Cheap flights from Pensacola to Chicago from $79
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago departing on 8/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Delta flights from Pensacola to Chicago Midway Airport
Our best Delta 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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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 day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Thursday departure recently was $327. 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, Sunday 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 $576.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Pensacola in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $329 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $380. 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 flights?
There are 1 cabin classes available to choose from on Pensacola to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Pensacola to Chicago Midway Airport on average per week?
As of June 2025, 5 flights take off from Pensacola and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.
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
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 15m, 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 are 2 operators available for flights from Pensacola Airport to Chicago Midway Airport as of June 2025.
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 737-800 Passenger/BBJ2 (winglets), representing 26.67% of all bookings. The subsequent popular models are Airbus A319 at 23.33%, Airbus A320-100/200 at 20.00%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 10.00%.
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 (58% of total bookings). The next most popular airline is Delta (42%).
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 $216 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $228 | Free Cancellation | Rating 8.0 7,950 reviews |
Southwest Flights From Pensacola to Chicago Midway Airport
Southwest is one of the most popular airlines flying from Pensacola to Chicago Midway Airport, operating 5 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago Midway Airport starts from $216 round-trip, up to an average price of $330. Our users have rated Southwest at 8.0/10.
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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.