31 days in New York City, Chicago & Orlando Itinerary

31 days in New York City, Chicago & Orlando Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
Fly
1
New York City
— 13 nights
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2
Chicago
— 7 nights
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3
Orlando
— 10 nights
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13
nights
New York City

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.
Eschew the tourist crowds and head to Speed Boats Tours and The Met Cloisters. Explore New York City's surroundings by going to Hyde Park (Vanderbilt Mansion National Historic Site & Franklin D. Roosevelt Presidential Library and Museum) and Philadelphia (Philadelphia Museum of Art, Eastern State Penitentiary, &more). The adventure continues: don't miss a visit to Central Park, take in the local highlights with Walking tours, let your taste buds guide you at a local gastronomic tour, and examine the collection at Ground Zero Museum Workshop.

For reviews, ratings, maps, and more tourist information, read New York City online journey planner.

Sao Paulo, Brazil to New York City is an approximately 14-hour flight. Due to the time zone difference, you'll gain 2 hours traveling from Sao Paulo to New York City. Traveling from Sao Paulo in July, things will get somewhat warmer in New York City: highs are around 35°C and lows about 26°C. Finish your sightseeing early on the 14th (Wed) to allow enough time to travel to Chicago.

Things to do in New York City

Museums · Parks · Historic Sites · Tours

Side Trips

Find places to stay Jul 1 — 14:

7
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like Lake Michigan and Chicago Riverwalk. Explore the numerous day-trip ideas around Chicago: LaSalle Rotary Park (in LaSalle), Allen Park (in Ottawa) and Starved Rock State Park (in Utica). The adventure continues: explore the activities along Chicago River, grab your bike and head to Lakefront Trail, engage your brain at Museum of Science and Industry, and enjoy the scholastic atmosphere at University of Notre Dame.

To see maps, where to stay, other places to visit, and more tourist information, go to the Chicago online trip maker.

Fly from New York City to Chicago in 5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from New York City in July, plan for little chillier nights in Chicago, with lows around 22°C. Cap off your sightseeing on the 21st (Wed) early enough to travel to Orlando.

Things to do in Chicago

Parks · Museums · Outdoors · Nature

Side Trips

Find places to stay Jul 14 — 21:

10
nights
Orlando

Theme Park Capital of the World

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.
Explore hidden gems such as Fishing Charters & Tours and Disney’s Blizzard Beach Water Park. You'll find plenty of places to visit near Orlando: Cherie Down Park (in Cape Canaveral), Daytona Beach (Daytona International Speedway, Beach at Daytona Beach, &more) and Stetson Mansion (in DeLand). Pack the 27th (Tue) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: make an unforgettable trip to Disney's Typhoon Lagoon Water Park, enjoy unforgettable views with a balloon tour, make a trip to Cinderella Castle, and visit a coastal fixture at Ponce de Leon Inlet Lighthouse & Museum.

For photos, reviews, traveler tips, and tourist information, go to the Orlando driving holiday planner.

Fly from Chicago to Orlando in 5.5 hours. Alternatively, you can drive; or take a bus. You'll lose 1 hour traveling from Chicago to Orlando due to the time zone difference. Prepare for somewhat warmer weather when traveling from Chicago in July: high temperatures in Orlando hover around 38°C and lows are around 28°C. Wrap up your sightseeing on the 31st (Sat) to allow time to travel back home.

Things to do in Orlando

Theme Parks · Outdoors · Tours · Historic Sites

Side Trips

Find places to stay Jul 21 — 31: