Est. 1998
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Home Games Midtown Madness Midtown Madness
Midtown Madness
Midtown MadnessWindows 95/98Racing

Midtown Madness

Developer: Angel Studios · Published by Microsoft · 1999
The open city before open world was a genre.
Open WorldOnline MPRacingCity DrivingCops and Robbers
4.5
out of 5.0
Excellent
POCG VERDICT
Chicago has never been this fun to destroy.
Maniac wanted Carmageddon-style freedom in a real American city. Midtown Madness delivers Chicago in 1999, even if the stunt physics don't quite keep up.
About This Game

Midtown Madness is an open-world racing game developed by Angel Studios and published by Microsoft, released for Windows on May 18, 1999. It was one of the first racing games to place players in a freely explorable city environment rather than a fixed track, using downtown Chicago as its setting. The game modeled Chicago at a simplified but recognizable scale, including major thoroughfares, elevated train sections, landmarks, and the river bridges, all populated with civilian traffic that obeyed traffic signals.

Players choose from nine vehicles ranging from a Volkswagen Beetle and Ford Mustang to a city bus and Ford F-350, each with distinct handling characteristics. Four game modes were included: Cruise (free roam), Timed Race (checkpoint racing against the clock), Checkpoint Race (live-city racing against opponents with open route choice), and Circuit Race (closed blocked-off course against opponents). The game supported both single-player and online multiplayer via the Internet Gaming Zone, including a Cops and Robbers mode in which teams competed to recover a gold bar and return it to their base.

Midtown Madness was notable for its physics and civilian AI systems, which were ambitious for the era. Civilian cars responded to collisions and traffic signals, pedestrians jumped clear of oncoming vehicles, and police units attempted to intercept rule-breaking players. The game drew frequent comparisons to Carmageddon for its free-driving tone, though it emphasized racing over destruction and carried an ESRB Everyone rating.

The game received generally positive reviews at launch and spawned two sequels: Midtown Madness 2 (1999, adding San Francisco and London) and Midtown Madness 3 (2003, Xbox exclusive, set in Washington D.C. and Paris). The original game was never officially re-released on any digital storefront and has no current legal distribution channel.

POCG ReviewOriginal: May 18, 1999
4.5
Excellent
Review Verdict
Midtown Madness
Maniac wanted Carmageddon-style freedom in a real American city. Midtown Madness delivers Chicago in 1999, even if the stunt physics don't quite keep up.
In the News3 mentions
May 101999
Microsoft Announces E3 Lineup
Microsoft today unveiled the lineup of games and gaming devices it will showcase at this year's Electronic Entertainment Expo (E3) at the Los Angeles Convention Center May 13-15.
Release
Apr 211999
Midtown Madness gone Gold
Midtown Madness has crossed the line from waiting game to actual product, which is always better than another promise.
Release
Apr 161999
Ford vehicles in Midtown Madness
Today at the 35th Anniversary of the Ford Mustang event, Microsoft revealed it has reached an agreement with Ford Motor Co. to feature a selection of licensed Ford vehicles in the new Midtown Madness racing game for the PC from Microsoft.
Release
How to Play TodayYour options for running this game in 2026
Original Hardware
Requires a Windows 9x or compatible PC. Original CDs available on eBay for under $10.
Modern Re-release
No official re-release. Never appeared on GOG, Steam, or any digital storefront.
Emulation / Other Options
Runs on modern Windows via compatibility mode or a lightweight VM. Widely available through abandonware sites.