
$77 Cheap flight deals from Pensacola (PNS) to Chicago (CHI)
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This Weekend's Flight Deals from Pensacola to Chicago
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 $77 One Way, $156 Round Trip from Pensacola to Chicago
Prices starting at $156 for return flights and $77 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages

The Royal Sonesta Chicago Downtown
Dec 12 - Dec 15
Pensacola (PNS) to Chicago (ORD)
Chicago (ORD) to Pensacola (PNS)
Reviewed on Oct 19, 2025

Hotel Riu Plaza Chicago
Dec 12 - Dec 15
Pensacola (PNS) to Chicago (ORD)
Chicago (ORD) to Pensacola (PNS)
Reviewed on Sep 2, 2025

Fairmont Chicago at Millennium Park
Dec 12 - Dec 15
Pensacola (PNS) to Chicago (ORD)
Chicago (ORD) to Pensacola (PNS)
Reviewed on Oct 10, 2025
More About Flying To Chicago from Pensacola
Route Information for Flights from Pensacola to Chicago
Origin Airport IATA Code | PNS |
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Destination Airport IATA Code | CHI |
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Book Your Flight from Pensacola to Chicago
Pensacola Airport Information
Use Orbitz.com to find cheap flights from Pensacola and choose from any of the major domestic airlines that service the airport, including AirTran, US Airways Express, American Eagle, United, Delta and Delta Connection. Pensacola International Airport serves Florida's greater Pensacola region from its central location just five miles north of the downtown area. Getting to the airport from the city is easy by taking 9th Avenue to 12th Avenue to Airport Boulevard.
Airport Parking in Pensacola
You have three parking options at the Pensacola airport. Surface lots are located within easy walking distance of the terminal, with a maximum rate of $8.50 per day. Overflow parking is available in the shuttle lot for the same $8.50-per-day rate, and the airport offers free shuttle service to take you back and forth to the terminal from your car. Covered garage parking is also available for $10.50 per day
Ground Transportation in Pensacola
The most economical way to get to the airport from the city is via a share-a-ride shuttle or taxi. Reserve your shuttle in advance to get to the airport on time. The city of Pensacola sets standard taxi rates, so you should be charged the same amount no matter what cab company you choose. Expect to pay $2 for the first 1/9th mile and $.25 for each additional 1/9th mile, with an $11 minimum fare. Save enough money to hire a private car service when you use Orbitz.com to purchase discount air tickets.
Restaurants in the Pensacola Airport
There is only one full bar and sit-down restaurant inside the Pensacola airport. Varona's Restaurant is located in the public area before the security checkpoint. Once you have entered the post-security gate areas, your purchases are limited to grab-and-go snacks and beverages. If you are about to embark on a long flight, you might want to consider stopping at one of the full-service restaurants just outside of the airport, such as Bonefish Grill on 12th Avenue or O'Brien's Bistro on Bayou Boulevard. Enjoy your travels, and remember to use Orbitz.com the next time you want to find cheap flights from Pensacola.
Airports in Chicago
Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.
Transportation from the Airport
Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.
Weather in Chicago
Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.
Highlights and Attractions
Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.
Frequently asked questions
- Flights to Chicago
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Flights from Pensacola
- Pensacola to Orlando
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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.