By far the best hike or walk in Chicago is along the lakefront on the Chicago Lakeshore Path which takes you from beaches to harbors and a variety of scenic sights. This link provides you with exactly what to expect on each section of the path. Hiking and Walking Trails In or Near Chicago
1. Chicago Lakeshore Path
2. Beverly Lake Forest Preserve – Hoffman Estates – Illinois Highway 72/Higgins Road -the cross country ski trails, not the turnoff that goes around the lake – 5 mile trail – moderate- Map
3. Cap Sauers and Swallow Cliff Loop Trail – Palos Park, Illinois – Best known for its 100-foot bluff and demanding stair workout. There are 8 miles of trails, unpaved and 800 acres.
4. Starved Rock State Park – 2668 E. 875th Road, Oglesby, Ilinois 61348 – 99 miles or 1 hour and 38 minutes from Chicago but has more natural feel with waterfall, land and water cruises, and events. It has been Voted the #1 attraction in the state of Illinois. There are 13 miles of trails, plus fishing. There are guided hikes, half day hikes with the Walker’s Club (call 800-866-7625) and self-guided hikes. Plus Hike and Lunch guided hikes. Trail Maps
5. Morton Arboretum – 4100 Illinois Route 53, Lisle, Illinois 60532. Open 7am to sunset. Costs $12 for adults except Wednesdays when it is $8, $11 for seniors ($7 on Wednesdays), kids 1-17 – are $9, $6 on Wednesdays. Lisle is 26 miles from Chicago.
6. Lake Katherine Nature Center and Botanical Gardens – 7402 West Lake Katherine Drive, Palos Heights, Ill. 60463 
7. Bloomingdale Trail and Park – runs along an unused elevated trail line along Bloomingdale Avenue from Ashland to Ridgeway. Runs 2.7 miles through Chicago NW neighborhoods. Consider this a city trail.
8. Garfield Park Conservancy – 300 North Central Park, Chicago, Ill. 60624- damaged from storm so confirm before going.
9. North Park Village Campus and Nature Center – 5801 N. Pulaski Road, Chicago 60646 – Open 10am to 4pm. Hiking and birding areas plus a nature center.
10. Indiana Dunes – 1215N. State Road 49, Indiana 46304. 15 miles of beach on the southern shore of Lake Michigan. 15,000 acres. Open from 7am to 30 minutes past sunset. Hikers and bicyclists can enter at 6am. $6 to park.
11. Matthiessen State Park – Route 178, North Utica, Illinois 61373. Five miles of surface hiking trails. Map 
