15 days in Boston, New York City & Chicago Itinerary

15 days in Boston, New York City & Chicago Itinerary

Created using Inspirock United States trip planner

This plan was created by another user.  Make it your plan

Route & dates

15 days in Boston, New York City & Chicago Itinerary

Start: Cork
bus + Fly:  10​h 30​min
1
Boston
— 5 nights
Fly + bus:  3​h
2
New York City
— 5 nights
bus + Fly:  4​h 45​min
3
Chicago
— 3 nights
Fly + bus:  14​h 15​min
End: Cork

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.
Get some historical perspective at Beavertail Lighthouse and Park and Orchard House. Your itinerary includes some good beach time at Long Point and Nantasket Beach. Get out of town with these interesting Boston side-trips: National Monument to the Forefathers (in Plymouth), Cape Cod Canal (in Buzzards Bay) and Provincetown (Race Point Beach & Herring Cove Beach). And it doesn't end there: relax in the rural setting at Wright's Dairy Farm and Bakery, immerse yourself in nature at Walden Pond State Reservation, appreciate the history behind New England Holocaust Memorial, and take a stroll through Newbury Street.

To see where to stay, photos, maps, and more tourist information, go to the Boston route tool .

Cork, Ireland to Boston is an approximately 10.5-hour combination of bus, flight, and train. You can also do a combination of train, bus, and flight; or do a combination of bus and flight. The time zone difference when traveling from Cork to Boston is minus 5 hours. While traveling from Cork, expect a bit warmer days and about the same nights in Boston, ranging from highs of 22°C to lows of 11°C. Finish your sightseeing early on the 17th (Fri) to allow enough time to travel to New York City.

Things to do in Boston

Parks Beaches Outdoors

Side Trips

Provincetown, Concord, Wright's Dairy Farm and Bakery, Nantasket Beach, Cape Cod Canal
Highlights from your plan
Long Point ©
Long Point
Museum of Fine Arts ©
Museum of Fine Arts
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House

5
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.
Popular historic sites such as 9/11 Memorial and Ellis Island are in your itinerary. Satisfy your inner culture vulture at Fifth Avenue and The Metropolitan Museum of Art. There's lots more to do: choose your vessel at Tribeca Sailing, get a new perspective on nature at American Museum of Natural History, wander the streets of Times Square, and go all around town with Narwhal Yacht Charters.

To see reviews, other places to visit, traveler tips, and other tourist information, refer to the New York City trip planner .

Traveling by combination of bus and flight from Boston to New York City takes 3 hours. Alternatively, you can do a combination of bus and flight; or drive. May in New York City sees daily highs of 24°C and lows of 15°C at night. Finish up your sightseeing early on the 22nd (Wed) so you can travel to Chicago.

Things to do in New York City

Museums Outdoors Tours
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Satisfy your inner culture vulture at The Art Institute of Chicago and Museum of Science and Industry. Museum-lovers will appreciate Illinois Holocaust Museum & Education Center and Chicago Cultural Center. And it doesn't end there: meet the residents at Lincoln Park Zoo, contemplate in the serene atmosphere at Fourth Presbyterian Church, admire the local landmark of Buckingham Fountain, and don't miss a visit to The Magnificent Mile.

To find where to stay, other places to visit, maps, and other tourist information, read Chicago trip app .

Traveling by combination of bus and flight from New York City to Chicago takes 5 hours. Alternatively, you can fly; or drive. The time zone difference when traveling from New York City to Chicago is minus 1 hour. In May, daytime highs in Chicago are 25°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 25th (Sat) to allow time to travel back home.

Things to do in Chicago

Museums Shopping Childrens Museums

Side Trip

Illinois Holocaust Museum & Education Center
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum
Museum of Science and Industry ©
Museum of Science and Industry

Similar Plans

17 days in United States BY A USER FROM INDIA December, kids, culture, romantic, historic sites, shopping, wildlife, slow & easy, popular sights PREFERENCES: December, kids, culture, romantic, historic sites, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 18 days in United States BY A USER FROM INDIA December, kids, romantic, beaches, historic sites, shopping, wildlife, popular sights PREFERENCES: December, kids, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 17 days in United States BY A USER FROM UNITED ARAB EMIRATES July, teens, kids, popular & hidden gems PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 16 days in United States BY A USER FROM UNITED KINGDOM July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 19 days in New York City BY A USER FROM THAILAND November, slow & easy, popular & hidden gems PREFERENCES: November ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 16 days in United States BY A USER FROM SAUDI ARABIA June, teens, kids, popular sights PREFERENCES: June, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 17 days in Boston, Martha's Vineyard & New York City BY A USER FROM CANADA August, kids, popular sights PREFERENCES: August, kids ATTRACTION STYLE: Popular sights PACE: Medium 18 days in United States BY A USER FROM AUSTRALIA December, teens, kids, popular sights PREFERENCES: December, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 17 days in New York City BY A USER FROM ROMANIA February, outdoors, romantic, beaches, hidden gems PREFERENCES: February, outdoors, romantic, beaches ATTRACTION STYLE: Hidden gems PACE: Medium 16 days in New York City & California BY A USER FROM UNITED KINGDOM March, popular & hidden gems PREFERENCES: March ATTRACTION STYLE: Popular & hidden gems PACE: Medium 19 days in Los Angeles, San Francisco & New York City BY A USER FROM AUSTRALIA July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium
View more plans