Just outside of Chicago, Black Oak Trail at Little Red Schoolhouse Nature Center is a great loop trail for beginners and is family friendly.
The trails traverse a rolling glacial highland of oak woods and prairie. The hiking trails connect to miles of multi-use trails where you can hike, mountain bike, cross country ski and snowshoe. Lastly, there is an interpretive center with exhibits about local nature and history.
The trailhead starts just west of the Farm Pond Trail and interpretive center and loops for 2.6 miles through a wooded forest preserve. This trail is beginner and family friendly, but dogs are not permitted. Come early to beat the crowds.