Flights from Chicago to Key West

Selected fares from Chicago to Key West

Departure Arrival Travel dates Round-trip
CHI EYW Sat, Aug 22 - Fri, Aug 28 $377
CHI EYW Fri, Oct 2 - Wed, Oct 7 $422
CHI EYW Sat, Nov 7 - Wed, Nov 11 $422
CHI EYW Mon, Aug 17 - Fri, Aug 28 $424
CHI EYW Mon, Aug 24 - Tue, Sep 1 $428
Sun Mon Tue Wed Thu Fri Sat
1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22
$393
23 24 25 26
27 28 29 30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Save more with Key West Flight + Hotel packages

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 International Airport (ORD)

    Distance from City Center: 15.1 miles

Back to menu Return to top

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 International Airport (MIA)

    Distance from City Center: 128.3 miles

Back to menu Return to top

  

Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

Featured Key West Airport Hotels

From $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

From $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

From $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

From $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

From $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

September

Lowest roundtrip airfare in September from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 22 Chicago (ORD) Key West (EYW) United Airlines $393
Earn $3.93
Return Tue, Sep 29 Key West (EYW) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Sep 22 Chicago (ORD) Key West (EYW) United Airlines $393
Earn $3.93
Return Tue, Sep 29 Key West (EYW) Chicago (ORD) United Airlines
Back to menu Return to top

October

Cheapest weekend flights in October from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 8 Chicago (ORD) Key West (EYW) US Airways $496
Earn $4.96
Return Sun, Oct 11 Key West (EYW) Chicago (ORD) US Airways

Lowest roundtrip airfare in October from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Oct 18 Chicago (ORD) Key West (EYW) United Airlines $408
Earn $4.08
Return Mon, Oct 26 Key West (EYW) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Oct 14 Chicago (ORD) Key West (EYW) Delta Air Lines $472
Earn $4.72
Return Wed, Oct 21 Key West (EYW) Chicago (ORD) Delta Air Lines
Back to menu Return to top

November

Cheapest weekend flights in November from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Nov 13 Chicago (ORD) Key West (EYW) jetBlue $655
Earn $6.55
Return Mon, Nov 16 Key West (EYW) Chicago (ORD) jetBlue

Lowest roundtrip airfare in November from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 7 Chicago (ORD) Key West (EYW) United Airlines $393
Earn $3.93
Return Wed, Nov 11 Key West (EYW) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 21 Chicago (ORD) Key West (EYW) American Airlines $859
Earn $8.59
Return Sat, Nov 28 Key West (EYW) Chicago (ORD) American Airlines
Back to menu Return to top

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 Mon, Aug 3, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA2458/AA4328 ORD 5:00 AM EYW 10:35 AM 738/E75 4hr 35min
American Airlines/US Airways AA2458/US4328 ORD 5:00 AM EYW 10:35 AM 738/E75 4hr 35min
US Airways/American Airlines US2458/AA4328 ORD 5:00 AM EYW 10:35 AM 738/E75 4hr 35min
US Airways/US Airways US2458/US4328 ORD 5:00 AM EYW 10:35 AM 738/E75 4hr 35min
Delta Air Lines/Delta Air Lines DL2030/DL1355 MDW 6:00 AM EYW 11:34 AM 717/73W 4hr 34min
Delta Air Lines/Delta Air Lines DL977/DL1355 ORD 6:00 AM EYW 11:34 AM 717/73W 4hr 34min
American Airlines/American Airlines AA2458/AA3352 ORD 5:00 AM EYW 11:44 AM 738/ER4 5hr 44min
American Airlines/US Airways AA2458/US3352 ORD 5:00 AM EYW 11:44 AM 738/ER4 5hr 44min
American Airlines/American Airlines AA1411/AA3352 ORD 6:00 AM EYW 11:44 AM 738/ER4 4hr 44min
American Airlines/US Airways AA1411/US3352 ORD 6:00 AM EYW 11:44 AM 738/ER4 4hr 44min
US Airways/American Airlines US2458/AA3352 ORD 5:00 AM EYW 11:44 AM 738/ER4 5hr 44min
US Airways/US Airways US2458/US3352 ORD 5:00 AM EYW 11:44 AM 738/ER4 5hr 44min
US Airways/American Airlines US1411/AA3352 ORD 6:00 AM EYW 11:44 AM 738/ER4 4hr 44min