pm -
2 stops15h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$234
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 November 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (CheapOair) |
One-way from | $159 (Delta) |
Popular in | August |
Cheapest in | June |
Average price | $542 |
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 November 6, 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 12/1
7:05 pm-11:33 am
2 stops16h 28m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$173
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Fri 11/20
6:00 am-11:59 am
1 stop5h 59m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
Quickest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 11/14
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 12/30
6:17 pm-12:10 pm
2 stops17h 53m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 11/19
12:45 pm-11:55 am
3 stops23h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$223
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Fri 11/20
2:15 pm-11:10 pm
2 stops8h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 11/19
7:55 am-2:30 pm
2 stops6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sun 11/15
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/9
2:15 pm-11:15 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sun 11/22
5:25 am-12:00 pm
2 stops6h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
Showing 1-10 of 23 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 November 6, 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.
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
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
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 November 6, 2026.
Pensacola and Midway flights
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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 November 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$400 | FlexibilityNo cancel fee | On-time63% |