22 days in New York City & Chicago Itinerary

22 days in New York City & Chicago Itinerary

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Route & dates

22 days in New York City & Chicago Itinerary

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

11
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.
Shop till you drop at Fifth Avenue and DM Weil Gallery. Get some cultural insight at Times Square and The Metropolitan Museum of Art. Change things up with a short trip to Angry Orchard in Walden (about 1h 35 min away). The adventure continues: take in the pleasant sights at Central Park, enjoy breathtaking views from Empire State Building, learn more about the world around you at American Museum of Natural History, and admire all the interesting features of The High Line.

For traveler tips, other places to visit, photos, and more tourist information, read our New York City trip itinerary maker .

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. Traveling from Auckland to New York City, you'll gain 17 hours due to the time zone difference. Traveling from Auckland in October, you will find days in New York City are a bit warmer (24°C), and nights are about the same (16°C). Cap off your sightseeing on the 3rd (Sun) early enough to travel to Chicago.

Things to do in New York City

Museums Neighborhoods Shopping

Side Trips

Angry Orchard, DM Weil Gallery, Norwood Museum
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Times Square ©
Times Square
9/11 Memorial ©
9/11 Memorial

9
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do some cultural sightseeing at The Art Institute of Chicago and Chicago Cultural Center. For shopping fun, head to The Magnificent Mile or Illinois Holocaust Museum & Education Center. Venture out of the city with trips to South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, & more), Prairie States Winery (in Genoa) and Whiskey Acres Distilling Co. (in DeKalb). There's lots more to do: engage your brain at Museum of Science and Industry, contemplate the long history of Ernest Hemingway Birthplace, wander the streets of Wicker Park, and get to know the resident critters at Lincoln Park Zoo.

To see traveler tips, other places to visit, maps, and tourist information, use the Chicago online trip builder .

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. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Plan for a bit cooler temperatures traveling from New York City in November, with highs in Chicago at 11°C and lows at 1°C. Wrap up your sightseeing on the 12th (Tue) to allow time to travel back home.

Things to do in Chicago

Museums Shopping Childrens Museums

Side Trips

South Bend, Oak Park, Skokie, Whiskey Acres Distilling Co., Prairie States Winery
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

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