Cheap Flights from Chicago (CHIA) to Pensacola (PNS)

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Flight deals from Chicago to Pensacola

Looking for a cheap last-minute deal or the best return flight from Chicago to Pensacola? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Pensacola

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Pensacola flights are currently cheapest in July.

Direct flights from Chicago to Pensacola

Chicago to Pensacola: Alternative routes

Compare routes from Chicago to Pensacola below. You may find an airport to fly into that's cheaper, faster, or easier than Pensacola.

Chicago to Pensacola: Flight information

The things to know before you go.
Cheapest flight found$264
Cheapest month to flyJuly
Average flight time2 hrs, 16 mins
Most popular airlineUnited
Average flights per week40

Finding cheap flights from Chicago to Pensacola: Frequently asked questions

The best price we found for a return flight from Chicago to Pensacola is $264. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 15 minutes is the average flight time from Chicago to Pensacola.
United, Air New Zealand and Southwest Airlines fly direct from Chicago to Pensacola.
As of June 2025, there are 20 flights per week flying from Chicago to Pensacola.
The cheapest month to fly from Chicago to Pensacola is usually July.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Pensacola Airport on Wednesday, 23 July 2025.
Yes – the average flight time is 2 hours and 15 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Pensacola but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Pensacola is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Chicago to Pensacola International Airport (PNS): What you need to know

  • Start planning your holiday by looking up the most convenient departure point for your flight from Chicago to Pensacola International Airport (PNS). Explore the options for setting off from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), the city's main airports.

  • Take off on a direct Chicago to Pensacola International Airport flight and you'll be in the air for around 2 hours 20 minutes.

  • Pensacola International Airport is located in Pensacola. The city's timezone is UTC-5 — the same as Chicago.

  • O'Hare International Airport (ORD) to Pensacola International Airport (PNS) is the busiest route, with 8 direct services every week. Get from ORD to PNS on United Airlines's 7:10am flight.

  • Get to the airport on time so you don't miss your flight from Chicago to PNS. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the mad dash to your gate.

  • If you're jetting off during a bank holiday or other peak period, allow extra time. Get there two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can take a direct flight from Chicago to Pensacola International Airport (PNS) departing from O'Hare International Airport (ORD).

  • At ORD, you'll find a variety of airlines operating direct flights from Chicago to Pensacola International Airport, including:

  • The most frequently booked airline between ORD and PNS is United Airlines.

  • With a dependable 82.54% of services arriving on schedule, United Airlines is the most punctual carrier operating on this route.

  • The journey from central Chicago to ORD takes about 55 minutes by public transport. If you drive, ride-share or grab a cab, you'll cover the 40 kilometres in 35 minutes or so, depending on traffic.

  • In search of a comfortable hotel near O'Hare International Airport? If you're catching an early flight from Chicago to Pensacola International Airport, these stays will have you sleeping moments from your check-in counter:

  • 74.85% of flights that leave from O'Hare International Airport touch down at their destination on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can book a direct Chicago to Pensacola International Airport (PNS) flight ticket out of Chicago Midway International Airport (MDW). Figure out if flying from MDW works better for your plans.

  • Catch your direct flight from Chicago to PNS with Southwest Airlines. This is one of the top airlines that operates this route out of MDW.

  • Southwest Airlines is the most popular choice for passengers flying from MDW to PNS.

  • With public transport, you can travel from central Chicago to MDW in about 45 minutes. The terminal is roughly 19 kilometres away, and making the journey by car takes approximately 20 minutes.

  • Want to enjoy an extra night away before boarding your Chicago to PNS flight? Unwind in a hotel near Chicago Midway International Airport before your adventure officially begins. These stays have a room with your name on it:

  • 77.88% of flights taking off from Chicago Midway International Airport make it to their destination as expected.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey to RFD from central Chicago is around 4 hours 15 minutes on public transport. If you prefer to travel by car, it'll take you roughly 1 hour 25 minutes to cover the 137 kilometres or so.

  • Make catching an early Chicago to Pensacola International Airport flight the easiest part of your journey. Stay at one of these hotels near Chicago Rockford International Airport and get to your gate feeling relaxed and unhurried:

  • Flights that depart from RFD make it to their destination within the scheduled time frame 76.19% of the time.

  • The street address of Chicago Rockford International Airport is 2 Airport Cir.

About Pensacola International Airport (PNS)

Getting from Pensacola International Airport (PNS) to central Pensacola

  • Pensacola International Airport to the centre of Pensacola is around 6 kilometres. If you're renting a car or taking a cab, plan ahead to make your trip as smooth as possible. Journey times vary depending on the time of day and traffic conditions.

  • When travelling on public transport, expect a journey time of around 1 hour 40 minutes.

How to find the cheapest flights from Chicago to Pensacola International Airport (PNS)

  • The lowest price we've found for a one-way ticket from Chicago to Pensacola International Airport is $124. For a return flight on this route, the best price is $264. Depending on how early you book and the availability, these fares could change.

  • Book one month before your departure date. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to PNS.

  • June is when you're most likely to land a bargain on a Chicago to Pensacola International Airport ticket. If you're looking to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • There's no need to search every day to find out if prices have dropped when you create a Price Alert. We'll let you know the moment a new deal shows up on flight tickets from Chicago to PNS.

  • Tailor your travel plans using filters. Choose your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from Chicago to Pensacola International Airport.

The best time to fly from Chicago to Pensacola International Airport (PNS)

  • July is the most popular month for flights from Chicago to Pensacola International Airport (PNS). Plan your visit to Pensacola in February for a quieter experience.

  • The warmest month in Pensacola is August, with temperatures ranging between 24ºC (75ºF) and 35ºC (95ºF). Lock in your Chicago to PNS flight ticket then if you enjoy this type of weather.

  • Look for cheap tickets from Chicago to Pensacola International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 2ºC (36ºF) and 19ºC (66ºF).

More about Pensacola

Explore more of the United States

  • Pensacola has its own special appeal, but there are so many other parts of the United States just waiting to be discovered. About 290 kilometres west of Pensacola, a trip to New Orleans will keep your itinerary busy. Start with leading sights like Bourbon Street, French Quarter and Cafe Du Monde.

  • If you're interested in discovering another well-known destination in the United States, head for Montgomery, about 225 kilometres north of Pensacola. Civil Rights Memorial, Natl memorial for peace and Dexter Avenue King Memorial Baptist Church are key reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.