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

Make it your trip
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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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New York City

— 13 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.
Eschew the tourist crowds and head to Speed Boats Tours and Food Tours. Explore New York City's surroundings by going to Philadelphia (Philadelphia Museum of Art, Eastern State Penitentiary, &more) and Hyde Park (Vanderbilt Mansion National Historic Site & Franklin D. Roosevelt Presidential Library and Museum). The adventure continues: don't miss a visit to Central Park, take in the architecture and atmosphere at St. Patrick's Cathedral, contemplate in the serene atmosphere at The Met Cloisters, 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:

Chicago

— 7 nights

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 Chicago Riverwalk and Lake Michigan. Explore the numerous day-trip ideas around Chicago: Allen Park (in Ottawa), Starved Rock State Park (in Utica) and LaSalle Rotary Park (in LaSalle). 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 ponder the design of Crown Fountain.

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 5.5 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:

Orlando

— 10 nights

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 Disney's Typhoon Lagoon Water Park and Fishing Charters & Tours. You'll find plenty of places to visit near Orlando: Daytona Beach (Daytona International Speedway, Beach at Daytona Beach, &more), Cherie Down Park (in Cape Canaveral) and Stetson Mansion (in DeLand). Pack the 27th (Tue) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: discover the magic at Disney’s Blizzard Beach Water Park, make a trip to Cinderella Castle, get in on the family fun at Fun Spot America, and enjoy unforgettable views with a balloon tour.

To find traveler tips, where to stay, and tourist information, refer to the Orlando journey planner.

Getting from Chicago to Orlando by flight takes about 5.5 hours. Other options: drive; or take a bus. The time zone difference when traveling from Chicago to Orlando is 1 hour. Expect somewhat warmer temperatures when traveling from Chicago in July; daily highs in Orlando reach 38°C and lows reach 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 · Parks

Side Trips

Find places to stay Jul 21 — 31: