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

S M T W T F S
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

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 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 local highlights with Walking tours, 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

Side Trips

Philadelphia, Brooklyn, 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: Allen Park (in Ottawa), LaSalle Rotary Park (in LaSalle) and Starved Rock State Park (in Utica). 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 22°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, Allen Park, LaSalle Rotary Park, Starved Rock State 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 Disney's Typhoon Lagoon Water Park. You'll find plenty of places to visit near Orlando: Daytona Beach (Daytona International Speedway, Beach at Daytona Beach, &more), Stetson Mansion (in DeLand) and Cherie Down Park (in Cape Canaveral). Pack the 27th (Tue) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: discover the magic at Disney’s Blizzard Beach Water Park, make a trip to Cinderella Castle, see the interesting displays at Ponce de Leon Inlet Lighthouse & Museum, and enjoy some diversion at Machine Gun America.

To see where to stay, reviews, ratings, and more tourist information, use the Orlando road trip tool.

Traveling by flight from Chicago to Orlando takes 5.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Chicago to Orlando is 1 hour. Prepare for a bit 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

Side Trips

Daytona Beach, Kissimmee, Ponce de Leon Inlet Lighthouse & Museum, 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

Similar plans

32 days in United States BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 32 days in Newark & Orlando BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife Attraction style: Popular sights Pace: Medium 35 days in New York City & San Francisco BY A USER FROM IRELAND May, culture, outdoors, relaxing, historic sites, wildlife, slow & easy, hidden gems Preferences: May, culture, outdoors, relaxing, historic sites, wildlife Attraction style: Hidden gems Pace: Slow & easy 60 days in New York City & Cape Town BY A USER FROM PORTUGAL June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 32 days in Chicago BY A USER FROM UNITED STATES January, culture, outdoors, museums, shopping, wildlife, slow & easy, popular & hidden gems Preferences: January, culture, outdoors, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Slow & easy 30 days in United States BY A USER FROM UNITED KINGDOM June, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular sights Preferences: June, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife Attraction style: Popular sights Pace: Medium 58 days in West Coast, Calgary & New York City BY A USER FROM ISRAEL July, teens, kids, culture, outdoors, beaches, museums, wildlife, popular sights Preferences: July, teens, kids, culture, outdoors, beaches, museums, wildlife Attraction style: Popular sights Pace: Medium 60 days in New York City, West Coast & Calgary BY A USER FROM ISRAEL July, teens, kids, culture, outdoors, beaches, historic sites, museums, wildlife, popular & hidden gems Preferences: July, teens, kids, culture, outdoors, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 60 days in Asia, Europe & United States BY A USER FROM PAKISTAN November, culture, outdoors, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems Preferences: November, culture, outdoors, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 37 days in United States BY A USER FROM PAKISTAN June, culture, outdoors, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, culture, outdoors, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 38 days in United States BY A USER FROM UNITED KINGDOM March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 9 days in Chicago BY A USER FROM UNITED STATES August, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: August, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium
See more plans