32 days in Florida & Chicago Itinerary

32 days in Florida & Chicago Itinerary

Created using Inspirock United States trip itinerary builder
Make it your trip
Fly
1
Orlando
— 4 nights
Fly
2
Miami Beach
— 3 nights
Drive
3
Everglades National Park
— 4 nights
Fly
4
Key West
— 5 nights
Drive
5
Marathon
— 4 nights
Drive
6
Key Largo
— 3 nights
Fly
7
Chicago
— 8 nights
Fly

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Orlando — 4 nights

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Have a day of magic on the 15th (Sat) at Walt Disney World Resort. Pack the 16th (Sun) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: find something for the whole family at Universal Orlando Resort, explore the world behind art at Charles Hosmer Morse Museum of American Art, take in nature's colorful creations at Harry P. Leu Gardens, and make an unforgettable trip to Disney's Animal Kingdom Theme Park.

For where to stay, traveler tips, reviews, and tourist information, you can read our Orlando tour planner.

Reykjavik, Iceland to Orlando is an approximately 10.5-hour flight. Traveling from Reykjavik to Orlando, you'll gain 5 hours due to the time zone difference. In January, Orlando is much warmer than Reykjavik - with highs of 25°C and lows of 13°C. Finish your sightseeing early on the 18th (Tue) to allow enough time to fly to Miami Beach.
Theme Parks · Museums · Parks
Side Trip

Miami Beach — 3 nights

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Step out of Miami Beach to go to Coral Gables and see Fairchild Tropical Botanic Garden, which is approximately 38 minutes away. There's still lots to do: get to know the fascinating history of Art Deco Historic District, take a stroll through Lincoln Road, kick back and relax at South Beach, and see the interesting displays at Vizcaya Museum and Gardens.

To find traveler tips, photos, where to stay, and more tourist information, read our Miami Beach trip planner.

You can fly from Orlando to Miami Beach in 3 hours. Other options are to drive; or take a bus. Traveling from Orlando in January, things will get a bit warmer in Miami Beach: highs are around 29°C and lows about 20°C. Finish your sightseeing early on the 21st (Fri) so you can travel to Everglades National Park.
Parks · Outdoors · Museums · Neighborhoods
Side Trips

Everglades National Park — 4 nights

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
Everglades National Park is known for wildlife, trails, and parks. Your trip includes some of its best attractions: tour the pleasant surroundings at Gumbo Limbo Trail, see what you can catch with Everglades City Fishing Charters, explore the activities along Slough Slog, and contemplate the long history of Smallwood Store.

To find reviews, ratings, photos, and other tourist information, read Everglades National Park online journey maker.

The Route module can help you plan travel from Miami Beach to Everglades National Park. In January, daily temperatures in Everglades National Park can reach 29°C, while at night they dip to 22°C. Finish your sightseeing early on the 25th (Tue) so you can fly to Key West.
Parks · Wildlife · Outdoors · Nature
Side Trip

Key West — 5 nights

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Spend the 26th (Wed) exploring nature at Dry Tortugas National Park. There's much more to do: examine the collection at The Ernest Hemingway Home and Museum, get a new perspective on things with Boat Tours & Water Sports, tour the pleasant surroundings at Key West Butterfly & Nature Conservatory, and take in the exciting artwork at Alan S. Maltz Gallery.

For more things to do, maps, other places to visit, and more tourist information, read our Key West trip maker.

Traveling by flight from Everglades National Park to Key West takes 2.5 hours. Alternatively, you can take a bus; or take a bus. In January in Key West, expect temperatures between 28°C during the day and 22°C at night. Wrap up your sightseeing on the 30th (Sun) early enough to drive to Marathon.
Parks · Museums · Historic Sites · Nature

Marathon — 4 nights

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
You'll find plenty of places to visit near Marathon: SpaTerre at Little Palm Island Resort (in Little Torch Key) and Everglades National Park (in Florida City). There's much more to do: tour the pleasant surroundings at National Key Deer Refuge, snap pictures at Seven Mile Bridge, enjoy the sand and surf at Anne's Beach, and examine the collection at Crane Point Museum & Nature Center.

For more things to do, where to stay, photos, and other tourist information, you can read our Marathon online vacation planner.

You can drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 29°C in January, and nighttime lows around 22°C. Finish your sightseeing early on the 3rd (Thu) to allow enough time to drive to Key Largo.
Parks · Beaches · Outdoors · Nature
Side Trips

Key Largo — 3 nights

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Explore the numerous day-trip ideas around Key Largo: Islamorada (Indian Key State Historic Site & Lignumvitae Key Botanical State Park). There's much more to do: stroll through Florida Keys Wild Bird Rehabilitation Center, head outdoors with Capt. Sterling's Everglades Eco-Tours, meet the residents at Island Dolphin Care, and take in the dramatic natural features at Windley Key Fossil Reef Geological State Park.

For other places to visit, traveler tips, photos, and other tourist information, go to the Key Largo route maker app.

Traveling by car from Marathon to Key Largo takes 1.5 hours. Alternatively, you can take a bus. Traveling from Marathon in February, expect little chillier with lows of 19°C in Key Largo. Finish your sightseeing early on the 6th (Sun) so you can fly to Chicago.
Parks · Wildlife · Nature · Tours
Side Trip

Chicago — 8 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, learn about wildlife with up-close encounters at Lincoln Park Zoo, engage your brain at Museum of Science and Industry, and admire the landmark architecture of 360 Chicago Observation Deck.

To see other places to visit, reviews, ratings, and other tourist information, refer to the Chicago trip itinerary builder site.

You can fly from Key Largo to Chicago in 5 hours. Other options are to drive; or do a combination of shuttle and bus. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In February, Chicago is colder than Key Largo - with highs of 2°C and lows of -7°C. Finish your sightseeing early on the 14th (Mon) so you can fly back home.
Museums · Childrens Museums · Parks · Shopping
Side Trips

Florida travel guide

4.3
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.