7 days in Chicago, New York City & Orlando Itinerary

7 days in Chicago, New York City & Orlando Itinerary

Created using Inspirock United States trip itinerary builder

Plan created by another user. Make it yours
1
Chicago
— 1 night
2
New York City
— 3 nights
3
Orlando
— 1 night

S M T W T F S
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1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 17th (Sat): get up close and personal with brilliant marine life at Shedd Aquarium, then get curious at Field Museum, and then ponder the design of Buckingham Fountain. Keep things going the next day: make a trip to Skydeck Chicago - Willis Tower, contemplate in the serene atmosphere at Fourth Presbyterian Church, walk around Milton Lee Olive Park, then stroll around Millennium Park, and finally explore the world behind art at The Art Institute of Chicago.

To find ratings, traveler tips, and tourist information, read Chicago travel planner.

Miami to Chicago is an approximately 6-hour flight. You can also drive; or do a combination of bus and subway. Traveling from Miami to Chicago, you'll gain 1 hour due to the time zone difference. Traveling from Miami in October, things will get much colder in Chicago: highs are around 65°F and lows about 49°F. Finish up your sightseeing early on the 18th (Sun) so you can travel to New York City.

Things to do in Chicago

Museums · Parks · Childrens Museums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum
Shedd Aquarium ©
Shedd Aquarium

3
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, and shopping. Your plan includes some of its best attractions: go for a walk through Central Park, don't miss a visit to Statue of Liberty National Monument, browse the exhibits of 9/11 Memorial, and walk around The High Line.

To see ratings, other places to visit, traveler tips, and more tourist information, read our New York City online itinerary planner.

You can fly from Chicago to New York City in 5 hours. Alternatively, you can drive; or take a bus. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. Traveling from Chicago in October, New York City is somewhat warmer at night with lows of 57°F. Finish your sightseeing early on the 21st (Wed) to allow enough time to travel to Orlando.

Things to do in New York City

Parks · Museums · 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

1
night
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.
On the 22nd (Thu), find something for the whole family at Universal Orlando Resort. Keep things going the next day: get in on the family fun at Universal's Islands of Adventure.

To see traveler tips, more things to do, reviews, and other tourist information, use the Orlando driving holiday planning tool.

You can fly from New York City to Orlando in 6.5 hours. Alternatively, you can drive; or take a bus. Traveling from New York City in October, expect Orlando to be a bit warmer, temps between 85°F and 69°F. Wrap up your sightseeing on the 23rd (Fri) early enough to travel back home.

Things to do in Orlando

Theme Parks
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Universal Orlando Resort ©
Universal Orlando Resort

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