Search for flights

Flight type Round-trip One-way
Age categories
Age of children at time of trip

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

Additional search options

Chicago to Key West Flights

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.

Cheap flights from Chicago to Key West

Prices are for round-trip flights per adult (taxes and fees included)

Cheapest fares highlighted below

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

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

June

Cheapest weekend flights in June from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 20 Chicago (ORD) Key West (EYW) American Airlines $476
Return Mon, Jun 24 Key West (EYW) Chicago (ORD) American Airlines

Lowest roundtrip airfare in June from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 20 Chicago (ORD) Key West (EYW) Delta Air Lines $476
Return Sat, Jun 29 Key West (EYW) Chicago (ORD) Delta Air Lines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Jun 30 Chicago (ORD) Key West (EYW) United Airlines $492
Return Sun, Jul 7 Key West (EYW) Chicago (ORD) United Airlines
Back to menu Return to top

July

Cheapest weekend flights in July from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 18 Chicago (ORD) Key West (EYW) United Airlines $488
Return Mon, Jul 22 Key West (EYW) Chicago (ORD) United Airlines

Lowest roundtrip airfare in July from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jul 23 Chicago (ORD) Key West (EYW) Delta Air Lines $476
Return Tue, Jul 30 Key West (EYW) Chicago (ORD) Delta Air Lines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jul 23 Chicago (ORD) Key West (EYW) Delta Air Lines $476
Return Tue, Jul 30 Key West (EYW) Chicago (ORD) Delta Air Lines
Back to menu Return to top

August

Cheapest weekend flights in August from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Aug 22 Chicago (ORD) Key West (EYW) United Airlines $476
Return Sun, Aug 25 Key West (EYW) Chicago (ORD) United Airlines

Lowest roundtrip airfare in August from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Aug 31 Chicago (ORD) Key West (EYW) United Airlines $464
Return Sat, Sep 7 Key West (EYW) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Aug 31 Chicago (ORD) Key West (EYW) United Airlines $464
Return Sat, Sep 7 Key West (EYW) Chicago (ORD) United Airlines
Back to menu Return to top
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

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 Airport (MIA)

    Distance from City Center: 128.3 miles

Back to menu Return to top

Cheap airline tickets from Chicago to Key West

Airline Departure Arrival Travel dates Round-trip
airline logo United Airlines CHI EYW Thu, Aug 29 - Thu, Sep 5 $464
Delta Airlines Delta Air Lines CHI EYW Thu, Aug 29 - Thu, Sep 5 $476
airline logo American Airlines CHI EYW Thu, Aug 29 - Thu, Sep 5 $476
airline logo US Airways CHI EYW Wed, Feb 5 - Wed, Feb 12 $578