10 days in Chicago, Philadelphia & Boston Itinerary

10 days in Chicago, Philadelphia & Boston Itinerary

Created using Inspirock United States planner

Plan created by another user. Make it yours

Route & dates

1
Chicago
— 2 nights
2
Philadelphia
— 2 nights
3
Boston
— 5 nights

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 19th (Sun): ponder the design of Buckingham Fountain and then get to know the fascinating history of Chicago Riverwalk. Here are some ideas for day two: explore the landscape on two wheels at Lakefront Trail, thenadmire the striking features of Baha'i House of Worship, thenbrush up on your military savvy at Cantigny Park, and finally appreciate the extensive heritage of Riverwalk Lot.

To find traveler tips, reviews, and tourist information, refer to the Chicago road trip planner.

Memphis to Chicago is an approximately 5.5-hour flight. You can also drive; or take a train. Plan for a bit cooler temperatures traveling from Memphis in July, with highs in Chicago at °F and lows at °F. Cap off your sightseeing on the 21st (Tue) early enough to travel to Philadelphia.

Things to do in Chicago

Historic Sites Museums Outdoors

Side Trips

Riverwalk Lot, Cantigny Park, Baha'i House of Worship
Highlights from your plan
Chicago Riverwalk ©
Chicago Riverwalk
Cantigny Park ©
Cantigny Park
Baha'i House of Worship ©
Baha'i House of Worship

2
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Kick off your visit on the 22nd (Wed): take an in-depth tour of Winterthur Museum, Garden & Library, admire the masterpieces at Brandywine River Museum of Art, contemplate the long history of Battleship New Jersey, thenget engrossed in the history at Museum of the American Revolution, and finally admire the masterpieces at Philadelphia's Magic Gardens. On the next day, contemplate in the serene atmosphere at Cathedral Basilica of Saints Peter and Paul, explore the world behind art at Rodin Museum, appreciate the extensive heritage of Independence Mall, deepen your understanding at National Museum of American Jewish History, thenexamine the collection at National Constitution Center, and finally pause for some serene contemplation at Christ Church.

For traveler tips, reviews, maps, and more tourist information, you can read our Philadelphia driving holiday planner.

Getting from Chicago to Philadelphia by flight takes about 4.5 hours. Other options: drive; or take a bus. Traveling from Chicago to Philadelphia, you'll lose 1 hour due to the time zone difference. July in Philadelphia sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 23rd (Thu) so you can travel to Boston.

Things to do in Philadelphia

Museums Historic Sites Neighborhoods

Side Trips

Brandywine River Museum of Art, Battleship New Jersey, Winterthur Museum, Garden & Library
Highlights from your plan
Winterthur Museum, Garden & Library ©
Winterthur Museum, Garden & Library
Brandywine River Museum of Art ©
Brandywine River Museum of Art
National Museum of American Jewish History ©

5
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.
Popular historic sites such as Old North Church & Historic Site and Marble House are in your itinerary. Museum-lovers will get to explore International Tennis Hall of Fame and Louisa May Alcott's Orchard House. You'll find plenty of places to visit near Boston: West Yarmouth (Seagull Beach & Whydah Pirate Museum), Kalmus Beach (in Hyannis) and Newport (Audrain Automobile Museum & National Museum of American Illustration). Next up on the itinerary: get engrossed in the history at Pilgrim Hall Museum, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, tour the pleasant surroundings at Castle Island, and see majestic marine mammals with a dolphin and whale watching tour.

To see ratings and tourist information, refer to the Boston tour planner.

You can fly from Philadelphia to Boston in 4 hours. Alternatively, you can drive; or take a train. In July, Boston is a bit cooler than Philadelphia - with highs of °F and lows of °F. Wrap up your sightseeing on the 28th (Tue) to allow time to travel back home.

Things to do in Boston

Historic Sites Museums Parks

Side Trips

Plymouth, Newport, Concord, West Yarmouth, Harvard Art Museums
Highlights from your plan
International Tennis Hall of Fame ©
International Tennis Hall of Fame
Minute Man National Historical Park ©
Minute Man National Historical Park
National Museum of American Illustration ©
National Museum of American Illustration

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