Chicago was the city featured in the original Midtown Madness. On August 9, 2014, a conversion of Chicago was developed for Midtown Madness 2 by SuperSecret, in which it is now possible to cruise and race on it. This track features the same races from the original Midtown Madness, with working opponents. All of the famous landmarks seen in Midtown Madness are now present in this conversion for Midtown Madness 2. In addition, the race menu and loading screens feature accurate race maps, and are now in MM2-style, and the Chicago Police Ford Mustang Cruiser is now a separate, usable vehicle.
It can be downloaded here.
- Chicago was mentioned in Midtown Madness 2 by a London traffic driver asking: "Are you from Chicago!?" It could mean the player is originally from Chicago, or it is just a reference to the original Midtown Madness because it has no storyline.