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
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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 The Art Institute of Chicago will appeal to museum buffs. Satisfy your inner culture vulture at The Magnificent Mile and Field Museum. Get out of town with these interesting Chicago side-trips: Louis Joliet Mall (in Joliet), SaltTreeYoga (in Ottawa) and Westclox Museum (in Peru). The adventure continues: take in the exciting artwork at Chicago Cultural Center, stop by Chudnow Museum of Yesteryear, admire the striking features of Frank Lloyd Wright's Unity Temple, and see what you can catch with Big River Fly Fishing.

To see photos, traveler tips, other places to visit, and tourist information, you can read our Chicago trip itinerary planning site.

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. Finish your sightseeing early on the 10th (Sat) to allow enough 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 Fifth Avenue. Do your shopping at DM Weil Gallery and Kimmel Center for the Performing Arts. Get out of town with these interesting New York City side-trips: Hudson Beach Glass (in Beacon), Magazzino Italian Art (in Cold Spring) and Philadelphia (Boathouse Row, Rittenhouse Square, &more). And it doesn't end there: explore the world behind art at The Metropolitan Museum of Art, tour the pleasant surroundings at Central Park, take an in-depth tour of Ellis Island, and examine the collection at New York Public Library.

For maps, photos, reviews, and tourist information, you can read our New York City trip maker.

Getting from Chicago to New York City by flight takes about 4 hours. Other options: drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. 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