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: Sao Paulo
Fly + bus:  13​h 30​min
1
New York City
— 6 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
— 3 nights
bus + Fly:  13​h 30​min
End: Sao Paulo

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.
Get some cultural insight at 9/11 Memorial and St. Patrick's Cathedral. Step out of the city life by going to Upper Delaware River and Jacobsburg State Park. Venture out of the city with trips to Blue Ridge Estate Winery (in Saylorsburg), Swartswood State Park (in Swartswood) and Grey Towers National Historic Site (in Milford). Next up on the itinerary: go for a walk through Central Park, tour the water at your own pace with Hudson River Expeditions, delve into the lush surroundings at Worthington State Forest, and do a tasting at Brook hollow winery.

To find other places to visit, maps, and other tourist information, use the New York City trip tool .

Sao Paulo, Brazil to New York City is an approximately 13.5-hour combination of flight and bus. You can also do a combination of bus and flight. The time zone difference moving from Brasilia Time to Eastern Standard Time is minus 2 hours. Prepare for a bit cooler weather when traveling from Sao Paulo in April: high temperatures in New York City hover around 19°C and lows are around 9°C. You will have some time to spend on the 3rd (Thu) before leaving for Boston.

Things to do in New York City

Parks Nature Historic Sites

Side Trips

Columbia, Swartswood State Park, Jacobsburg State Park, Grey Towers National Historic Site, Blue Ridge Estate Winery
Highlights from your plan
9/11 Memorial ©
9/11 Memorial
New York Public Library ©
New York Public Library
St. Patrick's Cathedral ©
St. Patrick's Cathedral

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.
Kick off your visit on the 3rd (Thu): wander the streets of Waterfront. Keep things going the next day: get to know the fascinating history of Freedom Trail, shop like a local with Newbury Street, and then wander the streets of Beacon Hill.

To see reviews, maps, other places to visit, and other tourist information, refer to the Boston online route planner .

Traveling by combination of flight and bus from New York City to Boston takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from New York City in May, plan for little chillier nights in Boston, with lows around 11°C. Wrap up your sightseeing on the 5th (Sat) early enough to travel to Chicago.

Things to do in Boston

Historic Sites Neighborhoods Parks

Side Trip

Frederick Law Olmsted National Historic Site
Highlights from your plan
Beacon Hill ©
Beacon Hill
Waterfront ©
Waterfront

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Starved Rock State Park and Geneva Lake Shore Path. Do some cultural sightseeing at The Art Institute of Chicago and Millennium Park. Change things up with these side-trips from Chicago: August Hill Winery & Illinois Sparkling Co. Tasting Room (in Utica), Silver Beach County Park (in Saint Joseph) and Grand Mere State Park (in Stevensville). It doesn't end there: wander the streets of The Magnificent Mile and make a trip to Marquette Building.

For more things to do, where to stay, reviews, and other tourist information, go to the Chicago trip itinerary planning tool .

Do a combination of bus and flight from Boston to Chicago in 4 hours. Alternatively, you can do a combination of bus and flight; or drive. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In May, daytime highs in Chicago are 25°C, while nighttime lows are 13°C. Finish your sightseeing early on the 9th (Wed) so you can travel back home.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Utica, Grand Mere State Park, Silver Beach County Park, Geneva Lake Shore Path
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile

3
nights
New York City

New York City ©
Step off the beaten path and head to Pocono Environmental Education Center and Beardsley's Cider Mill & Orchard. Visiting Hudson Highlands State Park and The Celery Farm will get you outdoors. You'll find plenty of places to visit near New York City: Putnam Memorial State Park (in Redding) and Stokes State Forest (in Branchville). Enjoy New York City some more: get engrossed in the history at Ellis Island.

To find maps, photos, and tourist information, read New York City online trip itinerary builder .

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. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Cap off your sightseeing on the 13th (Sun) early enough to travel back home.

Things to do in New York City

Parks Nature Outdoors

Side Trips

Beardsley's Cider Mill & Orchard, Stokes State Forest, Pocono Environmental Education Center, Hudson Highlands State Park, The Celery Farm
Highlights from your plan
Pocono Environmental Education Center ©
Ellis Island ©
Ellis Island
Stokes State Forest ©
Stokes State Forest

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