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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
26 27 28 29 30 31 1
2 3 4 $545 5 $757 6 $532 7 $538 8 $661
9 $616 10 $553 11 12 13 14 $532 15
16 $612 17 $476 18 $517 19 $619 20 $476 21 $486 22
23 $559 24 $480 25 $482 26 $630 27 $709 28 $602 29
30 1 2 3 4 5 6

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.

Leaving Tue, Jun 4, returning:
Sat, Jun 8
$545
Leaving Wed, Jun 5, returning:
Sun, Jun 9
$757
Leaving Thu, Jun 6, returning:
Sun, Jun 9
$570
Mon, Jun 10
$532
Leaving Fri, Jun 7, returning:
Mon, Jun 10
$644
Sat, Jun 15
$538
Leaving Sat, Jun 8, returning:
Sat, Jun 15
$661
Leaving Sun, Jun 9, returning:
Sat, Jun 15
$616
Leaving Mon, Jun 10, returning:
Sat, Jun 15
$583
Tue, Jun 18
$553
Leaving Fri, Jun 14, returning:
Mon, Jun 17
$532
Tue, Jun 18
$532
Leaving Sun, Jun 16, returning:
Sat, Jun 22
$612
Leaving Mon, Jun 17, returning:
Thu, Jun 20
$476
Sat, Jun 22
$569
Leaving Tue, Jun 18, returning:
Fri, Jun 21
$517
Sat, Jun 22
$543
Sun, Jun 23
$590
Leaving Wed, Jun 19, returning:
Sun, Jun 23
$619
Mon, Jun 24
$652
Leaving Thu, Jun 20, returning:
Thu, Jun 27
$583
Sat, Jun 29
$476
Leaving Fri, Jun 21, returning:
Tue, Jun 25
$486
Leaving Sun, Jun 23, returning:
Sat, Jun 29
$559
Sun, Jun 30
$606
Leaving Mon, Jun 24, returning:
Fri, Jun 28
$561
Sun, Jun 30
$642
Mon, Jul 1
$480
Leaving Tue, Jun 25, returning:
Mon, Jul 1
$482
Leaving Wed, Jun 26, returning:
Fri, Jun 28
$630
Sun, Jun 30
$675
Leaving Thu, Jun 27, returning:
Sun, Jun 30
$709
Leaving Fri, Jun 28, returning:
Sun, Jun 30
$602
Sun, Jul 7
$626
June

Cheapest weekend flights in June from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jun 14 Chicago (ORD) Key West (EYW) Delta Air Lines $532
Return Mon, Jun 17 Key West (EYW) Chicago (ORD) Delta Air Lines

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 Mon, Jun 24 Chicago (ORD) Key West (EYW) United Airlines $480
Return Mon, Jul 1 Key West (EYW) Chicago (ORD) United Airlines
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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 $498
Return Sun, Jul 21 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 9 Chicago (ORD) Key West (EYW) United Airlines $482
Return Fri, Jul 12 Key West (EYW) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jul 10 Chicago (ORD) Key West (EYW) United Airlines $486
Return Wed, Jul 17 Key West (EYW) Chicago (ORD) United Airlines
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) Delta Air Lines $476
Return Mon, Aug 26 Key West (EYW) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in August from Chicago to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 16 Chicago (ORD) Key West (EYW) United Airlines $473
Return Mon, Aug 26 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 3 Chicago (ORD) Key West (EYW) United Airlines $502
Return Sat, Aug 10 Key West (EYW) Chicago (ORD) United Airlines
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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

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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 airline tickets from Chicago to Key West

Airline Departure Arrival Travel dates Round-trip
Delta Airlines Delta Air Lines CHI EYW Fri, Aug 23 - Mon, Aug 26 $476
airline logo American Airlines CHI EYW Fri, May 31 - Tue, Jun 4 $476
airline logo United Airlines CHI EYW Fri, Jun 21 - Tue, Jun 25 $486
airline logo US Airways CHI EYW Sat, Feb 1 - Tue, Feb 4 $562