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 Ground Zero Museum Workshop. 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). And it doesn't end there: make a trip to Central Park, go for a charming ride with a horse-drawn carriage tour, contemplate in the serene atmosphere at The Met Cloisters, and see the interesting displays at New York Public Library.

To find reviews, traveler tips, more things to do, and other tourist information, you can read our New York City trip itinerary maker app.

Sao Paulo, Brazil to New York City is an approximately 13-hour flight. The time zone changes from Brasilia Standard Time (BRT) to Eastern Standard Time (EST), which is usually a -2 hour difference. In July, New York City is a bit warmer than Sao Paulo - with highs of 35°C and lows of 26°C. Finish up your sightseeing early on the 14th (Wed) so you can catch the flight 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 Lakefront Trail. Explore the numerous day-trip ideas around Chicago: Allen Park (in Ottawa), Starved Rock State Park (in Utica) and LaSalle Rotary Park (in LaSalle). There's still lots to do: explore the activities along Chicago River, take in panoramic vistas at 360 Chicago Observation Deck, admire the local landmark of Crown Fountain, and learn more about the world around you at Field Museum.

To see traveler tips, ratings, photos, and tourist information, you can read our Chicago trip planner.

You can fly from New York City to Chicago in 4 hours. Other options are to drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Traveling from New York City in July, expect slightly colder with lows of 22°C in Chicago. Wrap up your sightseeing on the 21st (Wed) to allow time to fly to Orlando.

Things to do in Chicago

Parks · Museums · Childrens Museums · Outdoors

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 Disney’s Blizzard Beach Water Park. You'll find plenty of places to visit near Orlando: Fishing Charters & Tours (in Port Canaveral), Daytona Beach (Daytona International Speedway, Beach at Daytona Beach, &more) and Cherie Down Park (in Cape Canaveral). Pack the 27th (Tue) with family-friendly diversions at Universal's Islands of Adventure. Next up on the itinerary: take in the architecture and atmosphere at Basilica of the National Shrine of Mary, Queen of the Universe, steep yourself in history at Stetson Mansion, examine the collection at Madame Tussauds Orlando, and enjoy some diversion at Machine Gun America.

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 4.5 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 fly back home.

Things to do in Orlando

Theme Parks · Outdoors · Tours · Historic Sites

Side Trips

Find places to stay Jul 21 — 31: