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.

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.

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 Chicago Botanic Garden (in Glencoe), Schaumburg (Schaumburg Boomers Stadium & FireZone) and Elawa Farm (in Lake Forest). Plan for a day of cool, family-friendly fun on the 28th (Thu) at Six Flags Great America. There's still lots to do: explore the world behind art at The Art Institute of Chicago, admire the local landmark of Buckingham Fountain, meet the residents at Lincoln Park Zoo, and engage your brain at Museum of Science and Industry.

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

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to fly; or drive. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Traveling from New York City in September, plan for slightly colder nights in Chicago, with lows around 19°C. Wrap up your sightseeing on the 15th (Sun) to allow time to travel back home.