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

Route & dates

1
New York City
— 13 nights
2
Chicago
— 7 nights
3
Orlando
— 10 nights

13
nights
New York City

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 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, wander the streets of Dumbo, explore the world behind art at The Metropolitan Museum of Art, and walk around World Trade Center's Liberty Park.

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 14-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 °C and lows of °C. Finish up your sightseeing early on the 14th (Wed) so you can travel to Chicago.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Brooklyn, Philadelphia, Hyde Park, New York Botanical Garden
Find places to stay Jul 1 — 14:
Highlights from your plan
Speed Boats Tours
Central Park ©
Central Park
Food Tours

7
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll discover tucked-away gems like Boat Tours & Water Sports and Lake Michigan. Explore the numerous day-trip ideas around Chicago: LaSalle Rotary Park (in LaSalle), Starved Rock State Park (in Utica) and Allen Park (in Ottawa). There's lots more to do: appreciate the extensive heritage of Chicago Riverwalk, explore the activities along Chicago River, indulge in some culinary diversions at a local gastronomic tour, and enjoy breathtaking views from 360 Chicago Observation Deck.

To find maps, traveler tips, more things to do, and tourist information, you can read our Chicago trip maker.

Traveling by flight from New York City to Chicago takes 5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Traveling from New York City in July, plan for little chillier nights in Chicago, with lows around °C. Cap off your sightseeing on the 21st (Wed) early enough to travel to Orlando.

Things to do in Chicago

Parks Museums Childrens Museums

Side Trips

South Bend, LaSalle Rotary Park, Starved Rock State Park, Allen Park, Lake Michigan
Find places to stay Jul 14 — 21:
Highlights from your plan
Boat Tours & Water Sports
Lake Michigan ©
Lake Michigan
Chicago Riverwalk ©
Chicago Riverwalk

10
nights
Orlando

Orlando ©
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 Basilica of the National Shrine of Mary, Queen of the Universe. You'll find plenty of places to visit near Orlando: Cherie Down Park (in Cape Canaveral), Stetson Mansion (in DeLand) and Daytona Beach (Daytona International Speedway, Beach at Daytona Beach, &more). Pack the 27th (Tue) with family-friendly diversions at Universal's Islands of Adventure. The adventure continues: make an unforgettable trip to Disney's Typhoon Lagoon Water Park, visit a coastal fixture at Ponce de Leon Inlet Lighthouse & Museum, take a memorable tour with Tours, and make a splash at Disney’s Blizzard Beach Water Park.

To see where to stay, photos, other places to visit, and tourist information, read our Orlando holiday planner.

Fly from Chicago to Orlando in 5.5 hours. Alternatively, you can drive; or take a bus. Traveling from Chicago to Orlando, you'll lose 1 hour due to the time zone difference. Prepare for a bit warmer weather when traveling from Chicago in July: high temperatures in Orlando hover around °C and lows are around °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

Side Trips

Daytona Beach, Kissimmee, Cherie Down Park, Stetson Mansion, Fishing Charters & Tours
Find places to stay Jul 21 — 31:
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Fishing Charters & Tours
Disney's Typhoon Lagoon Water Park ©
Disney's Typhoon Lagoon Water Park

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