Experience The New Parrot Key

Now Accepting New Reservations Learn More

Stay More, Save More
Up to 30% Off 2018 Stays

The longer you stay, the more you save Learn More

Join IC Local!
Join IC Local!

The more you stay, the more you get rewarded with local perks. Join Now

Push to Chat
Push to Chat

Click to chat with an agent now. Push to Chat

Planning Guide

View travel planning tips or call 855-318-2766. Learn More

WaveRunner Package
Save $75: WaveRunner Package

Save $75 on our 1.5 hour tour around Key West! Learn More

Watersports Discounts
Watersports Discounts

View our "Super Discounts" on watersports activities! Learn More

Free Shuttle

to Duval Street and Smathers Beach Learn More

Fly Direct From Chicago O'Hare to Key West International Airport

Trade the Chicago Winter for White Sand in Key West at Parrot Key Resort

Escape the Chicago winter and transport yourself to paradise with a non-stop, direct flight from Chicago O'Hare International Airport (ORD) to Key West International (EYW). Plan a long weekend break or a last-minute vacation to the unique tropical island city of Key West and enjoy direct seasonal flight service with United Airlines, which launches on January 7 for travel dates through April 29, 2017.

Direct weekly flights from Chicago to Key West depart Chicago O’Hare Airport every Saturday at 10:40am, so you can arrive in our subtropical paradise by the afternoon and unwind poolside to soak up the winter sunshine. From Key West International, Parrot Key Resort can be easily reached within a ten minute drive, and there are a number of local car rental companies available as well as taxis and shuttles to help you reach the resort.

Chicago Residents: Winter Escape Sale - Save up to 25% >

Call 866-748-6020 to Speak with an Onsite Vacation Planner

About Parrot Key Resort

Tucked away just minutes away from the historic Old Town, Parrot Key Resort is an idyllic island hideaway that defines Key West’s carefree lifestyle. Set among five acres of award-winning tropical gardens, Parrot Key offers simple luxury, four sparkling pools and the most spacious rooms and suites in Key West, all perfectly presented in a calm waterfront oasis. Peaceful and secluded, yet within an easy stroll away from the upbeat energy of Key West.

Parrot Key Resort’s central location offers great convenience to explore Key West’s treasure trove of attractions, restaurants, boutiques, museums, beaches and night life. The resort also operates a complimentary shuttle between the hotel and Smather’s Beach or Downtown Key West.

Our guestrooms, suites and three-bedroom villas are all surrounded by the natural beauty of the Florida Keys with a choice of waterfront views or the spectacular scenery of towering palm trees. For poolside relaxation, unwind at Café Blue where casual island cuisine is served at breakfast and lunch, with a range of refreshing island drinks and delicious snacks served throughout the day in a 100% smoke-free environment.

You will head back to Chicago feeling refreshed, recharged and sun-kissed after your easy winter getaway to the Florida Keys which are quick to reach, yet feel a million miles away. For more information on flights between Chicago and Key West, visit