Cheap Flight Deals From Chicago (CHI) to Pensacola (PNS) Starting at $92

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This Weekend's Flight Deals from Chicago to Pensacola

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $92 One Way, $168 Round Trip from Chicago to Pensacola

Prices starting at $168 for return flights and $92 for one-way flights to Pensacola were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Pensacola economy flight packages

Sandestin Golf and Beach Resort
Destin Holiday Beach Resort
Hilton Sandestin Beach Golf Resort & Spa
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More About Flying To Pensacola from Chicago

Route Information for Flights from Chicago to Pensacola

Origin Airport IATA Code CHI
Destination Airport IATA Code PNS
Distance 795 mi
Direct Flight Airlines United Airlines
Earliest Flight Arrival 7:15PM UTC
Latest Flight Arrival 7:15PM UTC

Travel from Chicago to Pensacola

When you’re ready to escape the Windy City for some fun in the sun on a subtropical beach, let yourself get tempted by the cheap flights from Chicago to Pensacola found on

Leaving Chicago

Most travelers flying out of Chicago leave from Chicago O’Hare International Airport, located about seventeen miles northwest of the city. Another option is to fly out of the smaller Chicago Midway International Airport, which is about ten miles south of the city. O’Hare offers the only available nonstop flight to Pensacola from Chicago. Both airports are accessible by taxi, public bus, and rail. The Chicago Transit Authority Blue line serves O’Hare and the Orange line serves Midway. For those who drive to the airport, economy parking is available for $9 per day at O’Hare and $14 per day at Midway.

Exploring the Florida Panhandle

After arriving at Pensacola International Airport, you can find quick and convenient transportation into town via a local taxi or airport shuttle service. Eight car rental agencies have offices onsite at the airport if you prefer to rent a car while in Pensacola. While the sandy beaches and warm Gulf waters are a big draw for most visitors, Pensacola is also home to many other fascinating attractions, such as the National Naval Aviation Museum and Fort Pickens. Summer is high season in Pensacola, and with average highs in the 90s, most visitors and locals hit the beaches for water-based fun during the summer months. Winter highs average in the 60s, so it is typically pleasant enough for sightseeing but not quite warm enough for a swim. The weather in September and October remains warm enough to swim, with highs in the 70s and 80s, and prices are lower during this shoulder season. Late March, April, and May enjoy similar weather, but the beaches can get crowded during this time because many college students head to Pensacola for spring break.

Visiting Pensacola

Whether your vacation plans involve watersports and wildlife exploration or just laying out on one of Pensacola’s fabulous white-sand beaches, you can start planning your dream getaway by searching for cheap flights from Chicago to Pensacola on

Frequently asked questions

Am I able to catch a flight from Chicago to Pensacola now?
If you’re agonizing over travel restrictions and quarantine requirements when getting a flight from Chicago to Pensacola, go right to our Covid-19 Travel Advisor.
Are there non-stop flights from Chicago to Pensacola?
Start packing that suitcase, because there are a couple of airlines that offer nonstop flights from O’Hare Airport to Pensacola Airport. Check out the fares with United Airlines and American Airlines.
What is the shortest flight from Chicago to Pensacola?
It can zip by in as little as 2 hours and 45 minutes. If you believe your vacation hours should be spent ‘vacationing’ instead of flying, you’ll enjoy the flight from Chicago to Pensacola.
What airlines fly from Chicago to Pensacola most frequently?
Consider booking a ticket with United Airlines (UA), which flies frequently along this route. This airline operates 30 flights each month between Chicago, IL (ORD-O’Hare Intl.) and Pensacola, FL (PNS-Pensacola Intl.). If you want a few more options, check out the fares with American Airlines (AA), which has 30 flights from Chicago to Pensacola every month.
If I am not able to travel due to COVID-19, can I cancel my flight to Pensacola?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Pensacola have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Pensacola with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Pensacola without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.