Flights from Chicago to Key West

Selected fares from Chicago to Key West

Departure
Arrival
Travel dates
Round-trip

Departure:

CHI

Arrival:

EYW

Travel dates

Tue, Dec 8 - Wed, Dec 16

Round-trip

Departure:

CHI

Arrival:

EYW

Travel dates

Sun, Oct 18 - Tue, Oct 27

Round-trip

Departure:

CHI

Arrival:

EYW

Travel dates

Fri, Oct 2 - Tue, Oct 6

Round-trip

Departure:

CHI

Arrival:

EYW

Travel dates

Sat, Oct 31 - Wed, Nov 4

Round-trip

Departure:

CHI

Arrival:

EYW

Travel dates

Thu, Feb 25 - Sun, Feb 28

Round-trip

September 2015
Sun
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Sat
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Sun, Sep 20
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Wed, Sep 23
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Thu, Sep 24
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Fri, Sep 25
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Sat, Sep 26
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Sun, Sep 27
28
Mon, Sep 28
29
Tue, Sep 29

Leaving Tue, Sep 29

Returning options:

30
Wed, Sep 30

= 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

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Carriers

Airports in Key West FL, US

Key West
  • 1

    Key West International (EYW)

    Distance from City Center: 2.9 miles

    Carriers

  • 2

    Miami International Airport (MIA)

    Distance from City Center: 128.3 miles

    Carriers

  

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Featured Key West Airport Hotels

http://www.tnetnoc.comnull
3675 South Roosevelt Blvd Map
4.4 / 5 37 reviews
From
$339

...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
$339
http://www.tnetnoc.com/hotelphotos/131/16131/2631759-Doubletree-Grand-Key-Resort-Hotel-Exterior-2-LP.jpg
3990 S. Roosevelt Blvd Map
4.0 / 5 143 reviews
  • Rate includes a $50 USD daily hotel credit
  • Rate includes a $50 USD daily hotel credit
From
$179

The Green Lodging-certified Doubletree Grand Key Resort hotel sits near the airport on the eastern side of Key West, and while it's set apart from the main action on Duval Street and Mallory... More

From
$179
http://www.tnetnoc.com/hotelphotos/451/46451/69481597-Sheraton-Suites-Key-West-Hotel-Exterior-1-LP.jpg
2001 South Roosevelt Boulevard Map
4.2 / 5 134 reviews
  • Save 40% on your stay
  • Save 40% on your stay
From
$209

...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
$209
http://www.tnetnoc.com/hotelphotos/419/294419/2241284-Coconut-Mallory-Resort-and-Marina-by-Kees-Vacations-Hotel-Exterior-1-LP.jpg
1445 S. Roosevelt Blvd. Map
3.8 / 5 48 reviews
From
$165

...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
$165
http://www.tnetnoc.com/hotelphotos/151/765151/2241284-Ibis-Bay-Resort-Hotel-Exterior-1-LP.jpg
3101 North Roosevelt Blvd Map
3.3 / 5 71 reviews
From
$169

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

From
$169

September

Cheapest weekend flights in September from Chicago to Key West

Leave
Fri, Sep 18
Chicago
(ORD)
Key West
(EYW)
American Airlines
American Airlines
Return
Mon, Sep 21
Key West
(EYW)
Chicago
(ORD)
American Airlines
American Airlines
Earn $4.37

Lowest roundtrip airfare in September from Chicago to Key West

Leave
Tue, Sep 29
Chicago
(ORD)
Key West
(EYW)
United Airlines
United Airlines
Return
Tue, Oct 13
Key West
(EYW)
Chicago
(ORD)
United Airlines
United Airlines
Earn $3.94

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

Leave
Fri, Sep 11
Chicago
(MDW)
Key West
(EYW)
Delta Air Lines
Delta Air Lines
Return
Fri, Sep 18
Key West
(EYW)
Chicago
(MDW)
Delta Air Lines
Delta Air Lines
Earn $4.58

October

Lowest roundtrip airfare in October from Chicago to Key West

Leave
Fri, Oct 2
Chicago
(ORD)
Key West
(EYW)
United Airlines
United Airlines
Return
Tue, Oct 6
Key West
(EYW)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.19

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

Leave
Fri, Oct 9
Chicago
(ORD)
Key West
(EYW)
US Airways
US Airways
Return
Fri, Oct 16
Key West
(EYW)
Chicago
(ORD)
US Airways
US Airways
Earn $5.06

November

Cheapest weekend flights in November from Chicago to Key West

Leave
Fri, Nov 13
Chicago
(ORD)
Key West
(EYW)
American Airlines
American Airlines
Return
Mon, Nov 16
Key West
(EYW)
Chicago
(ORD)
American Airlines
American Airlines
Earn $5.43

Lowest roundtrip airfare in November from Chicago to Key West

Leave
Tue, Nov 10
Chicago
(ORD)
Key West
(EYW)
United Airlines
United Airlines
Return
Fri, Nov 13
Key West
(EYW)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.03

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

Leave
Sat, Nov 28
Chicago
(ORD)
Key West
(EYW)
jetBlue
jetBlue
Return
Sat, Dec 5
Key West
(EYW)
Chicago
(ORD)
jetBlue
jetBlue
Earn $7.97

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, Aug 30, 2015

Departing   Arriving Carrier Flight # Aircraft Flight time

Departing

MDW 6:00 AM

Arriving

EYW 11:38 AM
Delta Air Lines/Delta Air Lines
DL2030/DL1355
Aircraft 717/73W Flight time 4hr 38min

Departing

ORD 6:00 AM

Arriving

EYW 11:38 AM
Delta Air Lines/Delta Air Lines
DL977/DL1355
Aircraft M90/73W Flight time 4hr 38min

Departing

ORD 5:00 AM

Arriving

EYW 11:44 AM
American Airlines/American Airlines
AA2458/AA3352
Aircraft 738/ER4 Flight time 5hr 44min

Departing

ORD 5:00 AM

Arriving

EYW 11:44 AM
American Airlines/US Airways
AA2458/US3352
Aircraft 738/ER4 Flight time 5hr 44min

Departing

ORD 6:00 AM

Arriving

EYW 11:44 AM
American Airlines/American Airlines
AA1411/AA3352
Aircraft 738/ER4 Flight time 4hr 44min

Departing

ORD 6:00 AM

Arriving

EYW 11:44 AM
American Airlines/US Airways
AA1411/US3352
Aircraft 738/ER4 Flight time 4hr 44min

Departing

ORD 5:00 AM

Arriving

EYW 11:44 AM
US Airways/American Airlines
US2458/AA3352
Aircraft 738/ER4 Flight time 5hr 44min

Departing

ORD 5:00 AM

Arriving

EYW 11:44 AM
US Airways/US Airways
US2458/US3352
Aircraft 738/ER4 Flight time 5hr 44min

Departing

ORD 6:00 AM

Arriving

EYW 11:44 AM
US Airways/American Airlines
US1411/AA3352
Aircraft 738/ER4 Flight time 4hr 44min

Departing

ORD 6:00 AM

Arriving

EYW 11:44 AM
US Airways/US Airways
US1411/US3352
Aircraft 738/ER4 Flight time 4hr 44min

Departing

ORD 6:00 AM

Arriving

EYW 12:22 PM
United Airlines/United Airlines
UA1417/UA3116
Aircraft 739/SF3 Flight time 5hr 22min

Departing

ORD 6:00 AM

Arriving

EYW 1:21 PM
United Airlines/Silver Airways
UA1417/3M109
Aircraft 739/SF3 Flight time 6hr 21min

Departing

ORD 6:53 AM

Arriving

EYW 1:59 PM
American Airlines/Delta Air Lines
AA4352/DL4976
Aircraft E75/CR7 Flight time 6hr 6min