8 days in Chicago Itinerary

8 days in Chicago Itinerary

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Route & dates

8 days in Chicago Itinerary

Start: Philadelphia
Drive:  12​h 30​min
1
Chicago
— 7 nights
End: Chicago

7
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of the city life by going to Kayaking & Canoeing and Matthiessen State Park. You'll visit kid-friendly attractions like Silver Beach Carousel and Discovery Center Museum. Change things up with these side-trips from Chicago: Indiana Dunes State Park (in Chesterton), Starved Rock State Park (in Utica) and Indiana Dunes National Lakeshore (in Porter). There's still lots to do: trek along Geneva Lake Shore Path, grab your bike and head to Lakefront Trail, ponder the design of Buckingham Fountain, and sample the fine beverages at Copper Fiddle Distillery.

To see ratings, where to stay, maps, and more tourist information, use the Chicago trip planner .

Philadelphia to Chicago is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. You'll gain 1 hour traveling from Philadelphia to Chicago due to the time zone difference. In June, plan for daily highs up to 81°F, and evening lows to 63°F. Finish your sightseeing early on the 7th (Sun) so you can travel back home.

Things to do in Chicago

Parks Nature Outdoors

Side Trips

Lake Geneva, Saint Joseph, Utica, Indiana Dunes National Park, Copper Fiddle Distillery
Highlights from your plan
Kayaking & Canoeing
Silver Beach County Park ©
Silver Beach County Park
Starved Rock State Park ©
Starved Rock State Park

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