31 days in New York City & Chicago Itinerary

31 days in New York City & Chicago Itinerary

Created using Inspirock United States Trip Planner
Make it your trip
Fly
1
New York City
— 2 nights
Fly
2
Chicago
— 28 nights

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New York City — 2 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
You've now added Central Park 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. On the 16th (Sat), you'll have a packed day of sightseeing: admire the landmark architecture of Empire State Building and then admire the masterpieces at The Metropolitan Museum of Art.

Planning New York City trip won't be overwhelming when you use Inspirock's itinerary maker.

Chicago to New York City is an approximately 4-hour flight. You can also drive; or take a bus. The time zone difference when traveling from Chicago to New York City is 1 hour. In September, daytime highs in New York City are 31°C, while nighttime lows are 22°C. Finish your sightseeing early on the 17th (Sun) so you can fly to Chicago.
Parks · Museums · Historic Sites
Find places to stay Sep 15 — 17:

Chicago — 28 nights

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 Schaumburg (Schaumburg Boomers Stadium & FireZone), Elawa Farm (in Lake Forest) and Chicago Botanic Garden (in Glencoe). Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, admire the striking features of Frank Lloyd Wright Home and Studio, stroll around Millennium Park, and get curious at Museum of Science and Industry.

To find out how to plan a trip to Chicago, use our trip itinerary maker.

Traveling by flight from New York City to Chicago takes 4 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. Plan for a bit cooler nights when traveling from New York City in September since evenings lows in Chicago dip to 19°C. Finish your sightseeing early on the 15th (Sun) so you can travel back home.
Parks · Outdoors · Theme Parks · Museums
Side Trips
Find places to stay Sep 17 — Oct 15: