10 days in New York City & Chicago Itinerary

10 days in New York City & Chicago Itinerary

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Route & dates

10 days in New York City & Chicago Itinerary

Start: New York City
1
New York City
— 5 nights
bus + Fly:  4​h 45​min
2
Chicago
— 4 nights
Fly + bus:  4​h 45​min
End: New York City

5
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.
Museum-lovers will get to explore The Metropolitan Museum of Art and American Museum of Natural History. Deepen your sense of the past at sights like 9/11 Memorial and Gateway National Recreation. There's still lots to do: take a stroll through Times Square, admire the striking features of Empire State Building, don't miss a visit to Fifth Avenue, and see the interesting displays at New York Public Library.

To find photos, traveler tips, ratings, and other tourist information, read our New York City online sightseeing planner .

Use the Route module to find travel options from your starting location to New York City. Expect a daytime high around 80°F in June, and nighttime lows around 65°F. Wrap up your sightseeing on the 9th (Sat) to allow time to travel to Chicago.

Things to do in New York City

Museums Neighborhoods Parks

Side Trip

Gateway National Recreation
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Appreciate the collections at The Art Institute of Chicago and The Field Museum. Deepen your sense of the past at sights like Millennium Park and Frank Lloyd Wright Home and Studio. Change things up with these side-trips from Chicago: Silver Beach County Park (in Saint Joseph) and Whihala Beach Co Park (in Whiting). Next up on the itinerary: take a stroll through The Magnificent Mile, engage your brain at Museum of Science and Industry, take in panoramic vistas at Skydeck Chicago - Willis Tower, and admire the landmark architecture of Rockefeller Memorial Chapel.

To see reviews, maps, and other tourist information, read our Chicago trip planner .

Do a combination of bus and flight from New York City to Chicago in 5 hours. Alternatively, you can fly; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Expect a daytime high around 81°F in June, and nighttime lows around 63°F. Wrap up your sightseeing on the 13th (Wed) to allow time to travel back home.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

Oak Park, Whihala Beach, Silver Beach County Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
Field Museum ©
Field Museum

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