nice tip too.. although its not likely i ever visit chicago, but i will enjoy to compare tracks with google street

If I remember well, the episode of Midtown Madness (I think it was the second) sold on the first Xbox took place in Washington.

The addons for Cities in Motion have real cities in them, I can only talk about Berlin there and although some streets are approximately in the right place, most has been left out. It's only a mutilated version of the central part of town which was quite a disappointment.

Micecraft has a lot of this stuff:
http://www.geeknative.com/37872/top-7-most-realistic-cities-in-minecraft/

Denmark was recreated in Minecraft by their government and this is what happened:
http://www.dailymail.co.uk/sciencetech/article-2623697/American-hackers-bomb-Minecraft-version-Denmark-raise-stars-stripes-cyber-attack-education-project.html

Lol, I still have it somewhere, it was a weird experience between movie and racing game.

The currently released Dirt Rally is modelled off real life tracks and circuits from Wales, Monaco, Germany, Sweden, Finland, Norway and Greece. Oh yeah and Pikes Peak too.

I recall Vette! was a racing game using a real model of an existing city.

http://www.mobygames.com/game/vette

"Race your corvette against another human or computer player through an accurate reproduction of San Francisco."

Microsoft Flight Simulator 98 had these. I suppose other "games" in the series did too, but this is the only one I own.

Was Shenmue based on real life locations?
I know the weather patterns were accurate to the timeline.

I actually can't remember if it was urban/rural location or just the open road.

maybe Klumpen0815 remembers :)

How come no one has said TRUE CRIME series of games?

I think it was the open road, will try again as soon as I find it again (which may take a while).

Test Drive Unlimited purportedly had realistic road system of one of the islands of Hawaii.

Doom 2 WAD featuring New York (haven't tried it myself): http://onemandoom.blogspot.com/2013/02/planisphere-2-planisf2wad.html

I've played both Getaway Ps2 games. As far as I've heard the city is pretty accurate, just heavily scaled down of course. Unfortunately they're Ps2 only.

The Gekokujo mod for Mount & Blade: Warband features an accurate map/world layout of that era of Japan.