10 days in Chicago, Philadelphia & Boston Itinerary

10 days in Chicago, Philadelphia & Boston Itinerary

Created using Inspirock United States tour builder

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

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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.
On the 19th (Sun), look for gifts at Ernest Hemingway Birthplace and then ponder the design of Buckingham Fountain. Here are some ideas for day two: examine the collection at Money Museum at the Federal Reserve Bank, admire the masterpieces at The Art Institute of Chicago, then get to know the fascinating history of Chicago Riverwalk, then contemplate the waterfront views at Chicago River, and finally get a new perspective on things with Boat Tours & Water Sports.

For where to stay, reviews, traveler tips, and other tourist information, refer to the Chicago road trip planner.

Memphis to Chicago is an approximately 5-hour bus ride. You can also fly; or drive; or take a bus. Prepare for little chillier weather when traveling from Memphis in July: high temperatures in Chicago hover around 83°F and lows are around 67°F. Wrap up your sightseeing on the 21st (Tue) to allow time to fly to Philadelphia.

Things to do in Chicago

Historic Sites · Museums · Outdoors · Parks

Side Trips

Philadelphia

— 4 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.
Get some cultural insight at Cape May Lighthouse and Valley Forge National Historical Park. Your itinerary includes some good beach time at Cape May City Beaches and Ocean Grove Beach. Change things up with these side-trips from Philadelphia: Silverball Retro Arcade Asbury Park (in Asbury Park), World War II Lookout Tower (in Cape May) and Belmar Beach (in Belmar). The adventure continues: appreciate the extensive heritage of Independence Mall, explore the world behind art at Rodin Museum, get engrossed in the history at National Constitution Center, and contemplate in the serene atmosphere at Masonic Temple.

For reviews, other places to visit, maps, and more tourist information, refer to the Philadelphia trip maker.

Getting from Chicago to Philadelphia by flight takes about 3.5 hours. Other options: drive; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. July in Philadelphia sees daily highs of 88°F and lows of 72°F at night. Finish your sightseeing early on the 25th (Sat) so you can fly to Boston.

Things to do in Philadelphia

Historic Sites · Museums · Parks · Beaches

Side Trips

Boston

— 3 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.
Get outdoors at Hampton Beach State Park and Castle Island. You'll explore the less-touristy side of things at Old North Church & Historic Site and Strawbery Banke Museum. Change things up with these side-trips from Boston: USS Albacore Museum (in Portsmouth), Long Sands Beach (in York Beach) and Plymouth (Burial Hill, The Jenney, &more). Next up on the itinerary: take a stroll through Back Bay, visit Waterfront, and stroll the grounds of Granary Burying Ground.

To see other places to visit, where to stay, more things to do, and tourist information, read our Boston trip itinerary maker website.

You can fly from Philadelphia to Boston in 3.5 hours. Alternatively, you can drive; or take a train. Traveling from Philadelphia in July, things will get a bit cooler in Boston: highs are around 83°F and lows about 67°F. Cap off your sightseeing on the 28th (Tue) early enough to catch the flight back home.

Things to do in Boston

Historic Sites · Parks · Museums · Beaches

Side Trips