9 days in New York City & Chicago Itinerary

9 days in New York City & Chicago Itinerary

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Route & dates

9 days in New York City & Chicago Itinerary

Start: Auckland
Fly:  22​h 30​min
1
New York City
— 4 nights
bus + Fly:  4​h 45​min
2
Chicago
— 3 nights
Fly:  20​h 15​min
End: Auckland

4
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Discover out-of-the-way places like Woodbury Common Premium Outlets and The Met Cloisters. Deepen your sense of the past at sights like Franklin D. Roosevelt Presidential Library and Museum and Brooklyn Heights Promenade. Explore the numerous day-trip ideas around New York City: Hyde Park (Home of Franklin D. Roosevelt & Vanderbilt Mansion National Historic Site). There's lots more to do: hunt for treasures at Chelsea Market, indulge in some culinary diversions at a local gastronomic tour, pause for some serene contemplation at St. Patrick's Cathedral, and shop like a local with SoHo.

To find more things to do, where to stay, photos, and more tourist information, read New York City journey builder .

Auckland, New Zealand to New York City is an approximately 22.5-hour combination of flight and bus. You can also fly; or do a combination of flight and train. Due to the time zone difference, you'll gain 17 hours traveling from Auckland to New York City. Expect much warmer weather when traveling from Auckland in September: highs in New York City hover around 31°C, while lows dip to 22°C. Finish up your sightseeing early on the 14th (Sat) so you can travel to Chicago.

Things to do in New York City

Historic Sites Museums Shopping

Side Trips

Hyde Park, Brooklyn Heights Promenade, Woodbury Common Premium Outlets
Highlights from your plan

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 15th (Sun), contemplate the waterfront views at Lake Michigan, get to know the fascinating history of Chicago Riverwalk, and then stroll through Lakefront Trail. On your second day here, sample some tasty brews at a beer tour and tasting, then wander the streets of The Magnificent Mile, and then admire the landmark architecture of Chicago Cultural Center.

For where to stay, ratings, maps, and more tourist information, you can read our Chicago journey planner.

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. Traveling from New York City in September, plan for a bit cooler nights in Chicago, with lows around 19°C. Wrap up your sightseeing on the 17th (Tue) to allow time to travel back home.

Things to do in Chicago

Parks Shopping Tours

Side Trip

Lake Michigan
Highlights from your plan
Lake Michigan ©
Lake Michigan
Chicago Riverwalk ©
Chicago Riverwalk
The Magnificent Mile ©
The Magnificent Mile

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