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 15​min
1
New York City
— 6 nights
Bus + Fly:  3​h 15​min
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.
Do your shopping at Fifth Avenue and Golden Fish Gallery. Museum-lovers will get to explore 9/11 Memorial and Alex Ferrone Gallery. Get out of town with these interesting New York City side-trips: Patchogue (The Amazing Olive & Fire Island National Seashore), Ponquogue Beach (in Hampton Bays) and The Amazing Olive (in Port Jefferson). There's lots more to do: revel in the low prices at Woodbury Common Premium Outlets, look for gifts at Li-Lac Chocolates, hunt for treasures at Chelsea Market, and enjoy the sand and surf at Compo Beach.

To find ratings, more things to do, and other tourist information, read New York City trip itinerary maker .

Santiago, Chile to New York City is an approximately 14.5-hour flight. You can also do a combination of flight and bus. You'll gain 1 hour traveling from Santiago to New York City due to the time zone difference. In June, daytime highs in New York City are 31°C, while nighttime lows are 21°C. Wrap up your sightseeing on the 7th (Fri) early enough to travel to Boston.

Things to do in New York City

Parks Outdoors Beaches

Side Trips

Patchogue, Ponquogue Beach, Ocean Grove Beach, Golden Fish Gallery, House Of Candles
Find places to stay Jun 1 — 7:
Highlights from your plan
Woodbury Common Premium Outlets ©
Woodbury Common Premium Outlets
9/11 Memorial ©
9/11 Memorial
Fifth Avenue ©
Fifth Avenue

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.
Kick off your visit on the 8th (Sat): admire the masterpieces at Museum of Fine Arts, take a stroll through Newbury Street, and then contemplate the long history of Harvard University. Keep things going the next day: explore the galleries of The House of the Seven Gables, hunt for treasures at Quincy Market, and then get to know the fascinating history of Freedom Trail.

Discover how to plan a Boston trip in just a few steps with Inspirock's itinerary builder.

Do a combination of flight and bus from New York City to Boston in 3.5 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from New York City in June, Boston is little chillier at night with lows of 18°C. Finish your sightseeing early on the 10th (Mon) so you can travel to Chicago.

Things to do in Boston

Historic Sites Museums Shopping

Side Trips

Harvard University, The House of the Seven Gables
Find places to stay Jun 7 — 10:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
The House of the Seven Gables ©
The House of the Seven Gables
Harvard University ©
Harvard University

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
John Deere Historic Site and Millennium Park will appeal to history buffs. Step off the beaten path and head to The Magnificent Mile and Grand Mere State Park. Change things up with these side-trips from Chicago: Basilica of the Sacred Heart (in South Bend), Saint Joseph (The Olive Cart & Silver Beach County Park) and Weber House and Garden (in Streator). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, stop by Stateline Blueberries, explore and take pictures at Wrigley Field, and stroll the grounds of Abraham Lincoln National Cemetery.

To find ratings, where to stay, reviews, and more tourist information, read our Chicago tour website .

You can do a combination of bus and flight from Boston to Chicago in 4 hours. Other options are to do a combination of train and flight; or drive. You'll gain 1 hour traveling from Boston to Chicago due to the time zone difference. In June, plan for daily highs up to 32°C, and evening lows to 20°C. Finish your sightseeing early on the 16th (Sun) so you can travel back home.

Things to do in Chicago

Parks Museums Outdoors

Side Trips

Saint Joseph, Grand Mere State Park, The Little Popcorn Store, Basilica of the Sacred Heart, Weber House and Garden
Find places to stay Jun 10 — 16:
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

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