10 days in Chicago, Philadelphia & Boston Itinerary

10 days in Chicago, Philadelphia & Boston Itinerary

Created using Inspirock United States planner

Make it your trip
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1
Chicago
— 2 nights
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2
Philadelphia
— 2 nights
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3
Boston
— 5 nights
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Chicago

— 2 nights

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

Memphis to Chicago is an approximately 3.5-hour flight. You can also drive; or take a bus. Plan for a bit cooler temperatures traveling from Memphis in July, with highs in Chicago at 83°F and lows at 67°F. Cap off your sightseeing on the 21st (Tue) early enough to catch the flight to Philadelphia.

Things to do in Chicago

Historic Sites · Museums · Outdoors · Adventure

Side Trips

Philadelphia

— 2 nights

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
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, take an in-depth tour of Battleship New Jersey, then get engrossed in the history at Museum of the American Revolution, and finally view 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 3.5 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 fly to Boston.

Things to do in Philadelphia

Museums · Historic Sites · Neighborhoods · Shopping

Side Trips

Boston

— 5 nights

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 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: Newport (Audrain Automobile Museum & National Museum of American Illustration), West Yarmouth (Seagull Beach & Whydah Pirate Museum) and Kalmus Beach (in Hyannis). The adventure continues: enjoy the sand and surf at Mayflower Beach, visit Waterfront, explore the world behind art at Harvard Art Museums, and see majestic marine mammals with a dolphin and whale watching tour.

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 3.5 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 fly back home.

Things to do in Boston

Historic Sites · Museums · Parks · Outdoors

Side Trips