17 days in Boston & Chicago Itinerary

17 days in Boston & Chicago Itinerary

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Route & dates

17 days in Boston & Chicago Itinerary

Start: San Francisco
Fly:  7​h 15​min
1
Boston
— 10 nights
Fly:  4​h
2
Chicago
— 6 nights
Fly:  6​h
End: San Francisco

10
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.
Explore Boston's surroundings by going to Provincetown (Pilgrim Monument & Provincetown Museum & Race Point Beach), Marginal Way Walkway (in Ogunquit) and Salem (Salem Witch Museum & Peabody Essex Museum). The adventure continues: admire all the interesting features of Fenway Park, appreciate the extensive heritage of Freedom Trail, engage your brain at Sandwich Glass Museum, and stroll the grounds of Mount Auburn Cemetery.

To find photos, more things to do, reviews, and other tourist information, go to the Boston trip builder .

San Francisco to Boston is an approximately 7.5-hour combination of flight and bus. You can also do a combination of train, flight, and bus; or drive. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. In May in Boston, expect temperatures between 67°F during the day and 51°F at night. Wrap up your sightseeing on the 14th (Mon) to allow time to travel to Chicago.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Sandwich, Brookline, Provincetown, Salem, Marginal Way Walkway
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Freedom Trail ©
Freedom Trail
Boston Public Garden ©
Boston Public Garden

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, wander the streets of The Magnificent Mile, explore and take pictures at Wrigley Field, and admire nature's wide array of creatures at Shedd Aquarium.

For traveler tips, maps, where to stay, and more tourist information, use the Chicago day trip app .

Traveling by combination of bus and flight from Boston to Chicago takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Boston to Chicago. In May in Chicago, expect temperatures between 72°F during the day and 53°F at night. Wrap up your sightseeing on the 20th (Sun) early enough to travel back home.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Horseshoe Hammond
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

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