31 days in Chicago & New York City Itinerary

31 days in Chicago & New York City Itinerary

Created using Inspirock United States trip itinerary maker

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Chicago
— 10 nights
Fly
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New York City
— 19 nights
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Chicago

— 10 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Illinois Holocaust Museum & Education Center and Chicago Cultural Center will appeal to museum buffs. Satisfy your inner culture vulture at The Magnificent Mile and Chudnow Museum of Yesteryear. Get out of town with these interesting Chicago side-trips: Westclox Museum (in Peru), Louis Joliet Mall (in Joliet) and SaltTreeYoga (in Ottawa). There's much more to do: admire the masterpieces at The Art Institute of Chicago, observe the fascinating underwater world at Shedd Aquarium, get curious at Museum of Science and Industry, and admire the landmark architecture of Frank Lloyd Wright's Unity Temple.

To see photos, maps, more things to do, and more tourist information, you can read our Chicago trip planning tool.

Johannesburg, South Africa to Chicago is an approximately 22.5-hour flight. The time zone difference moving from South Africa Standard Time (SAST) to Central Standard Time (CST) is minus 8 hours. In March, Chicago is much colder than Johannesburg - with highs of 8°C and lows of -1°C. Wrap up your sightseeing on the 10th (Sat) to allow time to fly to New York City.

Things to do in Chicago

Museums · Wildlife · Parks · Shopping

Side Trips

New York City

— 19 nights

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.
Get some cultural insight at Times Square and 9/11 Memorial. Do your shopping at Fifth Avenue and Kimmel Center for the Performing Arts. Get out of town with these interesting New York City side-trips: Magazzino Italian Art (in Cold Spring), Hudson Beach Glass (in Beacon) and Philadelphia (Boathouse Row, Rittenhouse Square, &more). Next up on the itinerary: explore the world behind art at The Metropolitan Museum of Art, stroll through Central Park, examine the collection at New York Public Library, and don't miss a visit to Empire State Building.

To see photos, other places to visit, where to stay, and tourist information, you can read our New York City trip itinerary site.

Traveling by flight from Chicago to New York City takes 4 hours. Alternatively, you can drive; or take a bus. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. In April, daily temperatures in New York City can reach 19°C, while at night they dip to 8°C. Wrap up your sightseeing on the 29th (Thu) early enough to fly back home.

Things to do in New York City

Museums · Shopping · Neighborhoods · Parks

Side Trips