20 days in New York City, Florida & Chicago Itinerary

20 days in New York City, Florida & Chicago Itinerary

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Route & dates

20 days in New York City, Florida & Chicago Itinerary

Start: Boracay
+2
ferry + foot + Fly:  27​h
1
New York City
— 7 nights
Fly:  5​h 45​min
2
Orlando
— 5 nights
Fly:  5​h
3
Chicago
— 4 nights
+2
Fly + foot + ferry:  27​h
End: Boracay

7
nights
New York City

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.
New York City is known for museums, nightlife, historic sites, parks, and shopping. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, pause for some photo ops at 9/11 Memorial, admire the striking features of Grand Central Terminal, and make a trip to Rockefeller Center.

To see other places to visit, photos, traveler tips, and more tourist information, go to the New York City trip maker app .

Boracay, Philippines to New York City is an approximately 27-hour combination of ferry, flight, and bus. You can also do a combination of ferry, bus, and flight. The time zone changes from Philippines Time to Eastern Standard Time, which is usually a -13 hour difference. Traveling from Boracay in June, expect New York City to be slightly colder, temps between 31°C and 21°C. Finish up your sightseeing early on the 26th (Tue) so you can travel to Orlando.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

5
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.
Pack the 27th (Wed) with family-friendly diversions at Walt Disney World Resort. Pack the 28th (Thu) with family-friendly diversions at Universal's Islands of Adventure. And it doesn't end there: make an unforgettable trip to Magic Kingdom Park, get in on the family fun at Epcot, laugh and play at Disney's Hollywood Studios, and take in a show at Happily Ever After Fireworks.

Plan a trip to Orlando easily and quickly by telling Inspirock to suggest an itinerary.

Do a combination of bus and flight from New York City to Orlando in 6 hours. Alternatively, you can do a combination of train and flight; or drive. In June, Orlando is a bit warmer than New York City - with highs of 38°C and lows of 26°C. Wrap up your sightseeing by early afternoon on the 1st (Sun) to allow time for travel to Chicago.

Things to do in Orlando

Theme Parks Outdoors Parks
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Walt Disney World Resort ©
Walt Disney World Resort

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, see the interesting displays at The Field Museum, get curious at Museum of Science and Industry, and appreciate the extensive heritage of Millennium Park.

For reviews, where to stay, ratings, and more tourist information, refer to the Chicago trip planner .

Getting from Orlando to Chicago by flight takes about 5 hours. Other options: do a combination of train and flight; or drive. You'll gain 1 hour traveling from Orlando to Chicago due to the time zone difference. Expect a bit cooler temperatures when traveling from Orlando in July; daily highs in Chicago reach 33°C and lows reach 22°C. Finish up your sightseeing early on the 5th (Thu) so you can travel back home.

Things to do in Chicago

Museums Childrens Museums Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field
Museum of Science and Industry ©
Museum of Science and Industry

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