12 days in Chicago & Boston Itinerary

12 days in Chicago & Boston Itinerary

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Route & dates

12 days in Chicago & Boston Itinerary

Start: Rimini
Fly:  26​h
1
Chicago
— 2 nights
Fly:  4​h
2
Boston
— 7 nights
Fly:  18​h 45​min
End: Rimini

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
The Art Institute of Chicago and Chicago Cultural Center will appeal to museum buffs. Your cultural itinerary includes sights like The Magnificent Mile and Millennium Park. There's much more to do: admire nature's wide array of creatures at Lincoln Park Zoo, enjoy breathtaking views from Skydeck Chicago - Willis Tower, explore and take pictures at Wrigley Field, and examine the collection at The Field Museum.

To see more things to do, where to stay, maps, and tourist information, read our Chicago online journey planner .

Rimini, Italy to Chicago is an approximately 26-hour flight. The time zone changes from Central European Time to Central Standard Time, which is usually a -7 hour difference. In August, daytime highs in Chicago are 33°C, while nighttime lows are 22°C. Finish your sightseeing early on the 8th (Thu) to allow enough time to travel to Boston.

Things to do in Chicago

Museums Childrens Museums Shopping
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

7
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.
Museum-lovers will get to explore Museum of Fine Arts and Pilgrim Monument & Provincetown Museum. Head to Faneuil Hall Marketplace and Gourmet Boutiquefor plenty of shopping. Explore the numerous day-trip ideas around Boston: Cliff Walk (in Newport), Marginal Way Walkway (in Ogunquit) and Beavertail Lighthouse and Park (in Jamestown). Next up on the itinerary: kick back and relax at Race Point Beach, see majestic marine mammals with a dolphin and whale watching tour, explore the activities along Cape Cod Canal, and tour the pleasant surroundings at Herring Cove Beach.

To find maps, ratings, photos, and more tourist information, go to the Boston trip itinerary planner.

Traveling by combination of flight and bus from Chicago to Boston takes 4 hours. Alternatively, you can do a combination of flight, taxi, and bus; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In August in Boston, expect temperatures between 32°C during the day and 21°C at night. Wrap up your sightseeing on the 15th (Thu) early enough to travel back home.

Things to do in Boston

Outdoors Parks Historic Sites

Side Trips

Provincetown, Beavertail Lighthouse and Park, Brooklyn Boulders, Cape Cod Canal, Marginal Way Walkway
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

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