Chicago to Milwaukee Whether or not the East and West Coasts will ever admit it, we all know the Midwest has some pretty rad little cities, each with a vibe and pulse all their own. Chicago is smack dab in the middle of them all, giving the weekend getaway all kinds of potential. The closest destination is Milwaukee, less than a hundred miles away. If you’re a biker of any kind, be it avid or just in perfect weather months, you’ve probably at least thought about making the trip on two wheels from our side of the lake to the Brew City. Aside from great exercise, it’s the cheapest way to travel other than walk. The trip itself takes about eight hours without stopping (so about a full day for those of us not training for an Iron Man), and is somewhere between ninety-five and one-hundred-and thirty-miles depending on how closely you follow the lakefront. Paved or compacted limestone trails take you most of the way and what little bit of roadway biking there is is well marked. There are an infinite number of ways to do the trip, from Art Institute to Milwaukee Art Museum, or from Wrigley Field to Miller Park. Take a break for some boutiqueing in Racine or try and schmooze your way in at the Waukegan Yacht Club. If biking both ways in one weekend sounds too exhausting, you can always take the Metra home.
