31 days in New York City & Chicago Itinerary

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.

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Chicago to New York City is an approximately 5.5-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 31°C, while nighttime lows are 22°C. Finish your sightseeing early on the 17th (Sun) so you can travel to 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 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, pause for some serene contemplation at Basilica of the Sacred Heart, stroll around Millennium Park, and get curious at Museum of Science and Industry.

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Traveling by flight from New York City to Chicago takes 5.5 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 19°C. Finish your sightseeing early on the 15th (Sun) so you can travel back home.