22 days in Illinois & Florida Itinerary

22 days in Illinois & Florida Itinerary

Created using Inspirock United States trip planner
Make it your trip
Fly
1
Chicago
— 4 nights
Fly
2
Orlando
— 4 nights
Fly
3
Key West
— 4 nights
Drive
4
Big Pine Key
— 2 nights
Drive
5
Key Largo
— 2 nights
Drive
6
Miami Beach
— 4 nights
Fly

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Chicago — 4 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: explore the world behind art at The Art Institute of Chicago, admire the striking features of 360 Chicago Observation Deck, learn about wildlife with up-close encounters at Lincoln Park Zoo, and laugh and play at Fox in a Box Chicago.

For ratings, traveler tips, reviews, and more tourist information, go to the Chicago attractions planner.

Bangkok, Thailand to Chicago is an approximately 23-hour flight. The time zone changes from Indochina Time to Central Standard Time, which is usually a -13 hour difference. Expect colder temperatures when traveling from Bangkok in February; daily highs in Chicago reach 2°C and lows reach -7°C. Finish your sightseeing early on the 7th (Mon) to allow enough time to fly to Orlando.
Museums · Childrens Museums · Parks · Zoos & Aquariums
Side Trip

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.
When in Orlando, make a side trip to see Boat Tours & Water Sports in Saint Cloud, approximately Saint Cloud away. Have a day of magic on the 9th (Wed) at Walt Disney World Resort. Pack the 8th (Tue) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: find something for the whole family at Universal Orlando Resort, explore the world behind art at Charles Hosmer Morse Museum of American Art, and discover the magic at Magic Kingdom Park.

To find traveler tips, maps, reviews, and more tourist information, read Orlando online trip itinerary builder.

You can fly from Chicago to Orlando in 4.5 hours. Other options are to drive; or take a bus. The time zone difference when traveling from Chicago to Orlando is 1 hour. Prepare for much hotter weather when traveling from Chicago in February: high temperatures in Orlando hover around 28°C and lows are around 15°C. Finish your sightseeing early on the 11th (Fri) so you can fly to Key West.
Theme Parks · Outdoors · Tours · Museums
Side Trips

Key West — 4 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.
Key West is known for sightseeing, museums, and adventure. Your trip includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, steep yourself in history at Truman Little White House, don't miss a visit to Duval Street, and cruise along The Overseas Highway.

For maps, other places to visit, and other tourist information, refer to the Key West day trip website.

Getting from Orlando to Key West by flight takes about 3 hours. Other options: fly; or drive; or take a bus. Traveling from Orlando in February, Key West is somewhat warmer at night with lows of 23°C. Finish up your sightseeing early on the 15th (Tue) so you can go by car to Big Pine Key.
Museums · Historic Sites · Outdoors · Parks

Big Pine Key — 2 nights

Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Start off your visit on the 16th (Wed): tour the pleasant surroundings at National Key Deer Refuge, then take in the exciting artwork at Artists in Paradise Gallery, and then take a tour by water with Boat Tours & Water Sports. Keep things going the next day: relax and rejuvenate at SpaTerre at Little Palm Island Resort and then enjoy the sand and surf at Bahia Honda State Park.

To see photos, other places to visit, traveler tips, and more tourist information, you can read our Big Pine Key travel route website.

Traveling by car from Key West to Big Pine Key takes an hour. Alternatively, you can take a shuttle; or take a bus. In February in Big Pine Key, expect temperatures between 30°C during the day and 23°C at night. Wrap up your sightseeing on the 17th (Thu) to allow time to drive to Key Largo.
Outdoors · Parks · Beaches · Shopping
Side Trips

Key Largo — 2 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.
Kick off your visit on the 18th (Fri): indulge your thirst for a good beer at Florida Keys Brewing Company, then see what you can catch with Florida Keys Flats Fishing, and then stroll through Florida Keys Wild Bird Rehabilitation Center. On the 19th (Sat), you'll have a packed day of sightseeing: get up close and personal with brilliant marine life at Island Dolphin Care, get outside with Capt. Sterling's Everglades Eco-Tours, and then see the vivid underwater world at Spiegel Grove.

To see photos, reviews, more things to do, and other tourist information, use the Key Largo road trip planning app.

Getting from Big Pine Key to Key Largo by car takes about 2 hours. Other options: take a bus. Traveling from Big Pine Key in February, you can expect nighttime temperatures to be a bit cooler in Key Largo, with lows of 19°C. Wrap up your sightseeing on the 19th (Sat) early enough to drive to Miami Beach.
Wildlife · Parks · Outdoors · Tours
Side Trip

Miami Beach — 4 nights

Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Change things up with these side-trips from Miami Beach: Everglades National Park (Gumbo Limbo Trail, Nike Missile Site HM-69, &more). Next up on the itinerary: cast your line with Miami Peacock Adventures - Day Tours, contemplate the long history of Barnacle State Historic Site, appreciate the extensive heritage of Lincoln Road, and admire the striking features of Art Deco Historic District.

To find more things to do, photos, ratings, and other tourist information, refer to the Miami Beach trip itinerary builder app.

Traveling by car from Key Largo to Miami Beach takes 1.5 hours. Alternatively, you can take a bus; or take a bus. In February, daily temperatures in Miami Beach can reach 30°C, while at night they dip to 21°C. You'll set off for home on the 23rd (Wed).
Outdoors · Parks · Wildlife · Historic Sites
Side Trips

Illinois travel guide

4.3
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.

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.