27 days in New York City, Orlando & Chicago Itinerary

27 days in New York City, Orlando & Chicago Itinerary

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Route & dates

27 days in New York City, Orlando & Chicago Itinerary

Start: New York City
1
New York City
— 6 nights
Fly:  6​h
2
Orlando
— 12 nights
Fly:  5​h
3
Chicago
— 7 nights
Fly + Bus:  4​h 45​min
End: New York City

6
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.
Kids will appreciate attractions like Central Park and New York Public Library. And it doesn't end there: admire the masterpieces at The Metropolitan Museum of Art, admire the striking features of Rockefeller Center, don't miss a visit to Empire State Building, and tour the pleasant surroundings at The High Line.

For other places to visit, where to stay, more things to do, and other tourist information, read New York City trip planner.

If you are flying in from India, the closest major airports are La Guardia Airport, Newark Liberty International Airport, John F Kennedy International Airport and Stewart International Airport. In April, daily temperatures in New York City can reach 19°C, while at night they dip to 8°C. Wrap up your sightseeing by early afternoon on the 30th (Sun) to allow enough time to fly to Orlando.

Things to do in New York City

Museums Parks Historic Sites

Side Trip

Brooklyn Botanic Garden
Find places to stay Apr 23 — 30:
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Statue of Liberty National Monument ©

12
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.
You'll visit kid-friendly attractions like Discovery Cove and Universal's Islands of Adventure. Get out of town with these interesting Orlando side-trips: Tampa Bay Water Bike Company (in Tampa) and Celebration Bike Rental (in Celebration). Pack the 4th (Thu) with family-friendly diversions at Walt Disney World Resort. Plan for a day of cool, family-friendly fun on the 10th (Wed) at Wet 'n Wild Orlando. And it doesn't end there: find something for the whole family at SeaWorld Orlando, have fun at Paddleboard Orlando, try out the rides at Disney's Animal Kingdom, and cool off at Universal Orlando Resort.

To see ratings, other places to visit, maps, and other tourist information, you can read our Orlando online itinerary creator.

Traveling by flight from New York City to Orlando takes 7 hours. Alternatively, you can drive; or do a combination of bus and shuttle. Plan for a bit warmer temperatures traveling from New York City in May, with highs in Orlando at 36°C and lows at 24°C. Wrap up your sightseeing by early afternoon on the 12th (Fri) to allow time for the flight to Chicago.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trips

Winter Park, Celebration Bike Rental and Bicycle Tours, Tampa Bay Water Bike Company
Find places to stay Apr 30 — May 12:
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Walt Disney World Resort ©
Walt Disney World Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Family-friendly places like Lincoln Park Zoo and Museum of Science and Industry, Chicago will thrill your kids. Change things up with a short trip to FireZone in Schaumburg (about 44 minutes away). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at 360 CHICAGO, admire nature's wide array of creatures at Shedd Aquarium, and don't miss a visit to The Magnificent Mile.

To see ratings, maps, traveler tips, and more tourist information, use the Chicago holiday planner.

You can fly from Orlando to Chicago in 6.5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Orlando to Chicago. Plan for slightly colder temperatures traveling from Orlando in May, with highs in Chicago at 25°C and lows at 13°C.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

FireZone, Northwestern University
Find places to stay May 12 — 19:
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Lincoln Park Zoo ©
Lincoln Park Zoo
Shedd Aquarium ©
Shedd Aquarium

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