12 days in Chicago & U.S. Virgin Islands Itinerary

12 days in Chicago & U.S. Virgin Islands Itinerary

Created using Inspirock trip itinerary planner

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Chicago, United States
— 3 nights
Fly to Charlotte Amalie, Ferry to Cruz Bay
Cruz Bay, U.S. Virgin Islands
— 3 nights
East End, U.S. Virgin Islands
— 2 nights
St. Croix, U.S. Virgin Islands
— 3 nights


Chicago, United States

— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Lakefront Trail and Starved Rock State Park. You'll explore the less-touristy side of things at Silver Beach County Park and Matthiessen State Park. Explore Chicago's surroundings by going to Allen Park (in Ottawa), Whirlpool Compass Fountain (in Saint Joseph) and Indiana Dunes State Park (in Chesterton). The adventure continues: appreciate the extensive heritage of Chicago Riverwalk, take a stroll through The Loop, explore the activities along Chicago River, and admire the local landmark of Buckingham Fountain.

To find other places to visit, more things to do, photos, and more tourist information, you can read our Chicago travel itinerary planner.

New York City to Chicago is an approximately 4-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. May in Chicago sees daily highs of 71°F and lows of 52°F at night. On the 16th (Sun), wrap the sightseeing up by early afternoon so you can travel to Cruz Bay.

Things to do in Chicago

Parks · Nature · Outdoors · Trails

Side Trips

Cruz Bay, U.S. Virgin Islands

— 3 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Discover out-of-the-way places like Cinnamon Bay Beach and Hawksnest Beach. Escape the urban bustle at Scuba & Snorkeling and Salt Pond Bay. Next up on the itinerary: tour the pleasant surroundings at Ram Head Trail, stop by Bamboo Studio, see the vivid underwater world at Honeymoon Beach, and contemplate the waterfront views at Francis Bay.

To find where to stay, photos, ratings, and more tourist information, go to the Cruz Bay itinerary planning site.

Getting from Chicago to Cruz Bay by combination of flight and ferry takes about 9 hours. You'll lose 2 hours traveling from Chicago to Cruz Bay due to the time zone difference. Traveling from Chicago in May, you will find days in Cruz Bay are somewhat warmer (87°F), and nights are much warmer (77°F). Finish your sightseeing early on the 19th (Wed) so you can ride a ferry to East End.

Things to do in Cruz Bay

Outdoors · Parks · Beaches · Wildlife

Side Trips

East End, U.S. Virgin Islands

— 2 nights
On the 20th (Thu), look for gifts at Ballerina Jewelers, kick back and relax at Lindqvist Beach, and then kick back and relax at Sapphire Beach. On the next day, relax and rejuvenate at some of the best spas, then get a dose of the wild on The VI Cat, and then tour the pleasant surroundings at Morningstar Beach.

To see where to stay, ratings, maps, and other tourist information, use the East End trip itinerary planner.

Getting from Cruz Bay to East End by ferry takes about an hour. In May, daily temperatures in East End can reach 87°F, while at night they dip to 77°F. Wrap up your sightseeing on the 21st (Fri) to allow time to fly to St. Croix.

Things to do in East End

Outdoors · Beaches · Parks · Tours

Side Trips

St. Croix, U.S. Virgin Islands

— 3 nights

Twin City

The largest of the U.S. Virgin Islands, St.
Step off the beaten path and head to St. Croix Ultimate Bluewater Adventures (SCUBA), Inc. and Buck Island Reef National Monument. Visit Rhythms at Rainbow Beach and Rainbow Beach for some beach relaxation. And it doesn't end there: pause for some photo ops at Point Udall, steep yourself in history at Fort Christiansvaern, stop by Baci Duty Free, and enjoy the sand and surf at Cane Bay.

Use Inspirock's suggestions to plan your St. Croix trip and find the best activities and attractions for your vacation.

Getting from East End to St. Croix by flight takes about 2.5 hours. Other options: do a combination of car and ferry. May in St. Croix sees daily highs of 87°F and lows of 76°F at night. On the 24th (Mon), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in St. Croix

Parks · Outdoors · Beaches · Wildlife

U.S. Virgin Islands travel guide

Beaches · Gift & Specialty Shops · Scuba & Snorkeling
America's Paradise
Three main and a number of minor islands that make up U.S. Virgin Islands treat visitors to a blend of historical sites and picture-perfect beaches. Though officially American territory--nicknamed "America's Paradise"--these islands boast a mix of cultures that make for culturally enriching vacations. A no-passport-required status makes holidays in U.S. Virgin Islands extremely popular with American tourists, who flock to this tropical heaven to enjoy scenic beaches, outdoor activities, and tasty local food. The islands are also a duty-free shopping destination, which also makes them appealing to shopaholics from across the world.