Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Pensacola (VPS) to Chicago (CHI) Starting at $49

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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 $49 One Way, $98 Round Trip from Pensacola to Chicago

Prices starting at $98 for return flights and $49 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 Langham, Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Chicago Athletic Association, part of Hyatt
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More About Flying To Chicago from Pensacola

Route Information for Flights from Pensacola to Chicago

Origin Airport IATA Code VPS
Destination Airport IATA Code CHI
Distance 795 mi
Direct Flight Airlines American Airlines, Lufthansa, United Airlines
Earliest Flight Arrival 6:26PM UTC
Latest Flight Arrival 9:50PM UTC

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.

Flights from Pensacola to Chicago - Frequently Asked Questions

Am I able to catch a flight from Pensacola to Chicago now?

Our Covid-19 Travel Advisor can help you with questions about current quarantine requirements and travel restrictions when taking a flight from Pensacola to Chicago.

Are there non-stop flights from Pensacola to Chicago?

You'll find 3 airlines that offer direct services from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD), so get ready to click that "book" button. One of these popular carriers will have the flight you're looking for:

  • American Airlines
  • United Airlines
  • Frontier Airlines
What is the shortest flight from Pensacola to Chicago?

With the flight from Pensacola to Chicago taking a minimum of 3 hours and 3 minutes, you'll have plenty of time to kick back and enjoy the experience. Treat yourself to a glass of red and settle into your seat with a riveting novel or movie.

What airlines fly from Pensacola to Chicago most frequently?

American Airlines (AA) offers 39 flights every month between Pensacola, FL Airport (PNS-Pensacola Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). Your next grand adventure is only a few clicks away. If you can't find the right flight there, look into the airfares with United Airlines (UA). This airline is a fantastic alternative and offers 30 flights from Pensacola to Chicago every month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

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 Chicago 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 Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago 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 2020 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 the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. 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.