21 days in New England, Chicago & New York City Itinerary

21 days in New England, Chicago & New York City Itinerary

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Route & dates

21 days in New England, Chicago & New York City Itinerary

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

4
nights
Provincetown

Provincetown ©
A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Explore the numerous day-trip ideas around Provincetown: Chatham Marconi Maritime Center (in North Chatham) and Salt Pond Visitor Center (in Eastham). And it doesn't end there: kick back and relax at Cape Cod National Seashore, examine the collection at Provincetown Art Association and Museum, stroll through Marconi Beach, and take in the waterfront at MacMillan Wharf.

To see where to stay, traveler tips, and more tourist information, refer to the Provincetown trip maker .

Jerusalem, Israel to Provincetown is an approximately 15.5-hour combination of bus and flight. You can also do a combination of bus and flight. Traveling from Jerusalem to Provincetown, you'll gain 7 hours due to the time zone difference. In September, Provincetown is a bit cooler than Jerusalem - with highs of 25°C and lows of 16°C. Finish your sightseeing early on the 3rd (Thu) so you can drive to Sandwich.

Things to do in Provincetown

Parks Outdoors Beaches

Side Trips

Cape Cod, Marconi Beach, Salt Pond Visitor Center, Chatham Marconi Maritime Center, Truro Vineyards of Cape Cod
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©

3
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Get out of town with these interesting Sandwich side-trips: Edward Gorey House (in Yarmouth Port), Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge) and Falmouth (Highfield Hall & Gardens & Cornelia Carey Sanctuary (The Knob)). The adventure continues: see the interesting displays at Heritage Museums & Gardens, take an in-depth tour of Sandwich Glass Museum, appreciate the history behind Plymouth Rock, and make a trip to Old King's Hwy.

To find photos, where to stay, ratings, and more tourist information, refer to the Sandwich trip itinerary planner.

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. October in Sandwich sees daily highs of 20°C and lows of 9°C at night. Wrap up your sightseeing on the 6th (Sun) to allow time to take a bus to Boston.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

Falmouth, Chatham, Cape Cod Canal, Plymouth Rock, Edward Gorey House
Highlights from your plan
Monomoy National Wildlife Refuge ©
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

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.
Get out of town with these interesting Boston side-trips: Peabody Essex Museum (in Salem) and Louisa May Alcott's Orchard House (in Concord). And it doesn't end there: explore the world behind art at Museum of Fine Arts, contemplate in the serene atmosphere at Trinity Church, stroll the grounds of Mount Auburn Cemetery, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

To see photos, maps, ratings, and tourist information, go to the Boston travel route builder site .

Take a bus from Sandwich to Boston in an hour. Alternatively, you can drive. In October in Boston, expect temperatures between 20°C during the day and 11°C at night. Finish up your sightseeing early on the 9th (Wed) so you can travel to Chicago.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Cambridge, Peabody Essex Museum, Louisa May Alcott's Orchard House
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Mount Auburn Cemetery ©
Mount Auburn Cemetery

4
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with a short trip to Whiskey Acres Distilling Co. in DeKalb (about 1h 20 min away). There's much more to do: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to Buckingham Fountain, take in the local highlights with Walking tours, and examine the collection at The Field Museum.

To see ratings, traveler tips, more things to do, and more tourist information, go to the Chicago online tour planner .

Traveling by 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 October, daytime highs in Chicago are 21°C, while nighttime lows are 11°C. Wrap up your sightseeing on the 13th (Sun) to allow time to travel to New York City.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Whiskey Acres Distilling Co.
Highlights from your plan
Walking tours
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: go for a walk through Central Park, admire the landmark architecture of Rockefeller Center, don't miss a visit to Grand Central Terminal, and take in panoramic vistas at Top of the Rock.

Make your New York City itinerary with Inspirock to find out what to see and where to go.

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Plan for a bit warmer nights when traveling from Chicago in October since evenings lows in New York City dip to 16°C. Finish your sightseeing early on the 19th (Sat) so you can travel back home.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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