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Chicago to Key West 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 Key West

Departure Arrival Travel dates Round-trip
CHI EYW Tue, Jan 6 - Thu, Jan 15 $430
CHI EYW Sun, Oct 26 - Fri, Oct 31 $444
CHI EYW Tue, Oct 14 - Wed, Oct 22 $452
CHI EYW Sat, Jan 17 - Sat, Jan 24 $489

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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Cheap flights from Chicago to Key West

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4
5 6 7 8 9 10 11
12 13 14
$430
15 16 17 18
19 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 $254

Hyatt Windward Pointe

4 stars
4.5 / 5 31 reviews

3675 South Roosevelt Blvd Map

The Hyatt Windward Pointe is a luxurious vacation resort located directly across from the Atlantic Ocean and next to the Key West Airport.... More

Hotel only $169

Sunrise Suites Resort

3 stars
3.6 / 5 75 reviews

3685 Seaside Drive Map

Late Summer Savings - Save 40%

...Transportation Key West International Airport (1.1 mi./1.8 km).... Secluded Key West vacation rentals near beach offer kitchens, Wi-Fi Sunrise Suites Resort Key West offers all the convenience... More

Hotel only $160

Doubletree' Grand Key Resort

3 stars
4.0 / 5 125 reviews

3990 S. Roosevelt Blvd Map

Signature chocolate chip cookie at check-in

...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 $179

Sheraton Suites Key West

4 stars
4.2 / 5 115 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 $156

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 61 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

October

Cheapest weekend flights in October from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 Chicago (ORD) Key West (EYW) United Airlines $757
Earn $7.57
Return Sun, Nov 2 Key West (EYW) Chicago (ORD) United Airlines

Lowest roundtrip airfare in October from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 14 Chicago (MDW) Key West (EYW) Delta Air Lines $430
Earn $4.30
Return Tue, Oct 21 Key West (EYW) Chicago (MDW) Delta Air Lines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 14 Chicago (MDW) Key West (EYW) Delta Air Lines $430
Earn $4.30
Return Tue, Oct 21 Key West (EYW) Chicago (MDW) Delta Air Lines
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November

Cheapest weekend flights in November from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Nov 14 Chicago (ORD) Key West (EYW) United Airlines $682
Earn $6.82
Return Mon, Nov 17 Key West (EYW) Chicago (ORD) United Airlines

Lowest roundtrip airfare in November from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Chicago (ORD) Key West (EYW) Delta Air Lines $496
Earn $4.96
Return Wed, Dec 3 Key West (EYW) Chicago (ORD) Delta Air Lines
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December

Cheapest weekend flights in December from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 26 Chicago (ORD) Key West (EYW) American Airlines $863
Earn $8.63
Return Mon, Dec 29 Key West (EYW) Chicago (ORD) American Airlines

Lowest roundtrip airfare in December from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Dec 22 Chicago (ORD) Key West (EYW) Delta Air Lines $582
Earn $5.82
Return Fri, Dec 26 Key West (EYW) Chicago (ORD) Delta Air Lines
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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.