Midtown Madness (1999) nostalgia in GTA 5 Chicago. 5 Chicago Downtown opponents in a race to the finish. Race takes place in the urban streets of Downtown Chicago. Start at Lake Shore Dr, full circle of the race takes you along Wacker Dr all the way to Millennium Park and back to Trump Tower. Passing by Marina City tower the race goes under into 233 North Michigan complex tunnel. The race then circles back after crossing the Michigan river and heads back to Lake Shore Dr.