Vacation Packages w/ Airfare, Hotel & Tours to Key West from ORD - Chicago

Thinking about traveling to Key West from Chicago? Key West is a vibrant and eclectic city located at the southernmost tip of Florida. Known for its laid-back atmosphere, stunning sunsets, and rich history, Key West offers a unique blend of culture and natural beauty. From exploring the charming str... read more

Florida Keys Island Hopping Adventure

The Florida Keys are one of the best tropical destinations in the US that make you feel like you're in the Caribbean – and with this Florida vacation, you'll get to stay domestic while exploring Key Largo, Marathon, and Key West. You'll have the freedom of your own included rental car to beach-hop, sunbathe, and relax however you please while staying at upscale accommodations.

From
ORD $1,828 * Per Person

6+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, hotels, and automatic rental car. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Key West Getaway

Make your escape to balmy Key West. Your 4, 5, or 6-night stay will give you the time you need to unwind at the beach, explore the town, and sample the local fare. With round-trip airfare, accommodations, and a tour of the Old Town included, this package has everything you need for a stress-free vacation.

From
ORD $1,262 * Per Person

4+ Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, hotel and tour. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Road Trip: Key West

Make your escape to balmy Key West. Your 4, 5, or 6-night stay will give you the time you need to unwind at the beach, explore the town, and sample the local fare. With accommodations and a tour of the Old Town included, this package has everything you need for a stress-free vacation.

From
ORD $825 * Per Person

4+ Nights

2 People

* Vacation is per person, based on 2 travelers. Includes all accommodation, tour. Airfare and car rental are not included. Rates are available for 1 to 9 travelers.

Miami & Key West

Skip the parks and soak up some sun and relaxation in beautiful Florida! This trip will take you to Miami, with its world-famous beaches and nightlife, as well as Key West, the southernmost point in the continental U.S. Enjoy the pastel-hued houses, coral reefs, and island life at it's best before returning to Miami.

From
ORD $1,529 * Per Person

6 Nights

2 People

* Vacation is round-trip, per person, based on 2 travelers from Chicago Ohare Intl (ORD). Includes air, airport taxes, automatic rental car, and hotel. Additional baggage charges may apply. Rates are available for 1 to 9 travelers.

Road Trip: Key Largo, Marathon & Key West

Experience the allure of the Florida Keys, a top-tier tropical paradise in the United States, where the ambiance is reminiscent of the Caribbean. Embark on a remarkable Florida vacation, immersing yourself in the captivating wonders of Key Largo, Marathon, and Key West. Delight in the independence afforded by your personal car, allowing you to effortlessly hop between pristine beaches, bask in the sun's warm embrace, and unwind at luxurious accommodations tailored to your every desire.

From
ORD $1,050 * Per Person

6+ Nights

2 People

* Vacation is per person, based on 2 travelers. Includes all accommodation. Airfare and car rental are not included. Rates are available for 1 to 9 travelers.

Road Trip: Miami & Key West

From
ORD $976 * Per Person

6 Nights

2 People

* Vacation is per person, based on 2 travelers. Includes all accommodation. Airfare and car rental are not included. Rates are available for 1 to 9 travelers.