A commenter proposes the more direct course.
Passenger rail used to run from Madison through Milwaukee to Chicago, but was killed off, like so much train service in the US.
Telling media, Olympic visitors and competitors to come to the games in Chicago, then take the train to Milwaukee before switching to a bus or rental car to get to Madison will make Wisconsin look bush league.
A few years ago, Amtrak got as close as the south side of Janesville, on a schedule designed for the convenience of the Chevrolet factory. The Milwaukee Road had a three hour timing, with eight intermediate stops, up to April 30, 1971. The North Western had a two hour thirty minute timing in the summer of 1954, with stops in Beloit and Janesville. Although the midwestern high-speed rail wish list includes Chicago-Milwaukee-Madison-Twin Cities, running the Olympic service, if any, by way of Milwaukee is going the great way around. The Milwaukee Road gave up on that routing well before Highway 30 became Interstate 94.
At least they should be able to get a 2 hr 15 Madison to Chicago train into place in 7 years. The Chicago and Northwestern [c.q.] Railroad 400 trains made this haul in that time frame 60+ years ago.
If we can't run trains at least as well as in the 1940s, it will prove we are unworthy of hosting the Olympics.