31 days in New York City & Chicago Itinerary

31 days in New York City & Chicago Itinerary

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31 days in New York City & Chicago Itinerary

Chicago
Fly + bus:  4​h 45​min
New York City
— 2 nights
bus + Fly:  4​h 45​min
Chicago
— 28 nights
Chicago

2
days
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.
Central Park has been added to your itinerary. Kick off your visit on the 15th (Fri): make a trip to 9/11 Memorial and then don't miss a visit to Central Park. Get ready for a full day of sightseeing on the 16th (Sat): take in panoramic vistas at Empire State Building and then explore the world behind art at The Metropolitan Museum of Art.

To see where to stay, other places to visit, maps, and other tourist information, refer to the New York City itinerary maker.

Chicago to New York City is an approximately 5-hour combination of flight and bus. You can also drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Expect somewhat warmer evenings in New York City when traveling from Chicago in September, with lows around 22°C. Finish up your sightseeing early on the 17th (Sun) so you can travel to Chicago.

Things to do in New York City

Parks Museums Historic Sites
Accommodations
Get expert advice on where to stay in New York City.
Find places to stay »
Highlights from your plan
Central Park
The Metropolitan Museum of Art
Empire State Building

29
days
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Elawa Farm (in Lake Forest), Schaumburg (Schaumburg Boomers Stadium & FireZone) and Chicago Botanic Garden (in Glencoe). Plan for a day of cool, family-friendly fun on the 28th (Thu) at Six Flags Great America. Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to The Magnificent Mile, meet the residents at Lincoln Park Zoo, and get curious at Museum of Science and Industry, Chicago.

For more things to do, photos, traveler tips, and other tourist information, use the Chicago trip generator.

Traveling by combination of bus and flight from New York City to Chicago takes 5 hours. Alternatively, you can drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Traveling from New York City in September, Chicago is a bit cooler at night with lows of 18°C. Cap off your sightseeing on the 15th (Sun) early enough to travel back home.

Things to do in Chicago

Parks Outdoors Theme Parks

Side Trips

Oak Park, Schaumburg, South Bend, Saint Joseph, Aurora
Accommodations
Get expert advice on where to stay in Chicago.
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Highlights from your plan
Millennium Park
The Art Institute of Chicago
Wrigley Field

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