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

Windy City

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, then admire the striking features of Baha'i House of Worship, then brush up on your military savvy at Cantigny Park, and finally appreciate the extensive heritage of Riverwalk Lot.

To see where to stay, photos, and more tourist information, refer to the Chicago travel route planner.

Memphis to Chicago is an approximately 6-hour flight. You can also drive; or take a bus. Prepare for slightly colder weather when traveling from Memphis in July: high temperatures in Chicago hover around 83°F and lows are around 67°F. Cap off your sightseeing on the 21st (Tue) early enough to travel to Philadelphia.

Things to do in Chicago

Historic Sites · Museums · Outdoors · Adventure

Side Trips

2
nights
Philadelphia

The City of Brotherly Love

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, then get 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, then examine 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 88°F and lows of 72°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 · Shopping

Side Trips

5
nights
Boston

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.
Popular historic sites such as Old North Church & Historic Site and Louisa May Alcott's Orchard House are in your itinerary. Museum-lovers will get to explore International Tennis Hall of Fame and National Museum of American Illustration. You'll find plenty of places to visit near Boston: West Yarmouth (Seagull Beach & Whydah Pirate Museum), Newport (Audrain Automobile Museum & Marble House) and Kalmus Beach (in Hyannis). The adventure continues: witness the site of a historic battle at Minute Man National Historical Park, identify plant and animal life at Wildlife Areas, explore the world behind art at Harvard Art Museums, and wander the streets of Waterfront.

To see traveler tips, where to stay, ratings, and more tourist information, use the Boston day trip site.

Getting from Philadelphia to Boston by flight takes about 4 hours. Other options: drive; or take a train. Prepare for little chillier weather when traveling from Philadelphia in July: high temperatures in Boston hover around 83°F and lows are around 67°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 · Outdoors

Side Trips