Chicago has developed a reputation as one of he best big cities for cyclists, thanks in large part to long-standing support from city government for cycling opportunities. The city now has more than 200 miles of on-street protected, buffered and shared bike lanes. Plus you’ve got the Lakefront Path, perhaps the most cyclist-friendly urban trail in America. It features 18.5 uninterrupted miles from one end of the Chicago to the other with great views of the city skyline and Lake Michigan at your side the whole way.
The Des Plaines River Trail encompasses a lot of space, serving as one of the longest trails in the Chicago area. There are some gaps in the system, but if you’re willing to take some surface roads, the trail will take you from River Grove in the near western suburbs all the way to the Wisconsin border.
For a family-friendly option, the Bemis Woods Forest Preserve in Western Springs serves as a great starting point for the seven-mile paved trail that will take riders to the Brookfield Zoo along the Salt Creek Trail, with plenty of amenities along the way.