Cheap flights from Chicago Midway Airport to Pensacola from $104
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Pensacola departing on 11/4. 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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Frontier flights from Chicago Midway Airport to Pensacola
Our best Frontier deals on Chicago Midway Airport to Pensacola flight tickets
Southwest flights from Chicago Midway Airport to Pensacola
Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to Pensacola
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 Pensacola?
The cheapest month to fly to Pensacola from Chicago Midway Airport is in January. Flight prices, which tend to average around $228, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago Midway Airport during July instead. Flights to Pensacola in July, while not as cheap as those in January, still average around $277.
What is the cheapest day to depart on your flight to Pensacola?
On average, the least expensive day to fly to Pensacola from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $326. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $462.
What is the cheapest time of day to depart on your flight to Pensacola?
The cheapest time of day to fly to Pensacola is in the afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $404. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago Midway to Pensacola flight route?
Fly from Chicago Midway to Pensacola for the best Chicago Midway - Pensacola flight prices
What cabin class options are available on Chicago Midway to Pensacola flights?
There are 1 cabin classes available to choose from on Chicago Midway to Pensacola 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 Chicago Midway Airport to Pensacola flights?
No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Pensacola.
What is the cheapest airline that flies from Chicago Midway to Pensacola?
Southwest, Delta, and Frontier are the most popular carriers operating from Chicago Midway to Pensacola
What airlines fly to Pensacola?
Southwest, Delta and Allegiant Air are the top three most popular airlines that fly to Pensacola from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Pensacola. Keep in mind that there are 3 different airlines that fly to Pensacola on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Pensacola on average per week?
As of July 2025, there are 6 flights per week flying from Chicago Midway Airport to Pensacola. The most common day of the week flights depart is Mon, with 33% of flights taking off on this day.
When to book flights from Chicago Midway Airport to Pensacola
Cheap Chicago Midway Airport to Pensacola (MDW to PNS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Pensacola
Best Price Found | $104 |
|---|---|
Fastest flight time | 2h 05m |
Direct flights | Mon, Wed, Thu, Fri and Sun |
Airports in Pensacola | 1 airport |
How far is Chicago Midway to Pensacola by plane?
Chicago Midway and Pensacola are 785.3 mi apart from one another. A reasonable flight in good conditions will take 2h 05m.
When did momondo last update prices for flights from Chicago Midway Airport to Pensacola Airport?
Prices for flights from Chicago Midway Airport to Pensacola Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Pensacola Airport?
As of July 2025, there are 2 operators available to choose from for flights from Chicago Midway Airport to Pensacola Airport.
How old do you have to be to fly from Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola Airport.
What documentation or ID do you need to fly to Pensacola Airport?
The necessary travel and health documents for your Pensacola Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Pensacola?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Pensacola is Boeing 737-800 Passenger/BBJ2 (winglets), representing 23.64% of all bookings. The subsequent popular models are Airbus A320-100/200 at 21.82%, Airbus A319 at 20.91%, and Boeing 737-700 Passenger/BBJ1 (winglets) at 19.09%.
What is the most popular airline from Chicago Midway Airport to Pensacola?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Pensacola is Southwest, representing 65% of all bookings. The subsequent popular airline is Delta at 35%.
Best airlines flying from Chicago Midway Airport to Pensacola
Compare and see reviews for airlines that fly from Chicago Midway Airport to Pensacola with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,982 reviews | |||
| PriceFrom $248 | Free Cancellation | Rating 8.0 4,266 reviews |
Southwest Flights From Chicago Midway Airport to Pensacola
Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pensacola, operating 6 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pensacola starts from $248 round-trip, up to an average price of $381. Our users have rated Southwest at 8.0/10.
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Why should I use momondo to find a flight deal from Chicago to Pensacola?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pensacola for you.
Can I find flights from Chicago to Pensacola with flexible booking policies on momondo?
All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Pensacola?
Once all potential Chicago to Pensacola flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Pensacola right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.