22 days in Boston & Chicago Itinerary

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.

Museum-lovers will appreciate Museum of Fine Arts and Sandwich Glass Museum. Your itinerary includes some good beach time at Cape Cod National Seashore and Corn Hill Beach. Get out of town with these interesting Boston side-trips: Marginal Way Walkway (in Ogunquit), Drakes Island Beach (in Wells) and Fisherman's Walk (in York Harbor). And it doesn't end there: examine the collection at Heritage Museums & Gardens, get up close to creatures of the deep with Hyannis Whale Watcher Cruises, take an in-depth tour of John F. Kennedy Presidential Museum & Library, and kick back and relax at Nauset Beach.

For photos, other places to visit, reviews, and more tourist information, you can read our Boston online route planner.

Berlin, Germany to Boston is an approximately 12.5-hour flight. The time zone difference moving from Central European Standard Time (CET) to Eastern Standard Time (EST) is minus 6 hours. In June in Boston, expect temperatures between 28°C during the day and 18°C at night. Finish up your sightseeing early on the 27th (Tue) so you can catch the flight to Chicago.

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Let the collections at The Art Institute of Chicago and Chicago History Museum capture your imagination. Escape the urban bustle at Boat Tours & Water Sports and Kathy Osterman Beach. There's much more to do: stroll around Millennium Park, admire the local landmark of Buckingham Fountain, take a stroll through The Magnificent Mile, and admire the landmark architecture of Skydeck Chicago - Willis Tower.

To see other places to visit, maps, more things to do, and tourist information, use the Chicago trip itinerary planning app.

Fly from Boston to Chicago in 4 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In June, plan for daily highs up to 32°C, and evening lows to 20°C. Wrap up your sightseeing on the 5th (Wed) to allow time to fly back home.