Chicago River
This may be the best downtown urban paddle in the country! By heading up the Chicago River in a kayak, you pass some of the largest and most interesting buildings that Chicago has to offer. As you paddle you also pass under f... trails.com
Thatcher Woods
The trail is singletrack for the majority of the distance. The main body runs along the Des Plaines River and has a fair assortment of technical aspects including fallen trees, small hills, creepy underpass and tight co... singletracks.com
North Shore Channel Trail
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but the last 0.25 mile runs alo... traillink.com
Indian Road Woods
This is a nice option for those in the city who are seeking some singletrack close by. The trail basically follows the river with a parallel trail on the higher ground above the flood plain for at least part of the way.... singletracks.com
Skokie Lagoons
Surrounded by urban development, the islands and the scenic waterways of the Skokie Lagoons provide a wooded refuge just 15 miles north of the Loop. After skirting the southern edge of the lagoons, this route delivers you to ... trails.com
Swallow Cliff Woods, Lagrange, Illinois
Located at the Palos Forest Preserve off IL 83, 0.5 mile west of US 45. If you follow the main gravel loop, about a seven-mile trip, you'll ride along a wide, quiet trail used by joggers, hikers, and equestrians. The woods al... trails.com
Cambr Mountain Biking Trails
Most trails here are single-track, but there are several multi if you want. Roughly 50 miles of trail are available between the orange, yellow, tan, red, brown, blue, and green trails. PLEASE do not ride the trail... backcountrysecrets.com
Illinois Prairie Path, Maywood, Illinois
The eastern trailhead is at 1st Avenue in Maywood. The Wheaton intersection point, the middle, is often considered the starting point. The trail's branches take you to Aurora, Batavia, Geneva, and Elgin. This 122-mile total o... trails.com
Maple Lakes
Located at Palos Forest Preserve off IL83, 3 miles west of US 45. This 12-mile loop is a little longer and slightly more difficult than the Swallow Cliff loop. It passes around six sloughs and a couple of lakes. Several other... trails.com
Polecat Creek Trail
This is a very simple trail looping through Hedge (Osage Orange) and Hickorys. It runs fast along the creek bank offers simple dodges through the trees. Don't plan for this to be the only trail you ride, rather add it a... singletracks.com
Salt Creek Wine Bar
Best singletrack is generally on the South/West side of the creek until Mannheim Road, then take the paved trail South and West until you reach the Bemis Woods trail network, or continue on into DuPage County and check out F... menuism.com
Palos Hills
Several miles of trails with varying difficulty, tough singletrack, log jumps, steep climbs and downhills. some trails are shared with equestrian riders. singletracks.com
Waterfall Glen
At the glen, trails are 8 feet wide, white-tailed deer are plentiful, and a scattering of pine groves planted long ago by the federal government offers constant changes in color and composition. Though some bikers pedal along... trails.com
Deer Grove, Palatine, Illinois
Located in Palatine, off Dundee Road. If you're north of Chicago, Deer Grove is where you should go to get some mountain bike action. While there is a paved bicycle trail in the forest preserve, the real excitement is on the ... trails.com
Cipilly Woods Trail
A great trail. Starts off with a downhill that you wouldn't expect from a trail in the Chicago area, then switches to up and downs. A couple river crossing(very deep when wet) and very tight singletrack near the river w... singletracks.com
Messenger Woods
there are some low lying areas so be sure to ride spikes. its okay to go off the beaten path, most of the deer paths link with other little known trails singletracks.com