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Fares from $85 One Way, $169 Round Trip from Pensacola to Chicago

Prices starting at $169 for return flights and $85 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.

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More About Flying To Chicago from Pensacola

Flights from Pensacola to Chicago - Frequently Asked Questions

Are there non-stop flights from Pensacola to Chicago?

The awesome news is, there are. United Airlines and American Airlines are a couple of carriers that will fly you straight from Pensacola, FL Airport (PNS-Pensacola Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.).

What is the shortest flight from Pensacola to Chicago?

It can take just 2 hours and 33 minutes to fly from Pensacola, FL Airport (PNS-Pensacola Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). Sit back and enjoy the service, because you'll be touching down in the blink of an eye.

What airlines fly from Pensacola to Chicago most frequently?

Consider booking a flight with United Airlines (UA), which flies frequently along this route. This airline offers 26 flights every month between Pensacola, FL Airport (PNS-Pensacola Intl.) and Chicago, IL Airport (ORD-O'Hare Intl.). Alternatively, secure your favorite window (or aisle) seat with American Airlines (AA). You'll have 2 monthly flights between Pensacola and Chicago to take your pick of with this company.

Route Information for Flights from Pensacola to Chicago

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Destination Airport IATA CodeCHI
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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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.