23 days in Chicago, Miami & New York City Itinerary

23 days in Chicago, Miami & New York City Itinerary

Created using Inspirock United States trip planner

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Chicago
— 5 nights
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Miami
— 7 nights
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New York City
— 7 nights
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Chicago

— 5 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Give yourself a bit of retail therapy at The Magnificent Mile and Adagio Teas. Visiting Little Red Schoolhouse and Whihala Beach will get you outdoors. Change things up with a short trip to Prairie States Winery in Genoa (about 1h 20 min away). There's lots more to do: explore the world behind art at The Art Institute of Chicago, meet the residents at Lincoln Park Zoo, stroll around Millennium Park, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

For other places to visit, traveler tips, and other tourist information, go to the Chicago route builder.

Riyadh, Saudi Arabia to Chicago is an approximately 20.5-hour flight. The time zone changes from Arabian Standard Time (AST) to Central Standard Time (CST), which is usually a -9 hour difference. Expect much colder temperatures when traveling from Riyadh in May; daily highs in Chicago reach 25°C and lows reach 13°C. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Miami.

Things to do in Chicago

Parks · Museums · Childrens Museums · Outdoors

Side Trips

Miami

— 7 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Take a break from the city and head to South Beach and Haulover Beach Park. You'll get in some beach time at John D. MacArthur Beach State Park and Peanut Island Park. Change things up with these side-trips from Miami: Fort Lauderdale (Fort Lauderdale Beach & Las Olas Beach), Everglades National Park (Shark Valley Visitor Center, Gumbo Limbo Trail, &more) and Hollywood Beach (in Hollywood). There's much more to do: take a stroll through Lincoln Road, get a taste of the local shopping with Worth Avenue, don't miss a visit to Collins Avenue, and stop by Coast Boutique.

To see photos, other places to visit, and tourist information, refer to the Miami trip builder app.

Traveling by flight from Chicago to Miami takes 6 hours. Alternatively, you can drive; or do a combination of bus and subway. Traveling from Chicago to Miami, you'll lose 1 hour due to the time zone difference. Traveling from Chicago in May, you will find days in Miami are a bit warmer (36°C), and nights are warmer (27°C). Cap off your sightseeing on the 14th (Tue) early enough to travel to New York City.

Things to do in Miami

Parks · Outdoors · Beaches · Shopping

Side Trips

New York City

— 7 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Your cultural itinerary includes sights like Times Square and 9/11 Memorial. Head to Fifth Avenue and Shopping Girlfriend NYCfor some retail therapy. Go for a jaunt from New York City to Patchogue to see Fire Island National Seashore about 1h 20 min away. There's much more to do: go for a walk through Central Park, look for gifts at Tiffany & Co., pause for some photo ops at Statue of Liberty National Monument, and admire the masterpieces at The Museum of Modern Art (MoMA).

To see maps, photos, where to stay, and other tourist information, use the New York City travel route planner.

Traveling by flight from Miami to New York City takes 6 hours. Alternatively, you can drive; or take a bus. Expect little chillier temperatures when traveling from Miami in May; daily highs in New York City reach 24°C and lows reach 15°C. Wrap up your sightseeing on the 22nd (Wed) to allow time to travel back home.

Things to do in New York City

Neighborhoods · Shopping · Museums · Parks

Side Trip