8 days in Chicago, Boston & New York City Itinerary

8 days in Chicago, Boston & New York City Itinerary

Created using Inspirock United States trip itinerary planner
Make it your trip
— 2 nights
— 2 nights
New York City
— 3 nights


Chicago — 2 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 22nd (Wed), admire the masterpieces at The Art Institute of Chicago, make a trip to Buckingham Fountain, engage your brain at Museum of Science and Industry, then contemplate the long history of Frank Lloyd Wright's Robie House, then try your luck at Horseshoe Hammond, and finally take a leisurely stroll along Navy Pier. Here are some ideas for day two: visit The Magnificent Mile, get curious at Field Museum, meet the residents at Shedd Aquarium, then learn about wildlife with up-close encounters at Lincoln Park Zoo, then take in panoramic vistas at 360 Chicago Observation Deck, and finally make a trip to Millennium Park.

To see photos, traveler tips, maps, and more tourist information, refer to the Chicago day trip planning site.

Use the Route module to see travel options from your home to Chicago. In December, daily temperatures in Chicago can reach 38°F, while at night they dip to 26°F. Finish up your sightseeing early on the 24th (Fri) so you can catch the flight to Boston.
Museums · Parks · Childrens Museums · Zoos & Aquariums
Side Trips

Boston — 2 nights

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 24th (Fri): explore the different monuments and memorials at Granary Burying Ground, walk around Boston Common, get curious at Museum of Science, admire the masterpieces at Museum of Fine Arts, then admire the natural beauty at Isabella Stewart Gardner Museum, and finally get a new perspective on nature at The Harvard Museum of Natural History. On the next day, appreciate the history behind New England Holocaust Memorial, take an in-depth tour of John F. Kennedy Presidential Museum & Library, admire the landmark architecture of Trinity Church, walk around Boston Public Garden, then make a trip to Faneuil Hall Marketplace, and finally get up close and personal with brilliant marine life at New England Aquarium.

Before you visit Boston, use our trip planner to discover what you can do and see there.

Getting from Chicago to Boston by flight takes about 4 hours. Other options: drive; or take a bus. Traveling from Chicago to Boston, you'll lose 1 hour due to the time zone difference. In December in Boston, expect temperatures between 43°F during the day and 31°F at night. Wrap up your sightseeing on the 26th (Sun) early enough to fly to New York City.
Museums · Historic Sites · Parks · Childrens Museums
Side Trip

New York City — 3 nights

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 sightseeing, museums, and nightlife. Your trip includes some of its best attractions: go for a walk through Central Park, take a stroll through Times Square, admire the striking features of Empire State Building, and contemplate the long history of 9/11 Memorial.

To find photos, other places to visit, where to stay, and tourist information, refer to the New York City road trip planning tool.

Fly from Boston to New York City in 3.5 hours. Alternatively, you can fly; or drive; or take a train. In December, plan for daily highs up to 48°F, and evening lows to 36°F.
Museums · Parks · Historic Sites · Tours