31 days in New York City & Chicago Itinerary

31 days in New York City & Chicago Itinerary

Created using Inspirock United States Trip Planner

Plan created by another user. Make it yours

Route & dates

1
New York City
— 2 nights
2
Chicago
— 28 nights

2
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.
You've now added Central Park to your itinerary. Kick off your visit on the 15th (Fri): examine the collection at 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 overwheling when you use's Insprock itinerary maker.

Chicago to New York City is an approximately 5-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 °C, while nighttime lows are °C. Finish your sightseeing early on the 17th (Sun) so you can travel to Chicago.

Things to do in New York City

Parks Museums Historic Sites
Find places to stay Sep 15 — 17:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

28
nights
Chicago

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 Schaumburg (Schaumburg Boomers Stadium & FireZone), Chicago Botanic Garden (in Glencoe) and Elawa Farm (in Lake Forest). 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, pause for some serene contemplation at Basilica of the Sacred Heart, 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 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. Plan for a bit cooler nights when traveling from New York City in September since evenings lows in Chicago dip to °C. Finish your sightseeing early on the 15th (Sun) so you can travel back home.

Things to do in Chicago

Parks Outdoors Theme Parks

Side Trips

Oak Park, Aurora, Oak Brook, Schaumburg, Saint Joseph
Find places to stay Sep 17 — Oct 15:
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field

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