19 days in New York City, Boston & Chicago Itinerary

19 days in New York City, Boston & Chicago Itinerary

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Route & dates

19 days in New York City, Boston & Chicago Itinerary

Start: Buenos Aires
Fly:  14​h 45​min
1
New York City
— 7 nights
Bus + Fly:  3​h 15​min
2
Boston
— 2 nights
Fly:  4​h
3
Chicago
— 4 nights
Fly + Bus:  4​h 45​min
4
New York City
— 4 nights
Fly:  14​h 45​min
End: Buenos Aires

7
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.
Get some cultural insight at Fifth Avenue and New York Public Library. Get some historical perspective at St. Patrick's Cathedral and Grey Towers National Historic Site. Explore the numerous day-trip ideas around New York City: Jacobsburg State Park (in Nazareth), Pocono Environmental Education Center (in Dingmans Ferry) and Easton Farmers' Market (in Easton). Next up on the itinerary: step off the mainland to explore Fire Island National Seashore, take a peaceful walk through Worthington State Forest, experience rural life at Ort Farms, and explore the activities along Upper Delaware River.

For other places to visit, where to stay, reviews, and tourist information, read New York City trip maker tool .

Buenos Aires, Argentina to New York City is an approximately 15-hour flight. You can also do a combination of flight and train. Traveling from Buenos Aires to New York City, you'll gain 2 hours due to the time zone difference. Expect a bit cooler temperatures when traveling from Buenos Aires in April; daily highs in New York City reach 19°C and lows reach 9°C. Finish up your sightseeing early on the 3rd (Thu) so you can travel to Boston.

Things to do in New York City

Parks Nature Outdoors

Side Trips

Easton Farmers Market, Jacobsburg State Park, Swartswood State Park, Ort Farms, Fire Island National Seashore
Highlights from your plan
New York Public Library ©
New York Public Library
St. Patrick's Cathedral ©
St. Patrick's Cathedral
Fifth Avenue ©
Fifth Avenue

2
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.
Get some cultural insight at Museum of Fine Arts and Newbury Street. Discover out-of-the-way places like Faneuil Hall Marketplace and Beacon Hill. Venture out of the city with trips to Hampton Beach State Park (in Hampton) and Strawbery Banke Museum (in Portsmouth). The adventure continues: browse the eclectic array of goods at Quincy Market, get to know the fascinating history of Freedom Trail, and stroll through Isabella Stewart Gardner Museum.

To find reviews, maps, photos, and more tourist information, you can read our Boston trip itinerary planning app .

You can do a combination of flight and bus from New York City to Boston in 3.5 hours. Alternatively, you can drive; or take a bus. In May, daytime highs in Boston are 22°C, while nighttime lows are 12°C. Wrap up your sightseeing on the 5th (Sat) to allow time to travel to Chicago.

Things to do in Boston

Museums Parks Neighborhoods

Side Trips

Hampton Beach State Park, Strawbery Banke Museum
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Hampton Beach State Park ©
Hampton Beach State Park
Strawbery Banke Museum ©
Strawbery Banke Museum

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Millennium Park and Chicago Riverwalk. Escape the urban bustle at Grand Mere State Park and Silver Beach County Park. There's still lots to do: take a stroll through The Magnificent Mile, take in panoramic vistas at Skydeck Chicago - Willis Tower, admire the striking features of Chicago Cultural Center, and examine the collection at The Field Museum.

For ratings, where to stay, maps, and other tourist information, use the Chicago trip planner .

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. You'll gain 1 hour traveling from Boston to Chicago due to the time zone difference. In May, daily temperatures in Chicago can reach 26°C, while at night they dip to 13°C. You'll have a few hours on the 9th (Wed) to wrap things up before traveling to New York City.

Things to do in Chicago

Museums Parks Outdoors

Side Trips

Grand Mere State Park, Silver Beach County Park
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

4
nights
New York City

New York City ©
For shopping fun, head to Callie's Candy Kitchen or Callie's Pretzel Factory. Do some cultural sightseeing at Frick Collection and Grey Towers National Historic Site. Venture out of the city with trips to Bushkill Falls (in Bushkill), Upper Delaware River (in Narrowsburg) and House of Candles (in Henryville). Explore New York City further: browse the fresh offerings at Easton Farmers' Market and stop by Amazing Olive.

To find traveler tips, photos, ratings, and other tourist information, read New York City road trip planner .

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can do a combination of flight and train; or drive. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Finish your sightseeing early on the 13th (Sun) so you can travel back home.

Things to do in New York City

Nature Parks Shopping

Side Trips

Mountainhome, Easton Farmers Market, Amazing Olive, Grey Towers National Historic Site, House Of Candles
Highlights from your plan
Frick Collection ©
Frick Collection
Bushkill Falls ©
Bushkill Falls
Grey Towers National Historic Site ©
Grey Towers National Historic Site

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