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Chicago to Key West Flights

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 Key West

Departure Arrival Travel dates Round-trip
CHI EYW Tue, Jan 13 - Thu, Jan 22 $373
CHI EYW Sun, Jan 11 - Wed, Jan 14 $376
CHI EYW Mon, Feb 9 - Wed, Feb 18 $376
CHI EYW Thu, Jan 22 - Tue, Jan 27 $376

Chicago and Key West 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 Key West FL, US
map of airports in Key West
  • 1

    Key West International (EYW)

    Distance from City Center: 2.9 miles

  • 2

    Miami Airport (MIA)

    Distance from City Center: 128.3 miles

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Sun Mon Tue Wed Thu Fri Sat
1 2 3
4 5 6 7 8 9 10
11
$373
12
$373
13
$373
14 15 16 17
18
$373
19
$373
20 21 22 23 24
25 26 27 28 29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Key West Airport Hotels

Hotel only $279

Hyatt Windward Pointe

4 stars
4.5 / 5 32 reviews

3675 South Roosevelt Blvd Map

...Transportation Key West International Airport (0.2 mi/0.3 km).... On the southeast side of Key West, the Hyatt Windward Pointe offers a secluded getaway with residential-style accommodations... More

Hotel only $179

Sunrise Suites Resort

3 stars
3.6 / 5 78 reviews

3685 Seaside Drive Map

Winter Sale - Save 30%

Sunrise Suites Resort Key West offers all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom, 2 bath condos located just minutes from Smathers Beach and 2... More

Hotel only $170

Doubletree' Grand Key Resort

3 stars
4.0 / 5 128 reviews

3990 S. Roosevelt Blvd Map

Rate includes a $50 USD daily hotel credit

...Transportation Key West International Airport (1.1 mi./1.8 km).... Mid-range rooms and suites with free shuttle service and pet policy The Green Lodging-certified Doubletree Grand Key Resort... More

Hotel only $148

Sheraton Suites Key West

4 stars
4.2 / 5 119 reviews

2001 South Roosevelt Boulevard Map

Save 40% on your stay

...Transportation Key West International Airport (1.1 mi./1.8 km).... The airport adjacent hotel offers suites decorated in Caribbean colors, and the property has undergone a recent renovation... More

Hotel only $151

Coconut Mallory Resort and Marina by Kees Vacations

3 stars
3.8 / 5 40 reviews

1445 S. Roosevelt Blvd. Map

...Located just after the entrance to the island, the resort sits near the Key West airport and less than five miles from Mallory Square and the popular attractions along Duval Street....... More

Hotel only $159

Ibis Bay Resort

2 stars
3.4 / 5 62 reviews

3101 North Roosevelt Blvd Map

Located just outside of Old Town Key West, the Ibis Bay Resort provides a true feel of Key West with great food, fun, and excitement, while still giving you the rest and relaxation that brought you... More

January

Cheapest weekend flights in January from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jan 29 Chicago (ORD) Key West (EYW) American Airlines $381
Earn $3.81
Return Mon, Feb 2 Key West (EYW) Chicago (ORD) American Airlines

Lowest roundtrip airfare in January from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Jan 19 Chicago (ORD) Key West (EYW) US Airways $373
Earn $3.73
Return Fri, Jan 23 Key West (EYW) Chicago (ORD) US Airways

Best one-week trip in January from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Jan 3 Chicago (ORD) Key West (EYW) US Airways $492
Earn $4.92
Return Sat, Jan 10 Key West (EYW) Chicago (ORD) US Airways
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February

Cheapest weekend flights in February from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 26 Chicago (ORD) Key West (EYW) American Airlines $445
Earn $4.45
Return Sun, Mar 1 Key West (EYW) Chicago (ORD) American Airlines

Lowest roundtrip airfare in February from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Feb 9 Chicago (ORD) Key West (EYW) US Airways $373
Earn $3.73
Return Wed, Feb 18 Key West (EYW) Chicago (ORD) US Airways

Best one-week trip in February from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 5 Chicago (ORD) Key West (EYW) United Airlines $390
Earn $3.90
Return Thu, Feb 12 Key West (EYW) Chicago (ORD) United Airlines
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March

Lowest roundtrip airfare in March from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 3 Chicago (ORD) Key West (EYW) US Airways $431
Earn $4.31
Return Tue, Mar 10 Key West (EYW) Chicago (ORD) US Airways

Best one-week trip in March from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 3 Chicago (ORD) Key West (EYW) US Airways $431
Earn $4.31
Return Tue, Mar 10 Key West (EYW) Chicago (ORD) US Airways
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Flights to Key West

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.

Key West International Airport

With warm weather, amazing views, and dozens of outdoor activities, Key West is a popular vacation spot. Looking for cheap flights to Key West doesn't have to be stressful. Orbitz.com offers discounts on flights to the island from many locations. Key West International Airport is the only airport in this area. Several major airlines operate out of the airport, including Southwest Airlines, Delta Air Lines, American Eagle and US Airways Express.

Getting to Downtown

Since the airport is only two miles from downtown, you can get to almost any downtown spot within 10 to 20 minutes. Many travelers rent a car from one of the companies operating out of the airport, such as Thrifty, Enterprise or Budget. You can also take the Keys Shuttle, which is a large bus that makes stops at the airport throughout the day and drops off passengers at multiple spots around Key West.

Key West Weather

The late spring through late fall is the rainy season in Key West, and the area has more than 50 rainy days throughout this season. Temperatures during the summer can easily reach the high 80s or low 90s, while winter temperatures typically range from the mid 60s to low 70s. When you book your air ticket, make sure that you plan ahead for wet weather.

Festivals and Events

Top local events include Bike Week, Fantasy Fest, Key West Race Week, Hemingway Days Festival, and Key West Songwriters Festival. With Orbitz.com, you can get deals on your hotel room, rental car and on cheap flights to Key West. No matter when you visit, you can make your travel arrangements quickly.

Flight schedule for flights from Chicago to Key West on Sun, Dec 21, 2014

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA1342/AA2961 ORD 5:00 AM EYW 10:57 AM 738/ER4 4hr 57min
American Airlines/US Airways AA1342/US8266 ORD 5:00 AM EYW 10:57 AM 738/ER4 4hr 57min
US Airways/American Airlines US1342/AA2961 ORD 5:00 AM EYW 10:57 AM 738/ER4 4hr 57min
US Airways/US Airways US1342/US8266 ORD 5:00 AM EYW 10:57 AM 738/ER4 4hr 57min
American Airlines/Silver Airways AA1238/3M125 ORD 5:45 AM EYW 1:18 PM 738/SF3 6hr 33min
American Airlines/United Airlines AA1238/UA3125 ORD 5:45 AM EYW 1:18 PM 738/SF3 6hr 33min
American Airlines/Silver Airways AA1463/3M125 ORD 7:10 AM EYW 1:18 PM 738/SF3 5hr 8min
American Airlines/United Airlines AA1463/UA3125 ORD 7:10 AM EYW 1:18 PM 738/SF3 5hr 8min
US Airways/Silver Airways US1238/3M125 ORD 5:45 AM EYW 1:18 PM 738/SF3 6hr 33min
US Airways/United Airlines US1238/UA3125 ORD 5:45 AM EYW 1:18 PM 738/SF3 6hr 33min
US Airways/Silver Airways US1463/3M125 ORD 7:10 AM EYW 1:18 PM 738/SF3 5hr 8min
US Airways/United Airlines US1463/UA3125 ORD 7:10 AM EYW 1:18 PM 738/SF3 5hr 8min
American Airlines/Silver Airways AA2317/3M113 ORD 7:30 AM EYW 1:38 PM 738/SF3 5hr 8min