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.

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.

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), Chicago Botanic Garden (in Glencoe) and Schaumburg (Schaumburg Boomers Stadium & FireZone). There's much more to do: admire the masterpieces at The Art Institute of Chicago, take in the architecture and atmosphere at Basilica of the Sacred Heart, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and meet the residents at Shedd Aquarium.

For other places to visit, maps, traveler tips, and more tourist information, read Chicago trip planner.

Fly from New York City to Chicago in 4 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. 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.