9 days in New York City & Chicago Itinerary

9 days in New York City & Chicago Itinerary

Created using Inspirock United States trip itinerary planner

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1
New York City
— 4 nights
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2
Chicago
— 3 nights
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4
nights
New York City

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
You'll discover tucked-away gems like Franklin D. Roosevelt Presidential Library and Museum and Chelsea Market. Vanderbilt Mansion National Historic Site and Home of Franklin D. Roosevelt will appeal to history buffs. When in New York City, make a side trip to see Woodbury Common Premium Outlets in Central Valley, approximately Central Valley away. There's still lots to do: take in the spiritual surroundings of The Met Cloisters, savor the flavors at Food & Drink, pause for some serene contemplation at St. Patrick's Cathedral, and get to know the fascinating history of Brooklyn Heights Promenade.

To see other places to visit, more things to do, ratings, and other tourist information, you can read our New York City trip itinerary maker website.

Auckland, New Zealand to New York City is an approximately 19.5-hour flight. The time zone changes from New Zealand Standard Time (NZST) to Eastern Standard Time (EST), which is usually a -17 hour difference. Traveling from Auckland in September, expect nights in New York City to be a bit warmer, around 22°C, while days are much warmer, around 31°C. Finish your sightseeing early on the 14th (Sat) so you can travel to Chicago.

Things to do in New York City

Historic Sites · Museums · Shopping · Tours

Side Trips

3
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 15th (Sun): contemplate the waterfront views at Lake Michigan, appreciate the extensive heritage of Chicago Riverwalk, and then trek along Lakefront Trail. On the 16th (Mon), you'll have a packed day of sightseeing: sample some tasty brews at a beer tour and tasting, get a taste of the local shopping with The Magnificent Mile, and then admire the striking features of Chicago Cultural Center.

To see ratings, more things to do, maps, and more tourist information, go to the Chicago sightseeing planner.

Traveling by flight from New York City to Chicago takes 5 hours. Alternatively, you can drive; or take a bus. You'll gain 1 hour traveling from New York City to Chicago due to the time zone difference. Plan for slightly colder nights when traveling from New York City in September since evenings lows in Chicago dip to 19°C. Finish your sightseeing early on the 17th (Tue) so you can travel back home.

Things to do in Chicago

Parks · Shopping · Breweries & Distilleries · Tours

Side Trip