31 days in New York City, Boston & Chicago Itinerary

31 days in New York City, Boston & Chicago Itinerary

Created using Inspirock United States attractions planner

Make it your trip
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New York City
— 11 nights
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2
Boston
— 10 nights
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3
Chicago
— 7 nights
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New York City

— 11 nights

Big Apple

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, and shopping. Your trip includes some of its best attractions: enjoy breathtaking views from Empire State Building, admire the landmark architecture of Rockefeller Center, appreciate the history behind Statue of Liberty National Monument, and don't miss a visit to Grand Central Terminal.

To find more things to do, ratings, reviews, and other tourist information, read our New York City trip itinerary builder site.

Kuala Lumpur, Malaysia to New York City is an approximately 23.5-hour flight. Traveling from Kuala Lumpur to New York City, you'll gain 13 hours due to the time zone difference. Traveling from Kuala Lumpur in December, things will get colder in New York City: highs are around 10°C and lows about 2°C. Finish your sightseeing early on the 12th (Sun) to allow enough time to fly to Boston.

Things to do in New York City

Museums · Parks · Historic Sites · Neighborhoods

Side Trip

Boston

— 10 nights

Beantown

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.
Venture out of the city with trips to Lizzie Borden House (in Fall River), Ravenswood Park (in Gloucester) and New Hampshire Brews Cruise (in Portsmouth). There's lots more to do: explore the world behind art at Museum of Fine Arts, wander the streets of Charles Street, take an in-depth tour of Plimoth Patuxet, and admire the striking features of Trinity Church.

For more things to do, where to stay, maps, and tourist information, you can read our Boston attractions planner.

You can fly from New York City to Boston in 2.5 hours. Alternatively, you can drive; or take a train. Plan for a bit cooler temperatures traveling from New York City in December, with highs in Boston at 7°C and lows at 0°C. Wrap up your sightseeing on the 22nd (Wed) early enough to fly to Chicago.

Things to do in Boston

Museums · Historic Sites · Parks · Tours

Side Trips

Chicago

— 7 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, get curious at Museum of Science and Industry, stroll around Millennium Park, and learn more about the world around you at Field Museum.

For more things to do, maps, photos, and more tourist information, read Chicago online trip maker.

Getting from Boston to Chicago by flight takes about 4 hours. Other options: drive; or take a bus. You'll gain 1 hour traveling from Boston to Chicago due to the time zone difference. In December, Chicago is slightly colder than Boston - with highs of 3°C and lows of -3°C. Wrap up your sightseeing on the 29th (Wed) to allow time to fly back home.

Things to do in Chicago

Museums · Historic Sites · Childrens Museums · Parks

Side Trip