5 days in Pennsylvania Itinerary

5 days in Pennsylvania Itinerary

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Route & dates

5 days in Pennsylvania Itinerary

Start: Chicago
Fly:  3​h 45​min
1
Pittsburgh
— Few hours
Fly + taxi:  3​h 45​min
2
Gettysburg
— 1 night
Drive:  1​h 15​min
3
Hershey
— 1 night
Drive:  1​h 45​min
4
Philadelphia
— 2 nights
Fly:  4​h
End: Chicago

few
hours
Pittsburgh

Pittsburgh ©
Known primarily for its steel-related heritage and 446 bridges, Pittsburgh sits at the confluence of the Monongahela and Allegheny Rivers, which meet to form the Ohio River.
Start off your visit on the 13th (Tue): admire all the interesting features of PNC Park and then snap pictures at Roberto Clemente Bridge (Sixth Street Bridge).

For reviews, more things to do, maps, and tourist information, refer to the Pittsburgh trip itinerary planning site .

Chicago to Pittsburgh is an approximately 4-hour flight. You can also drive; or take a train. You'll lose 1 hour traveling from Chicago to Pittsburgh due to the time zone difference. In August in Pittsburgh, expect temperatures between 80°F during the day and 63°F at night. Wrap up your sightseeing on the 13th (Tue) early enough to travel to Gettysburg.
Highlights from your plan
PNC Park ©
PNC Park

1
night
Gettysburg

Gettysburg ©
Located near the memorial park marking the site of one of the largest Civil War battles, the town of Gettysburg sits in a landscape of rolling green hills with views of the Blue Ridge Mountains in the distance.
Kick off your visit on the 14th (Wed): have some family-friendly fun at Victorian Photography Studio, explore and take pictures at Gettysburg National Military Park, then get engrossed in the history at Gettysburg National Military Park Museum & Visitor Center, and finally examine the collection at Gettysburg Museum of History.

Quickly create a custom-made itinerary for Gettysburg using our trip planner.

You can do a combination of flight and taxi from Pittsburgh to Gettysburg in 4 hours. Other options are to drive; or do a combination of flight and car. In August, daytime highs in Gettysburg are 83°F, while nighttime lows are 63°F. Finish up your sightseeing early on the 14th (Wed) so you can go by car to Hershey.

Things to do in Gettysburg

Museums Historic Sites Parks
Highlights from your plan

1
night
Hershey

Hershey ©
Home of the Hershey Chocolate Company, the town of Hershey is regularly referred to as the sweetest place on earth.
Start off your visit on the 15th (Thu): get in on the family fun at Hersheypark.

For photos, more things to do, and other tourist information, go to the Hershey itinerary planner.

Drive from Gettysburg to Hershey in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 84°F in August, and nighttime lows around 65°F. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Philadelphia.

Things to do in Hershey

Theme Parks
Highlights from your plan
Hersheypark ©
Hersheypark

2
nights
Philadelphia

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
Kick off your visit on the 16th (Fri): ponder the world of politics at Independence Hall, then admire the masterpieces at Philadelphia Museum of Art, and then admire the local landmark of Longwood Gardens. Get ready for a full day of sightseeing on the 17th (Sat): hunt for treasures at Reading Terminal Market, then explore the world behind art at Barnes Foundation, then get engrossed in the history at Eastern State Penitentiary, and finally don't miss a visit to Liberty Bell Center.

To find more things to do, photos, ratings, and other tourist information, use the Philadelphia journey planning website .

You can drive from Hershey to Philadelphia in 2 hours. Alternatively, you can take a train; or do a combination of taxi, flight, and train. In August, daytime highs in Philadelphia are 85°F, while nighttime lows are 69°F. Finish up your sightseeing early on the 17th (Sat) so you can travel back home.

Things to do in Philadelphia

Museums Nightlife Classes

Side Trip

Longwood Gardens
Highlights from your plan
Independence Hall ©
Independence Hall
Longwood Gardens ©
Longwood Gardens
Philadelphia Museum of Art ©
Philadelphia Museum of Art

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