You don’t have to go too far out of the city - more than 10% of the county land area is forest preserve. Inside the city, the far northwest side (along the river) and the far south side (big marsh/beaubien woods) are probably the best bets.
I know that the wooded section between the IC tracks and LSD from 47th street up to Oakwood/Pershing is a hiking trail very popular with birdwatchers. You can keep walking up to the 31st street beach parking lot, but I think it might technically be trespassing ;)
Naturally, if you want really good hiking, there is a daily train from Union Station that stops at the front gate to Glacier National Park. You can also take the South Shore train eastwards - there are 3 stops adjacent to the Indiana Dunes (both the state and national parks).
No problem. You know, the whole area is very flat. There’s no getting around that, and some people will never accept that any hiking trail can be good if there isn’t a lot of elevation change. That’s their loss.
I remember going to a talk at the cultural center ~10 years ago where some lady, who was apparently very famous in her line of work, talked about moving to Chicago because of her husband’s new job and spending many years hating the natural surroundings. Until one day she was in a prairie west of the city and decided to really look at the wildflowers. And that was the spark that got her to start drawing the flowers, and eventually made her famous for it.
Anyway, it’s no Coastal California or Colorado mountain meadow. But if you go out and explore with a desire to find beauty in it, you will :)
Edit - and by the way, on the South Shore train, Dune Park and Beverly Shores have trails you see from the train platform. Ogden Dunes is a bit trickier, the open space west of the train station is all national park service land, east is private property except closer to the lake. The town itself tries very hard to make it look like a private gated community but the roads are all public and you are free to walk right in. Miller Beach I’d say the train is too far from the parkland, but if you have a car, the area due north starting about a mile from that train station will blow apart every stereotype you’ve ever had about Gary, IN.
Hah, there's my only lament about Chicago: no pet-friendly public transit if you have a large dog. I don't really have the stomach for the loopholes either: service dog lies or carrying her in a duffel bag NYC subway-style.
I know that the wooded section between the IC tracks and LSD from 47th street up to Oakwood/Pershing is a hiking trail very popular with birdwatchers. You can keep walking up to the 31st street beach parking lot, but I think it might technically be trespassing ;)
Naturally, if you want really good hiking, there is a daily train from Union Station that stops at the front gate to Glacier National Park. You can also take the South Shore train eastwards - there are 3 stops adjacent to the Indiana Dunes (both the state and national parks).