15 days in Chicago, East Coast of USA & Bennington Itinerary

15 days in Chicago, East Coast of USA & Bennington Itinerary

Created using Inspirock United States trip planner

Make it your trip
Fly
1
Chicago
— 3 nights
Fly
2
Washington DC
— 2 nights
Train
3
New York City
— 5 nights
Fly
4
Boston
— 2 nights
Fly
5
Bennington
— 2 nights
Fly

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Chicago

— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 21st (Thu): don't miss a visit to Buckingham Fountain, get a new perspective on things with Boat Tours & Water Sports, then stroll through Millennium Park, and finally explore the world behind art at The Art Institute of Chicago. Keep things going the next day: learn more about the world around you at Field Museum, then get up close and personal with brilliant marine life at Shedd Aquarium, then admire the striking features of Chicago Board of Trade Building, and finally make a trip to Skydeck Chicago - Willis Tower.

To find reviews, more things to do, and tourist information, use the Chicago route planning site.

San Francisco to Chicago is an approximately 6-hour flight. You can also drive; or do a combination of subway and train. You'll lose 2 hours traveling from San Francisco to Chicago due to the time zone difference. Plan for slightly colder temperatures traveling from San Francisco in October, with highs in Chicago at 65°F and lows at 49°F. Cap off your sightseeing on the 23rd (Sat) early enough to catch the flight to Washington DC.

Things to do in Chicago

Museums · Parks · Childrens Museums · Outdoors

Washington DC

— 2 nights
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Washington DC is known for museums, historic sites, and nightlife. Your trip includes some of its best attractions: examine the collection at National Air and Space Museum, appreciate the history behind Washington Monument, get a sense of history and politics at White House, and get your bearings at Library of Congress.

To see maps, other places to visit, reviews, and other tourist information, read Washington DC trip site.

Traveling by flight from Chicago to Washington DC takes 3.5 hours. Alternatively, you can drive; or take a train. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. While traveling from Chicago, expect somewhat warmer days and about the same nights in Washington DC, ranging from highs of 71°F to lows of 54°F. Finish up your sightseeing early on the 25th (Mon) so you can catch the flight to New York City.

Things to do in Washington DC

Museums

New York City

— 5 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: take in the pleasant sights at Central Park, stroll around The High Line, admire the landmark architecture of Grand Central Terminal, and explore the galleries of The Metropolitan Museum of Art.

For where to stay, ratings, more things to do, and tourist information, go to the New York City vacation planner.

Traveling by flight from Washington DC to New York City takes 3 hours. Alternatively, you can take a train; or drive. In October in New York City, expect temperatures between 70°F during the day and 57°F at night. Finish up your sightseeing early on the 30th (Sat) so you can catch the flight to Boston.

Things to do in New York City

Parks · Museums · Neighborhoods · Historic Sites

Boston

— 2 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.
Start off your visit on the 30th (Sat): take an in-depth tour of John F. Kennedy Presidential Museum & Library and then appreciate the extensive heritage of Freedom Trail. On your second day here, buy something for everyone on your list at Faneuil Hall Marketplace, then walk around Boston Public Garden, then stroll around Boston Common, and finally visit North End.

To see more things to do, other places to visit, photos, and more tourist information, use the Boston travel route planner.

Getting from New York City to Boston by flight takes about 2.5 hours. Other options: drive; or take a train. Traveling from New York City in October, things will get slightly colder in Boston: highs are around 64°F and lows about 50°F. Finish your sightseeing early on the 1st (Mon) to allow enough time to fly to Bennington.

Things to do in Boston

Parks · Neighborhoods · Historic Sites · Museums

Bennington

— 2 nights
Bennington is a town in Bennington County, Vermont, in the United States. Bennington is known for shopping, museums, and historic sites. Your trip includes some of its best attractions: explore the world behind art at The Clark Art Institute, stop by Bringing You Vermont, take some stellar pictures from Bennington Battle Monument, and relax and rejuvenate at Green Mountain Oasis.

To see photos, maps, more things to do, and other tourist information, read Bennington road trip planner.

Traveling by flight from Boston to Bennington takes 3 hours. Alternatively, you can drive; or take a bus. Plan for little chillier nights when traveling from Boston in November since evenings lows in Bennington dip to 29°F. Wrap up your sightseeing on the 3rd (Wed) to allow time to fly back home.

Things to do in Bennington

Museums · Shopping · Historic Sites · Spas

Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Hiking Trails
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.