Originally Posted by fayjairay
thanks guys, i appreciate the advice, but i am still not sure about the route to take. the website doesn't give a direct route from chicago to milwaukee. i drive up to milwaukee about twice a month, so i figured a ride would be a nice change.
It depends on what you like and what/how you ride.
I've never ridden south of Waukegan, but from Waukegan to Milwaukee there is a nice mix of trails and roads for slower (<15mph) riding featuring the McClory trail and the MRK trail, along with city streets that keeps you close (0-3 miles) to the lake, but it features a lot of moderately packed crushed limestone - not so nice on 23mm or 25mm tires. There's a book available in many stores in Chicagoland and metro Milwaukee called Biking on Bike Trails Between Chicago & Milwaukee
by Peter Blommer that details this route.
If you like to go fast on the open road, I'd go inland a bit to Hunt Club Rd, crossing the state line at Kenosha Cty MB and winding north on that until State Hwy 142, turn left going west to US 45, turn right going north to State Hwy 20 - keep straight as US 45 goes left staying on Colony Ave/108t St to Cty G, then go right to Cty V, turning left on V, taking V north to the Oak Leaf trail (aka Drexel Ave at that point) - then you can go east or west on the Oak Leaf Trail (a mix of paved multi use trails and wonderful wide go-fast parkways) depending on your destination.