18 days in New York City, Boston & Chicago Itinerary

18 days in New York City, Boston & Chicago Itinerary

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Route & dates

18 days in New York City, Boston & Chicago Itinerary

Start: Santiago
Fly:  14​h 30​min
1
New York City
— 6 nights
bus + Fly:  3​h
2
Boston
— 3 nights
Fly:  4​h
3
Chicago
— 6 nights
Fly:  16​h
End: Santiago

6
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.
Your list of things to see and do now includes Top of the Rock, Greenwich Village, The High Line, and other attractions. Satisfy your inner culture vulture at Fifth Avenue and New York Public Library. The adventure continues: go for a walk through Central Park and admire the masterpieces at The Museum of Modern Art (MoMA).

For other places to visit, where to stay, and tourist information, refer to the New York City road trip tool .

Santiago, Chile to New York City is an approximately 14.5-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. Due to the time zone difference, you'll gain 1 hour traveling from Santiago to New York City. In June, daytime highs in New York City are 31°C, while nighttime lows are 21°C. You will leave for Boston on the 7th (Fri).

Things to do in New York City

Parks Neighborhoods Shopping

Side Trips

Brooklyn, Yankee Stadium, The Mills at Jersey Gardens, Astoria Park, Borough Hall Staten Island
Highlights from your plan
Fifth Avenue ©
Fifth Avenue
The Museum of Modern Art (MoMA)
The Museum of Modern Art (MoMA)
New York Public Library ©
New York Public Library

3
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Your day-by-day itinerary now includes Back Bay, Newbury Street, Boston Public Garden, and other attractions you added. There's still lots to do: buy something for everyone on your list at Faneuil Hall Marketplace, get to know the fascinating history of Freedom Trail, and admire all the interesting features of Fenway Park.

To find traveler tips, maps, reviews, and other tourist information, read our Boston itinerary planner .

Traveling by combination of bus and flight from New York City to Boston takes 3 hours. Alternatively, you can fly; or drive. Traveling from New York City in June, you can expect nighttime temperatures to be slightly colder in Boston, with lows of 18°C. On the 10th (Mon), you're off toChicago.

Things to do in Boston

Neighborhoods Shopping Parks

Side Trip

Harvard University
Highlights from your plan
Newbury Street ©
Newbury Street
Isabella Stewart Gardner Museum ©
Isabella Stewart Gardner Museum
Freedom Trail ©
Freedom Trail

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've added Merchandise Mart, The 606, Chicago Cultural Center, and other attractions to your itinerary. Satisfy your inner culture vulture at The Art Institute of Chicago and Millennium Park. Next up on the itinerary: wander the streets of The Magnificent Mile, take a leisurely stroll along Navy Pier, and examine the collection at The Field Museum.

To see traveler tips, ratings, reviews, and other tourist information, read Chicago trip site .

You can fly from Boston to Chicago in 4 hours. Other options are to do a combination of bus and flight; or drive. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In June, daytime highs in Chicago are 32°C, while nighttime lows are 20°C. On the 16th (Sun), you're off tohome.

Things to do in Chicago

Parks Neighborhoods Museums

Side Trip

Brookfield Zoo
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Field Museum ©
The Field Museum

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