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.

Explore the numerous day-trip ideas around Chicago: 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. Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to Buckingham Fountain, meet the residents at Lincoln Park Zoo, 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 combination of bus and flight from New York City to Chicago takes 5 hours. Alternatively, you can fly; or drive. 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.