31 days in Chicago & New York City Itinerary

31 days in Chicago & New York City Itinerary

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Route & dates

31 days in Chicago & New York City Itinerary

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

15
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Venture out of the city with trips to Rockford (Anderson Japanese Gardens & Severson Dells Nature Center), Wheaton (Cantigny Park & First Division Museum at Cantigny) and Block Museum of Art (in Evanston). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, admire the landmark architecture of Skydeck Chicago - Willis Tower, take in panoramic vistas at 360 Chicago Observation Deck, and examine the collection at The Field Museum.

For where to stay, more things to do, maps, and tourist information, read our Chicago trip planner .

New York City to Chicago is an approximately 5-hour combination of bus and flight. You can also fly; or drive. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. In October, Chicago is slightly colder than New York City - with highs of 65°F and lows of 49°F. Wrap up your sightseeing on the 16th (Wed) to allow time to travel to New York City.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

South Bend, Oak Park, Milwaukee, Evanston, Wheaton
Highlights from your plan
Walking tours
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

15
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.
Change things up with these side-trips from New York City: Nutley Public Library (in Nutley), Overpeck County Park (in Leonia) and Philadelphia (Rodin Museum & Liberty Bell Center). There's still lots to do: walk around Central Park, don't miss a visit to Rockefeller Center, enjoy breathtaking views from Empire State Building, and pause for some photo ops at Statue of Liberty National Monument.

To see maps, reviews, more things to do, and tourist information, read New York City road trip planner.

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. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Traveling from Chicago in October, expect a bit warmer with lows of 57°F in New York City. Cap off your sightseeing on the 31st (Thu) early enough to travel back home.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Philadelphia, Overpeck County Park, Nutley Public Library, Brooklyn Botanic Garden
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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