19 days in Boston, Chicago & New York City Itinerary

19 days in Boston, Chicago & New York City Itinerary

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19 days in Boston, Chicago & New York City Itinerary

New York City
Fly + bus:  3​h 15​min
Boston
— 2 nights
bus + Fly:  4​h
Chicago
— 2 nights
Fly + bus:  4​h 45​min
New York City
— 14 nights
New York City

2
days
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 10th (Sun): appreciate the extensive heritage of Freedom Trail, admire all the interesting features of Fenway Park, and then admire the natural beauty at Boston Public Garden. Here are some ideas for day two: admire the masterpieces at Museum of Fine Arts, then make a trip to Boston Public Library, then get to know the fascinating history of Louisburg Square, and finally tour the pleasant surroundings at Boston Common.

To see maps, reviews, traveler tips, and tourist information, go to the Boston road trip website

New York City to Boston is an approximately 3.5-hour combination of flight and bus. You can also drive; or take a bus. Traveling from New York City in June, things will get little chillier in Boston: highs are around 28°C and lows about 17°C. Wrap up your sightseeing on the 12th (Tue) to allow time to travel to Chicago.

Things to do in Boston

Parks Museums Historic Sites
Highlights from your plan
Boston Public Garden ©
Boston Public Garden
Fenway Park ©
Fenway Park
Museum of Fine Arts
Museum of Fine Arts

2
days
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 12th (Tue): take in panoramic vistas at Skydeck Chicago - Willis Tower, explore the world behind art at The Art Institute of Chicago, and then explore and take pictures at Wrigley Field. Get ready for a full day of sightseeing on the 13th (Wed): make a trip to Cloud Gate, get to know the fascinating history of Millennium Park, then engage your brain at Museum of Science and Industry, Chicago, and finally meet the residents at Shedd Aquarium.

For traveler tips, maps, where to stay, and other tourist information, you can read our Chicago holiday app

Traveling by combination of bus and flight from Boston to Chicago takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from Boston to Chicago, you'll gain 1 hour due to the time zone difference. Traveling from Boston in June, expect nights in Chicago to be about the same, around 20°C, while days are somewhat warmer, around 32°C. Cap off your sightseeing on the 14th (Thu) early enough to travel to New York City.

Things to do in Chicago

Museums Childrens Museums Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field
Museum of Science and Industry, Chicago ©

15
days
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.
Change things up with a short trip to Bronx Zoo in Bronx (about 42 minutes away). The adventure continues: take in the pleasant sights at Central Park, explore the world behind art at The Metropolitan Museum of Art, admire the landmark architecture of Grand central terminal, and make a trip to Empire State Building.

To find more things to do, photos, other places to visit, and other tourist information, read our New York City trip planning website

Getting from Chicago to New York City by combination of flight and bus takes about 5 hours. Other options: do a combination of flight and train; or drive. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. In June, daytime highs in New York City are 31°C, while nighttime lows are 21°C. Cap off your sightseeing on the 28th (Thu) early enough to travel back home.

Things to do in New York City

Museums Parks Tours

Side Trips

Brooklyn, Bronx Zoo
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Central Park ©
Central Park
Empire State Building ©
Empire State Building

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