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Chicago to Pensacola Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Chicago to Pensacola

Departure Arrival Travel dates Round-trip
CHI PNS Sat, Nov 15 - Sun, Nov 23 $289
CHI PNS Sat, Nov 15 - Sun, Nov 23 $294
CHI PNS Sat, Nov 15 - Sun, Nov 23 $305
CHI PNS Sat, Nov 15 - Sat, Nov 22 $359

Chicago and Pensacola airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

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Airports in Pensacola FL, US
map of airports in Pensacola
  • 1

    Regional (PNS)

    Distance from City Center: 3.9 miles

  • 2

    Mobile Municipal Arpt (MOB)

    Distance from City Center: 63.8 miles

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Cheap flights from Chicago to Pensacola

Sun Mon Tue Wed Thu Fri Sat
1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
$289
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Pensacola Airport Hotels

Hotel only $101

Hampton Inn Pensacola-Airport Cordova Mall

3 stars
4.2 / 5 46 reviews

2187 Airport Boulevard Map

Free On The HouseT hot breakfast, Wi-Fi

...We are located in the heart of Pensacola's Cordova Business District, about 500 yards from Pensacola Regional Airport, with free shuttle service to the airport, Cordova Mall and area... More

Hotel only $92

Homewood Suites by Hilton Pensacola-Arpt (Cordova Mall Area)

3 stars
4.5 / 5 10 reviews

5049 Corporate Woods Drive Map

Includes parking for up to 7 nights

...in Pensacola on an extended stay, for military training or a business trip, you'll enjoy our friendly service, outdoor pool, and sports court.Our 107-suite Pensacola, FL hotel is located less... More

Hotel only $107

Hilton Garden Inn Pensacola Airport Medical Ctr.

3 stars
4.2 / 5 13 reviews

1144 Airport Boulevard Map

Complimentary wired and Wi-Fi Internet Access

...The Hilton Garden Inn Pensacola Airport/Medical Center is located just off Interstate 110 in beautiful Pensacola, Florida.... The hotel is only one mile from Pensacola Regional Airport (PNS)and... More

Hotel only $109

TownePlace Suites by Marriott Pensacola

3 stars
3.8 / 5 16 reviews

481 Creighton Road Map

...Transportation Pensacola Regional Airport (3 mi/5 km).... More

Hotel only $64

Extended Stay America - Pensacola - University Mall

2 stars
2.6 / 5 20 reviews

809 Bloodworth Lane Map

At Extended Stay America, only 8 miles from Pensacola, guests find a friendly home away from home whether they stay a day, a week or a month. Fully equipped kitchens in each of our 101 spacious... More

Hotel only $99

Courtyard by Marriott Pensacola

3 stars
4.1 / 5 23 reviews

451 Creighton Road Map

Rate includes breakfast

...Transportation Pensacola Regional Airport (4 mi/7 km) Attractions University of West Florida (0.7 mi/1 km).... More

November

Cheapest weekend flights in November from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 13 Chicago (MDW) Pensacola (PNS) Delta Air Lines $312
Earn $3.12
Return Sun, Nov 16 Pensacola (PNS) Chicago (MDW) Delta Air Lines

Lowest roundtrip airfare in November from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 15 Chicago (ORD) Pensacola (PNS) American Airlines $289
Earn $2.89
Return Sun, Nov 23 Pensacola (PNS) Chicago (ORD) American Airlines

Best one-week trip in November from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 8 Chicago (ORD) Pensacola (PNS) American Airlines $303
Earn $3.03
Return Sat, Nov 15 Pensacola (PNS) Chicago (ORD) American Airlines
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December

Cheapest weekend flights in December from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 18 Chicago (ORD) Pensacola (PNS) United Airlines $338
Earn $3.38
Return Sun, Dec 21 Pensacola (PNS) Chicago (ORD) United Airlines

Lowest roundtrip airfare in December from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 11 Chicago (ORD) Pensacola (PNS) Delta Air Lines $294
Earn $2.94
Return Thu, Dec 18 Pensacola (PNS) Chicago (ORD) Delta Air Lines

Best one-week trip in December from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Dec 11 Chicago (ORD) Pensacola (PNS) Delta Air Lines $294
Earn $2.94
Return Thu, Dec 18 Pensacola (PNS) Chicago (ORD) Delta Air Lines
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January

Lowest roundtrip airfare in January from Chicago to Pensacola

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jan 7 Chicago (MDW) Pensacola (PNS) Delta Air Lines $298
Earn $2.98
Return Sat, Jan 10 Pensacola (PNS) Chicago (MDW) Delta Air Lines
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Flights to Pensacola

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Pensacola Airport Information

Find cheap flights to Pensacola International Airport using Orbitz.com. The airport is located at 2430 Pensacola Boulevard, less than five miles from the downtown Pensacola area, and it receives flights from most major domestic and international airlines.

Ground Transportation in Pensacola

Public transportation in the Pensacola area is limited, so most visitors take a share-a-ride shuttle or taxi to get to their final destination. The city sets the taxi rates, so you can expect to pay roughly the same no matter which cab company you choose. Minimum fares are $11.00, or $2 for the first 1/9th of a mile and 25 cents for each additional 1/9th mile. Using Orbitz.com, you can book a hotel that offers free shuttle services to and from the airport or simply rent a car for the duration of your stay.

Pensacola Weather Information

Pensacola is situated in Florida's panhandle on the Gulf of Mexico coast. Winter temperatures range from the 40s to the 60s, and summers are usually somewhere between 70 and 90 degrees. Pack lightweight summer outfits during the warmer months and clothes that you can layer to accommodate milder weather during the spring, fall and winter.

What to Do in Pensacola

Sporting 52 miles of white-sandy beaches, expect many of Pensacola's activities to take place on or near the water. Urban adventurers can venture into the downtown area to take advantage of the city's many museums, historical landmarks, shopping venues and restaurants. For the best nightlife in town, head over to the Seville Quarter on East Government Street where you can enjoy live music, dining and dancing. Enjoy your trip to Pensacola, and don't forget to use Orbitz.com whenever you need to book an air ticket on one of the many cheap flights to Pensacola.