13 days in Chicago & New York City Itinerary

13 days in Chicago & New York City Itinerary

Created using Inspirock United States vacation planner
Make it your trip
1
Chicago
— 2 nights
Fly
2
New York City
— 10 nights

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Chicago — 2 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 21st (Wed): engage your brain at Museum of Science and Industry, then examine the collection at Oriental Institute Museum, then let the kids burn off some steam at Maggie Daley Park, and finally admire the landmark architecture of Chicago Cultural Center. Get ready for a full day of sightseeing on the next day: get a taste of the local shopping with Lincoln Park, then buy something for everyone on your list at Water Tower Place, and then admire the masterpieces at The Art Institute of Chicago.

To see where to stay, reviews, maps, and more tourist information, use the Chicago trip maker.

If you are flying in from Mexico, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In December, plan for daily highs up to 3°C, and evening lows to -3°C. Cap off your sightseeing on the 23rd (Fri) early enough to catch the flight to New York City.
Museums · Shopping · Parks · Childrens Museums

New York City — 10 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Step off the beaten path and head to The Museum of Modern Art (MoMA) and Franklin D. Roosevelt Presidential Library and Museum. Your cultural itinerary includes sights like The Metropolitan Museum of Art and Fifth Avenue. You'll find plenty of places to visit near New York City: Wright's Farm and Fruit Stand (in Gardiner), Woodbury Common Premium Outlets (in Central Valley) and Home of Franklin D. Roosevelt (in Hyde Park). There's much more to do: see the interesting displays at Ground Zero Museum Workshop, appreciate the extensive heritage of Brooklyn Heights Promenade, hit the best photo ops around with an inspiring photography tour, and take a stroll through SoHo.

To find more things to do, where to stay, ratings, and more tourist information, read our New York City trip itinerary planner.

You can fly from Chicago to New York City in 4 hours. Other options are to drive; or take a bus. The time zone difference when traveling from Chicago to New York City is 1 hour. Expect a bit warmer temperatures when traveling from Chicago in December; daily highs in New York City reach 10°C and lows reach 2°C.
Museums · Shopping · Neighborhoods · Tours
Side Trips