Selected fares from Chicago to Florida Keys

Wed, Jan 18 - Wed, Jan 25
ORD
O'Hare Intl.
EYW
Key West Intl.
$290.53

roundtrip

Tue, Jan 31 - Tue, Feb 7
MDW
Midway Intl.
EYW
Key West Intl.
$290.54

roundtrip

Sat, Feb 18 - Sat, Feb 25
ORD
O'Hare Intl.
EYW
Key West Intl.
$600.20

roundtrip

Wed, Oct 12 - Wed, Oct 19
ORD
O'Hare Intl.
EYW
Key West Intl.
$322.71

roundtrip

Thu, Feb 9 - Mon, Feb 13
ORD
O'Hare Intl.
EYW
Key West Intl.
$397.20

roundtrip

Sat, Mar 25 - Thu, Mar 30
ORD
O'Hare Intl.
EYW
Key West Intl.
$467.33

roundtrip

Tue, Jan 31 - Tue, Feb 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$290.20

roundtrip

Tue, Nov 29 - Sat, Dec 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$308.53

roundtrip

Wed, Jan 18 - Wed, Jan 25
ORD
O'Hare Intl.
EYW
Key West Intl.
$308.53

roundtrip

Tue, Jan 31 - Tue, Feb 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$308.11

roundtrip

Sat, Dec 3 - Thu, Dec 8
ORD
O'Hare Intl.
EYW
Key West Intl.
$308.53

roundtrip

Wed, Oct 12 - Wed, Oct 19
ORD
O'Hare Intl.
EYW
Key West Intl.
$310.87

roundtrip

Sat, Oct 29 - Fri, Nov 4
ORD
O'Hare Intl.
EYW
Key West Intl.
$317.66

roundtrip

Tue, Nov 29 - Sat, Dec 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$323.97

roundtrip

Tue, Nov 29 - Tue, Dec 6
ORD
O'Hare Intl.
EYW
Key West Intl.
$323.70

roundtrip

Wed, Jan 18 - Wed, Jan 25
ORD
O'Hare Intl.
EYW
Key West Intl.
$325.20

roundtrip

Fri, Nov 11 - Fri, Nov 18
MDW
Midway Intl.
EYW
Key West Intl.
$321.71

roundtrip

Sun, Jan 8 - Sat, Jan 14
ORD
O'Hare Intl.
EYW
Key West Intl.
$323.97

roundtrip

Thu, Dec 8 - Sun, Dec 11
ORD
O'Hare Intl.
EYW
Key West Intl.
$323.97

roundtrip

Fri, Dec 16 - Sun, Dec 18
ORD
O'Hare Intl.
EYW
Key West Intl.
$340.49

roundtrip

Thu, Dec 8 - Sun, Dec 11
ORD
O'Hare Intl.
EYW
Key West Intl.
$323.97

roundtrip

Mon, Nov 28 - Mon, Dec 5
ORD
O'Hare Intl.
EYW
Key West Intl.
$349.65

roundtrip

Tue, Nov 29 - Sat, Dec 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$348.55

roundtrip

Tue, Nov 29 - Sat, Dec 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$352.21

roundtrip

Wed, Oct 12 - Wed, Oct 19
ORD
O'Hare Intl.
EYW
Key West Intl.
$352.71

roundtrip

Wed, Oct 12 - Wed, Oct 19
ORD
O'Hare Intl.
EYW
Key West Intl.
$353.71

roundtrip

Wed, Oct 12 - Wed, Oct 19
ORD
O'Hare Intl.
EYW
Key West Intl.
$355.21

roundtrip

Sat, Jan 14 - Tue, Jan 17
ORD
O'Hare Intl.
EYW
Key West Intl.
$360.04

roundtrip

Wed, Feb 15 - Thu, Feb 23
ORD
O'Hare Intl.
EYW
Key West Intl.
$361.20

roundtrip

Fri, Nov 4 - Thu, Nov 10
ORD
O'Hare Intl.
EYW
Key West Intl.
$362.71

roundtrip

Fri, Nov 4 - Thu, Nov 10
ORD
O'Hare Intl.
EYW
Key West Intl.
$363.71

roundtrip

Flights from Chicago

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.

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Save more with Florida Keys Flight + Hotel packages

Hotels in Florida Keys

See all 206 Hotels in Florida Keys
The Inn at Key West
The Inn at Key West
3420 N Roosevelt Blvd, Key West
3.5 out of 5.0
4.1 out of 5 (10 reviews)

Located within minutes of Old Town, the Ernest Hemingway Home & Museum, Mallory Square, Duval Street shops, restaurants, and nightlife.

$129

$129
Lime Tree Bay Resort
Lime Tree Bay Resort
68500 Overseas Hwy, Long Key
3.5 out of 5.0
3.8 out of 5 (11 reviews)

This waterfront resort sits on 1/4 mile of tropical waterfront in the heart of the Florida Keys. Close to Long Key State Park and Dolphin Research Center.

$99

$99
Southernmost Beach Resort
Southernmost Beach Resort
508 South St, Key West
4.0 out of 5.0
4.5 out of 5 (141 reviews)

This Key West historical district hotel is 2 blocks from Southernmost Point. Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters ...

$199

$199
Hilton Key Largo Resort
Hilton Key Largo Resort
97000 Overseas Hwy, Key Largo
3.5 out of 5.0
3.7 out of 5 (111 reviews)

This island resort--with a white-sand beach on the Gulf of Mexico--has a quarter-mile-long boardwalk trail winding through it 12 acres of dense foliage and rare ...

$169

$169
Sheraton Suites Key West
Sheraton Suites Key West
2001 S Roosevelt Blvd, Key West
3.5 out of 5.0
4.2 out of 5 (126 reviews)

This casual resort is located three miles from the museums and boisterous streets of Old Town, and provides easy access to water sports at the popular Smathers ...

$186

$186
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West
3.5 out of 5.0
4.1 out of 5 (137 reviews)

Located on the quieter side of Key West, this tropical-style resort offers complimentary scheduled shuttle service to Duval Street as well as shuttle service ...

$151

$151
Marina Del Mar Resort and Marina
Marina Del Mar Resort and Marina
527 Caribbean Drive, Key Largo
2.5 out of 5.0
3.4 out of 5 (153 reviews)

This resort and marina is in the heart of Key Largo, near watersports and dive businesses.

$119

$119
Parrot Key Hotel & Resort
Parrot Key Hotel & Resort
2801 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.0 out of 5 (161 reviews)

Situated on the waterfront, this romantic resort is within 3 mi (5 km) of Smathers Beach, Ernest Hemingway Home and Museum, and Audubon House and Tropical Gardens. ...

$143

$143
Casa Marina Resort - A Waldorf Astoria Resort
Casa Marina Resort - A Waldorf Astoria Resort
1500 Reynolds Street, Key West
4.0 out of 5.0
4.2 out of 5 (221 reviews)

Looking out over the Straits of Florida towards Cuba, this upscale resort places guests a 3-minute drive from downtown Key West. The Ernest Hemingway Home & ...

$289

$289
Seashell Motel & Key West Hostel
Seashell Motel & Key West Hostel
718 South Street, Key West
1.5 out of 5.0
1.0 out of 5 (1 reviews)

Located in the heart of Key West, this hostel is within a 15-minute walk of South Beach and Ernest Hemingway Home and Museum. Audubon House and Tropical Gardens ...

$88

$88

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.