25 days in Chicago Itinerary

25 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

This plan was created by another user.  Make it your plan

Route & dates

View / edit route

— 24 nights


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Shedd Aquarium as well as Adler Planetarium. Step out of the city life by going to Lakefront Trail and Silver Beach County Park. The Art Institute of Chicago and Chicago Cultural Center are good opportunities to explore the local culture. Get out of town with these interesting Chicago side-trips: Saint Joseph (Silver Beach Carousel & Lions Park Beach), Lake Geneva (Geneva Lake Shore Path & Geneva Lake) and Milwaukee (Milwaukee Art Museum, Historic Third Ward, & more). Spend the 5th (Sat) exploring nature at Indiana Dunes National Park. There's much more to do: make a trip to The Magnificent Mile, contemplate the waterfront views at Lake Michigan, paddle through the water with a kayaking and canoeing tour, and see the interesting displays at Volo Auto Museum.

For photos, maps, traveler tips, and more tourist information, read our Chicago route builder app .

Expect a daytime high around 78°F in September, and nighttime lows around 61°F. Finish your sightseeing early on the 19th (Sat) to allow enough time to travel back home.

Things to do in Chicago

Parks Outdoors Museums

Side Trips

Milwaukee, Saint Joseph, South Bend, Lake Geneva, Utica
Highlights from your plan
Lake Michigan ©
Lake Michigan
Silver Beach County Park ©
Silver Beach County Park
Starved Rock State Park ©
Starved Rock State Park