10 days in Chicago, Philadelphia & Boston Itinerary

10 days in Chicago, Philadelphia & Boston Itinerary

Created using Inspirock United States tour builder

Plan created by another user. Make it yours

Route & dates

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

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 19th (Sun), contemplate the long history of 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 5.5-hour flight. You can also drive; or take a train. 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 travel to Philadelphia.

Things to do in Chicago

Historic Sites · Museums · Outdoors

Side Trips

Baha'i House of Worship, Ernest Hemingway Birthplace
Find places to stay Jul 19 — 21:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Baha'i House of Worship ©
Baha'i House of Worship
Richard H. Driehaus Museum ©
Richard H. Driehaus Museum

4
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Get a sense of the local culture at Cape May Lighthouse and Valley Forge National Historical Park. You'll explore and learn at National Museum of American Jewish History and National Constitution Center. Change things up with these side-trips from Philadelphia: Belmar Beach (in Belmar), Ocean Grove Beach (in Ocean Grove) and Silverball Pinball Museum (in Asbury Park). And it doesn't end there: get to know the fascinating history of Independence Mall, take some stellar pictures from World War II Lookout Tower, take in the architecture and atmosphere at Christ Church, and explore the world behind art at Rodin Museum.

To see where to stay, traveler tips, photos, and other tourist information, refer to the Philadelphia trip itinerary maker.

You can fly from Chicago to Philadelphia in 4.5 hours. Other options are to drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Philadelphia. July in Philadelphia sees daily highs of 88°F and lows of 72°F at night. Finish up your sightseeing early on the 25th (Sat) so you can travel to Boston.

Things to do in Philadelphia

Historic Sites · Museums · Parks

Side Trips

Cape May, Daylesford Abbey, Belmar Beach, Wildwood Beach, Valley Forge National Historical Park
Find places to stay Jul 21 — 25:
Highlights from your plan
Ocean Grove Beach ©
Ocean Grove Beach
Cape May Lighthouse ©
Cape May Lighthouse
Cape May City Beaches ©
Cape May City Beaches

3
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.
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 Long Sands Beach. Change things up with these side-trips from Boston: Portsmouth (USS Albacore Museum & Strawbery Banke Museum) and Plymouth (Burial Hill, The Jenney, &more). And it doesn't end there: wander the streets of Back Bay, stroll the grounds of Granary Burying Ground, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, and stop by Waterfront.

To find more things to do, reviews, where to stay, and tourist information, read Boston itinerary planner.

Fly from Philadelphia to Boston in 4 hours. Alternatively, you can drive; or take a train. Prepare for slightly colder weather when traveling from Philadelphia in July: high temperatures in Boston hover around 83°F and lows are around 67°F. Finish your sightseeing early on the 28th (Tue) so you can travel back home.

Things to do in Boston

Historic Sites · Parks · Museums

Side Trips

Plymouth, Portsmouth, Hampton Beach State Park, Long Sands Beach
Find places to stay Jul 25 — 28:
Highlights from your plan
Back Bay ©
Back Bay
Hampton Beach State Park ©
Hampton Beach State Park
Long Sands Beach ©
Long Sands Beach

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