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Starved rock is always nice.
Starved rock does allow dogs on leashes, though I've never brought mine because he likes to terrorize children. Just Google starved rock, it's a state park, you'll easily find the website with trails, directions, etc.
If you’re looking for something closer, the Swallow Cliff in Palos Park is a decent alternative.
Western burbs - Kane county has some great forest preserves. Check out Campton Hills forest preserve. ~75 mins or so from the city
Hike the Austin neighborhood!
Veteran Acres in Crystal Lake. Deer Grove West in Palatine. The Des Plaines River Trail stretches from the Wisconsin border down to near the city
Starved Rock, Devils Lake, Indiana Dunes
South Side