Chicago is one of the cities vying for the 2016 Olympics. If chosen, their organizers have already struck a deal with Wisconsin to hold the road and mountain bike races in Wisconsin. Specifically the area around Madison and Mt. Horeb, Wisconsin, where I live and work.
The Road Race course would begin on the University of Wisconsin campus, just blocks from my office. It would then wind out through Mt. Horeb and around Blue Mound State Park, where I ride the Military Ridge Trail frequently. This course would likely run within 5 miles of my house.
The Mountain Bike Course would be carved out of the Tyrol Basin ski course, which is just a few miles outside of Mt. Horeb.
This area is already home to several significant races every year, including the:
Wisconsin Ironman http://www.ironmanwisconsin.com/bike.html
Horrible Hilly Hundreds: http://www.horriblyhilly.com/course.html
Dairyland Dare: http://www.dairylanddare.com/routes.php (roughly 22,000' of climbing over 300k course)
The entire area around Mt. Horeb and Blue Mounds is quite hilly. No huge climbs, the tallest climb is just over 900', but it is a sea of rollers. All of which I avoid by riding the rail trail.
However, I don't plan to still be living here in 2016, so even if Chicago lands the Olympics, I'll have to come back to visit if I want to see any of these events.