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, thenget to know the fascinating history of Chicago Riverwalk, thencontemplate the waterfront views at Chicago River, and finally get a new perspective on things with Boat Tours & Water Sports.

To see maps, photos, and other tourist information, read Chicago online trip itinerary maker.

Memphis to Chicago is an approximately 5.5-hour flight. You can also drive; or take a train. Expect a bit cooler temperatures when traveling from Memphis in July; daily highs in Chicago reach °F and lows reach °F. Finish your sightseeing early on the 21st (Tue) so you can travel to Philadelphia.

Things to do in Chicago

Historic Sites Museums Outdoors

Side Trips

Ernest Hemingway Birthplace, Baha'i House of Worship
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 Silverball Pinball Museum. You'll explore and learn at National Museum of American Jewish History and Battleship New Jersey. Change things up with these side-trips from Philadelphia: Belmar Beach (in Belmar), Ocean Grove Beach (in Ocean Grove) and Cape May (World War II Lookout Tower & Cape May City Beaches). And it doesn't end there: witness the site of a historic battle at Valley Forge National Historical Park, take an in-depth tour of National Constitution Center, explore the world behind art at Philadelphia's Magic Gardens, and contemplate in the serene atmosphere at Daylesford Abbey.

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 °F and lows of °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, Battleship New Jersey, Belmar Beach, Valley Forge National Historical Park, Silverball Pinball Museum
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 National Monument to the Forefathers. You'll explore the less-touristy side of things at Old North Church & Historic Site and USS Albacore Museum. Change things up with these side-trips from Boston: Strawbery Banke Museum (in Portsmouth), Long Sands Beach (in York Beach) and Plymouth (Burial Hill, The Jenney, &more). Next up on the itinerary: contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, wander the streets of Waterfront, stroll the grounds of Granary Burying Ground, and visit Back Bay.

To see ratings, traveler tips, more things to do, and more tourist information, you can read our Boston vacation planner.

You can fly from Philadelphia to Boston in 4 hours. Alternatively, you can drive; or take a train. Prepare for a bit cooler weather when traveling from Philadelphia in July: high temperatures in Boston hover around °F and lows are around °F. Wrap up your sightseeing on the 28th (Tue) early enough to travel back home.

Things to do in Boston

Historic Sites Parks Museums

Side Trips

Plymouth, Portsmouth, Long Sands Beach, Hampton Beach State Park
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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