12 days in Chicago & New York City Itinerary

12 days in Chicago & New York City Itinerary

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Route & dates

12 days in Chicago & New York City Itinerary

Start: Punta Cana, Dominican Republic
Fly:  8​h 15​min
1
Chicago
— 5 nights
Fly + Bus:  4​h 45​min
2
New York City
— 5 nights
Fly:  7​h 45​min
End: Punta Cana, Dominican Republic

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Family-friendly places like Silver Beach County Park and Shedd Aquarium will thrill your kids. Step off the beaten path and head to The Magnificent Mile and Carpenter Creek Cellars. Explore the numerous day-trip ideas around Chicago: St. Julian Winery-Union Pier (in Union Pier), Kernel's Gourmet Popcorn & More (in Geneva) and Prarie States Winery (in Genoa). And it doesn't end there: engage your brain at Museum of Science and Industry, see the interesting displays at The Field Museum, try your luck at Horseshoe Hammond, and explore and take pictures at Millennium Park.

To see maps, more things to do, ratings, and tourist information, go to the Chicago trip itinerary site .

Punta Cana, Dominican Republic to Chicago is an approximately 8.5-hour flight. You can also do a combination of shuttle and flight. The time zone difference when traveling from Punta Cana to Chicago is minus 2 hours. In December, Chicago is much colder than Punta Cana - with highs of 3°C and lows of -3°C. Finish your sightseeing early on the 21st (Fri) to allow enough time to travel to New York City.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Carpenter Creek Cellars, Prairie States Winery, Silver Beach County Park, Horseshoe Hammond, St. Julian Winery & Distillery
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry
Field Museum ©
Field Museum

5
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.
Appreciate the collections at Golden Fish Gallery and The Metropolitan Museum of Art. Step off the beaten path and head to Fifth Avenue and Bashakill Vineyards. You'll find plenty of places to visit near New York City: Paumanok Vineyards (in Aquebogue) and Ponquogue Beach (in Hampton Bays). There's much more to do: appreciate the history behind 9/11 Memorial, take in the pleasant sights at Times Square, make a trip to Central Park, and take a stroll through SoHo.

To see maps, where to stay, reviews, and tourist information, refer to the New York City tour planner .

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Traveling from Chicago in December, things will get somewhat warmer in New York City: highs are around 10°C and lows about 2°C. Finish your sightseeing early on the 26th (Wed) so you can travel back home.

Things to do in New York City

Parks Neighborhoods Museums

Side Trips

Paumanok Vineyards, Golden Fish Gallery, Bashakill Vineyards, Ponquogue Beach
Highlights from your plan
Greenwich Village ©
Greenwich Village
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial

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