20 days in Orlando, Chicago & New York City Itinerary

20 days in Orlando, Chicago & New York City Itinerary

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Route & dates

20 days in Orlando, Chicago & New York City Itinerary

Start: Hyderabad
Fly:  23​h 15​min
1
Orlando
— 2 nights
Fly:  19​h 15​min
2
Chicago
— 6 nights
Fly + Bus:  4​h 45​min
3
New York City
— 7 nights
Bus + Fly:  19​h 15​min
End: Hyderabad

2
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.
Go for a jaunt from Orlando to DeLand to see Stetson Mansion about 1 hour away. Pack the 22nd (Sat) with family-friendly diversions at Walt Disney World Resort. Have a day of magic on the 21st (Fri) at Disney's Animal Kingdom. There's more to do: laugh and play at Happily Ever After Fireworks and browse the different shops at The Mall at Millenia.

To find other places to visit, reviews, ratings, and other tourist information, read our Orlando online itinerary planner .

Hyderabad, India to Orlando is an approximately 23.5-hour flight. You can also do a combination of flight and bus. You'll gain 10 hours traveling from Hyderabad to Orlando due to the time zone difference. In September, daytime highs in Orlando are 37°C, while nighttime lows are 27°C. Finish up your sightseeing early on the 23rd (Sun) so you can go by car to Chicago.

Things to do in Orlando

Theme Parks Shopping Historic Sites

Side Trip

Stetson Mansion
Highlights from your plan
Happily Ever After Fireworks ©
Happily Ever After Fireworks
Stetson Mansion ©
Stetson Mansion
The Mall at Millenia ©
The Mall at Millenia

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Popular historic sites such as Millennium Park and Marquette Building are in your itinerary. Get some cultural insight at The Art Institute of Chicago and The Magnificent Mile. Explore Chicago's surroundings by going to Grand Mere State Park (in Stevensville), Bengtson's Pumpkin Farm (in Homer Glen) and Silver Beach County Park (in Saint Joseph). Next up on the itinerary: stroll through Little Red Schoolhouse, look for all kinds of wild species at Willowbrook Wildlife Center, explore and take pictures at Wrigley Field, and try your luck at Horseshoe Hammond.

Plan my trip to Chicago with suggested itineraries provided by Inspirock.

Traveling by car from Orlando to Chicago takes 19.5 hours. Alternatively, you can take a bus; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In September, Chicago is slightly colder than Orlando - with highs of 30°C and lows of 19°C. Finish your sightseeing early on the 30th (Sun) so you can travel to New York City.

Things to do in Chicago

Parks Outdoors Wildlife

Side Trips

Bengtson's Pumpkin Fest, Cowles Bog, Silver Beach County Park, Little Red Schoolhouse, Whihala Beach
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

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.
Get some cultural insight at Fifth Avenue and 9/11 Memorial. Take a break from the city and head to Narwhal Yacht Charters and Bronx Zoo. Change things up with a short trip to Cupsogue Beach County Park in Westhampton Beach (about 1h 40 min away). There's much more to do: explore the world behind art at The Metropolitan Museum of Art, get a new perspective on nature at American Museum of Natural History, take in the architecture and atmosphere at St. Patrick's Cathedral, and take in the pleasant sights at Times Square.

For photos, traveler tips, maps, and more tourist information, read our New York City route builder app .

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Other options are to fly; or drive. The time zone difference when traveling from Chicago to New York City is 1 hour. Traveling from Chicago in October, plan for somewhat warmer nights in New York City, with lows around 16°C. Finish your sightseeing early on the 8th (Mon) to allow enough time to travel back home.

Things to do in New York City

Museums Parks Outdoors

Side Trips

Bronx Zoo, Cupsogue Beach County Park
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Ellis Island ©
Ellis Island

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