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Pensacola to Chicago 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 Pensacola to Chicago

Departure Arrival Travel dates Round-trip
PNS CHI Thu, Oct 30 - Sun, Nov 2 $294
PNS CHI Wed, Dec 17 - Wed, Jan 7 $351
PNS CHI Thu, Oct 30 - Sun, Nov 2 $387
PNS CHI Thu, Oct 30 - Sun, Nov 2 $405

Pensacola and Chicago airports and terminals

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

    Regional (PNS)

    Distance from City Center: 3.9 miles

    Carriers for flights from PNS to CHI

    Carriers
    United Airlines
  • 2

    Mobile Municipal Arpt (MOB)

    Distance from City Center: 63.8 miles

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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

    Terminals and carriers for flights from PNS to ORD

    Terminal Carriers
    Terminal 1 United Airlines
    Terminal 2 United Airlines
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Cheap flights from Pensacola to Chicago

Sun Mon Tue Wed Thu Fri Sat
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$294
31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 123 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 42 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 14 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 109 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

October

Cheapest weekend flights in October from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 Pensacola (PNS) Chicago (MDW) Delta Air Lines $294
Earn $2.94
Return Sun, Nov 2 Chicago (MDW) Pensacola (PNS) Delta Air Lines

Lowest roundtrip airfare in October from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 Pensacola (PNS) Chicago (MDW) Delta Air Lines $294
Earn $2.94
Return Sun, Nov 2 Chicago (MDW) Pensacola (PNS) Delta Air Lines
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November

Cheapest weekend flights in November from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Nov 21 Pensacola (PNS) Chicago (ORD) Delta Air Lines $349
Earn $3.49
Return Sun, Nov 23 Chicago (ORD) Pensacola (PNS) Delta Air Lines

Lowest roundtrip airfare in November from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Nov 16 Pensacola (PNS) Chicago (MDW) Delta Air Lines $294
Earn $2.94
Return Sun, Jan 11 Chicago (MDW) Pensacola (PNS) Delta Air Lines

Best one-week trip in November from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Nov 25 Pensacola (PNS) Chicago (ORD) Delta Air Lines $316
Earn $3.16
Return Tue, Dec 2 Chicago (ORD) Pensacola (PNS) Delta Air Lines
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December

Lowest roundtrip airfare in December from Pensacola to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 17 Pensacola (PNS) Chicago (ORD) Delta Air Lines $316
Earn $3.16
Return Wed, Jan 7 Chicago (ORD) Pensacola (PNS) Delta Air Lines
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Flights 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.

Aircraft options between Pensacola and Chicago

Equipment Carrier
Embraer RJ135/RJ140/RJ145 United Airlines