The Lake County Forest Preserve has done a good job of building and maintaining launch areas along the Des Plaines, with a concentration in mid-county around Libertyville that make for good short canoe trips (kayaks can be a little tough in summer and fall, as the water level can drop to 6-12", not quite enough to get good bite from a paddle face. There is significant deadfall, depending on how rough the weather's been, though it's almost always passable with a little effort and moderate boat handling skills.
The water level in the Des Plaines is notoriously changeable and sensitive to whatever precipitation we've recently gotten. Always check with the Forest Preserve or the paddling shop Offshore (located next to the Route 60 launch in Vernon Hills) if you're unsure about conditions.
A good 60 to 90 minute day paddle calls for a put in at Oak Spring Road (just north of downtown Libertyville, and across the road from Lake Minear) paddling to the Route 60 launch, about 3.5 miles downriver. In early spring or at times when the water level's reasonably high, you can actually do this trip in something closer to 35 or 40 minutes - in mid-summer and beyond, when the water level's lower and current nearly non-existent, it'll take longer.
There are several check-dams along the length of the river, and when the water level drops, they'll need to be portaged around. NOT a big deal. Paddle over to the west bank of the river, pick the boat up, and drop it on the either side. When the water's higher, you don't have to worry about it, as the river flows right over the dams and you'll never know they're there.
This route travels through a combination of private home sites and forest preserve lands. Kids get a big kick out of paddling under the EJ & E train trestle across the river, which comes as a nice surprise. Occasional deer and other wildlife along the banks. Water quality's better than it was 30 years ago, though it's still a very muddy river - plan on doing a rinse-out when you get home.
The take out at Route 60 is a little sneaky if you've never seen it before. Just after you pass under the footbridge south of the road is a little passage in the bank. THAT's where you want to go, but be prepared to do a bit of poling to push your boat through the channel, as it has a tendency to be very shallow (3-4 inches) in all but the highest water. There's a paved parking lot with plenty of spaces for your pickup vehicle.
If you're thinking more of a round-trip, anytime mid-summer or beyond is an easy up and back. Put in at Rt 60 and head north (just portage around the first dam when you head north - the red markers on the lawn there are to indicate the area that's ok for walking the boat around), go as far as the kids will allow, and turn it around. Fall colors are excellent on this section of the Des Plaines, and highly recommend it as a short autumn afternoon getaway.
The Des Plaines flows most of the year around, and is particularly fun right after winter thaw (well, at least after those winters when we've actually gotten SNOW....).
Parking lot in both launch areas. No restrooms or fresh water, so bring your own. Rt 60 launch right next to River Tree Court strip mall, with some carryout restaurants/delis and Offshore, a paddling shop.
No fees, though all boats must have Illinois registration.
Oak Spring Road put-in - St Mary's Road north, past Rt 176 approximately 1.5 miles to Oak Spring Road. West on Oak Spring to launch. Also accessible from Milwaukee Ave (Rt 21), located just north of the Metra train tracks on the north side of downtown Libertyville.
Rt 60 canoe launch located 250 yards east of intersection of Rt 21 (Milwaukee Ave) and Rt 60. Approx 2 miles west of exit off I-94.