21 days in Chicago, Boston & New York City Itinerary

21 days in Chicago, Boston & New York City Itinerary

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Route & dates

21 days in Chicago, Boston & New York City Itinerary

Start: Jerusalem
bus + Fly:  17​h 45​min
1
Chicago
— 6 nights
Fly:  4​h
2
Boston
— 5 nights
Fly + bus:  3​h
3
New York City
— 8 nights
Fly:  15​h 45​min
End: Jerusalem

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visiting Montrose Point Bird Sanctuary and Lakefront Trail will get you outdoors. Next up on the itinerary: wander the streets of The Magnificent Mile, admire the masterpieces at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, and kick back and relax at Kathy Osterman Beach.

To see reviews, maps, ratings, and tourist information, go to the Chicago trip itinerary planning app .

Jerusalem, Israel to Chicago is an approximately 18-hour combination of bus and flight. You'll gain 8 hours traveling from Jerusalem to Chicago due to the time zone difference. Plan for little chillier temperatures traveling from Jerusalem in September, with highs in Chicago at 30°C and lows at 19°C. Finish up your sightseeing early on the 5th (Sat) so you can travel to Boston.

Things to do in Chicago

Parks Outdoors Museums
Find places to stay Sep 29 — Oct 5:
Highlights from your plan
Lakefront Trail ©
Lakefront Trail
The Magnificent Mile ©
The Magnificent Mile
Montrose Point Bird Sanctuary ©
Montrose Point Bird Sanctuary

5
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.
Head to Newbury Street and Faneuil Hall Marketplacefor some retail therapy. Take a break from the city and head to Charles River Esplanade and Boston Harbor Islands National Recreation Area. Next up on the itinerary: explore the world behind art at Museum of Fine Arts, explore the wealth of natural beauty at Boston African American National Historic Site, wander the streets of North End, and get to know the fascinating history of Freedom Trail.

To find maps, where to stay, and other tourist information, go to the Boston journey tool .

Traveling by flight from Chicago to Boston takes 4 hours. Alternatively, you can do a combination of flight and bus; or drive. Traveling from Chicago to Boston, you'll lose 1 hour due to the time zone difference. In October, daily temperatures in Boston can reach 20°C, while at night they dip to 11°C. Finish your sightseeing early on the 10th (Thu) so you can travel to New York City.

Things to do in Boston

Parks Nature Historic Sites

Side Trip

Boston Harbor Islands National Recreation Area
Find places to stay Oct 5 — 10:
Highlights from your plan
Charles River Esplanade ©
Charles River Esplanade
Newbury Street ©
Newbury Street
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace

8
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.
Visiting East River Waterfront Esplanade and West Side Community Garden will get you outdoors. Shop till you drop at Fifth Avenue and West Village. There's still lots to do: wander the streets of Times Square, pick up some new knowledge with The Golf Club at Chelsea Piers, enjoy breathtaking views from Empire State Building, and get some thrills on the water with a speed boat tour.

To see where to stay, maps, more things to do, and tourist information, you can read our New York City online tour itinerary planner .

You can do a combination of flight and bus from Boston to New York City in 3 hours. Other options are to fly; or drive. Expect a bit warmer temperatures when traveling from Boston in October; daily highs in New York City reach 24°C and lows reach 16°C. Wrap up your sightseeing on the 18th (Fri) early enough to travel back home.

Things to do in New York City

Parks Outdoors Trails
Find places to stay Oct 10 — 18:
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Fifth Avenue ©
Fifth Avenue

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