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Not ready to book? to track prices.Frontier flights from Pensacola to Chicago Midway Airport
Our best Frontier deals on Pensacola to Chicago Midway Airport flight tickets
Southwest flights from Pensacola to Chicago Midway Airport
Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
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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
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 12/10
4:10 pm-10:40 pm
1 stop6h 30m
Chicago Midway
Mon 12/14
12:45 pm-6:05 pm
1 stop5h 20m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 11/11
4:10 pm-10:45 pm
1 stop6h 35m
Chicago Midway
Tue 11/17
12:45 pm-6:10 pm
1 stop5h 25m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 11/11
7:55 am-12:55 pm
1 stop5h 00m
Chicago Midway
Tue 11/17
8:50 am-6:10 pm
2 stops9h 20m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 11/3
7:55 am-12:55 pm
1 stop5h 00m
Chicago Midway
Tue 11/10
8:50 am-3:35 pm
1 stop6h 45m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 11/2
5:55 pm-12:05 am
1 stop6h 10m
Chicago Midway
Mon 11/9
4:00 pm-8:35 pm
1 stop4h 35m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 11/21
5:25 pm-12:50 am
1 stop7h 25m
Chicago Midway
Thu 11/26
8:40 am-3:00 pm
1 stop6h 20m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 10/28
6:20 am-11:25 am
1 stop5h 05m
Chicago Midway
Mon 11/2
4:00 pm-8:30 pm
1 stop4h 30m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 12/10
4:10 pm-10:40 pm
1 stop6h 30m
Chicago Midway
Sun 12/13
8:00 am-1:40 pm
1 stop5h 40m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 11/21
6:35 pm-7:47 pm
1 stop25h 12m
Chicago Midway
Fri 11/27
8:42 pm-5:40 pm
1 stop20h 58m
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 11/12
6:00 am-10:24 am
1 stop4h 24m
Chicago Midway
Sun 11/15
6:00 am-11:09 am
1 stop5h 09m
See travel insights to Chicago from
How to get the cheapest flight ticket from Pensacola to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Pensacola, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Pensacola during the month February is also very affordable. Most momondo users find prices during this month for around $0.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Saturday departure recently was $400. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Pensacola because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $567.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Pensacola at noon is the least expensive time of day to depart. momondo users have found prices as low as $400 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $466. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Pensacola to Chicago Midway flight route?
Fly from Pensacola to Chicago Midway for the best Pensacola - Chicago Midway flight prices
What cabin class options are available on Pensacola to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Pensacola to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Pensacola to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Pensacola to Chicago Midway Airport.
When to book flights from Pensacola to Chicago Midway Airport
Cheap Pensacola to Chicago Midway Airport (PNS to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago Midway Airport
Frequently asked questions about flying from Pensacola to Chicago Midway Airport
How far is Pensacola to Chicago Midway by plane?
The distance between Pensacola and Chicago Midway is about 785.3 mi. Flights usually cover this in 2h 20m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Pensacola Airport to Chicago Midway Airport?
Prices for flights from Pensacola Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Pensacola Airport to Chicago Midway Airport?
There is 1 operator available for flights from Pensacola Airport to Chicago Midway Airport as of October 2026.
How old do you have to be to fly from Pensacola Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pensacola Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Pensacola to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Pensacola to Chicago Midway Airport is Boeing 737, representing 22.58% of all bookings. The subsequent popular models are Embraer 175 at 19.35%, Boeing 737-800 at 12.90%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 6.45%.
What is the most popular airline from Pensacola to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Pensacola to Chicago Midway Airport is Southwest (100% of total bookings).
Best airlines flying from Pensacola to Chicago Midway Airport
Compare and see reviews for airlines that fly from Pensacola to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $246 | Free Cancellation | Rating 7.9 4,228 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Pensacola to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.
Can I find flights from Pensacola to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Pensacola with this policy.
How can momondo help me find flights from Pensacola to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Pensacola. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Pensacola to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Pensacola to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.