It’s the Windy City, Second City, or whatever else you want to call it. Home of the Bears, Bulls, Blackhawks, White Sox, and the first-place Cubbies, it has hundred-degree summer days, winters with 10-foot snow drifts, Willis Tower, the Art Institute, and some of the best steak houses in the country. But, rust be damned, the Midwestern city also has an incredible car culture, and with a few minutes to kill, you’re likely to find your dream machine on Craigslist Chicago.
Are you a Japanese car guy? Great. Prewar collector? Perfect. Muscle car freak? Even better. Being the biggest city around (sorry Detroit and Milwaukee), the Chicago Craigslist has something for everyone — and it completely sucked us in while “researching” this article.
From vintage world-class exotics to wild off-roaders, here are six of our favorite finds on Craigslist Chicago.
1. 1985 Ferrari 308GTSi
Unfortunately, no one is selling a 250GT California Spyder in the Metro area. But if you really want to channel your inner Ferris Bueller, there’s this 308GTSi, resplendent in all its ’80s glory. A few years ago, all those louvers and the white over red color combo would’ve turned serious collectors away. But time has been kind to the 308, and this 13K-mile example’s $75,555 asking price is a fair one — hell, it’ll probably seem like a bargain in a few years. You could buy this one and keep it in a vault; it’s only going to appreciate in value.
2. 1926 Pierce-Arrow Series 80 Convertible
There may not be much to go on in the listing — OK, there’s nothing going on other than the model and price — but it’s tantalizing nonetheless. From 1901 to 1938, Buffalo, New York-based Pierce-Arrow was one of the most prestigious automakers in the world, mentioned alongside Rolls-Royce, Mercedes-Benz, Duesenberg, and Packard. The Series 80 was the “affordable” Pierce-Arrow, selling for around $4,000 at a time when the Model T Ford started at $380. They’re extremely rare in any condition today, and at $39,900, this one could be a steal. We wouldn’t try to make this one a daily driver, but if you’re looking to join the Concours set, this is probably a good place to start.
3. 1990 Nissan Skyline GTR R32
Like with any local Craigslist, typing the letters “JDM” (Japanese Domestic Market) into the search bar usually brings up a horrifying amount of rusted out, slammed Civics, Corollas, and Imprezas. But every now and then you come across a gem, like this gorgeous near-stock Skyline. If you don’t already know, the Skylines are the ultimate JDM forbidden fruit: a performance car legend that stayed in Nissan’s home country until the U.S. Department of Transportation allowed for the import of cars 25 years and older a few years back. Now, anyone with a little cash and a dream can own one, and you’d be hard pressed to source, buy, and import a Skyline as nice as this one for under the $26,900 asking price.
4. 1969 Chevrolet Corvette
By now, even non-running early C3 Corvettes are fetching five figures, which is what makes this one so intriguing. Yes, it has an early ’80s nose awkwardly grafted onto it, but the fender grilles and rear end make it look like a legit ’69. Provided it does actually run great, and doesn’t have any structural damage or rot lurking underneath, it looks like it could be a bargain for $13K/best offer. You can drive it while you fix it, but we wouldn’t recommend taking it to any Corvette shows until you get the bodywork sorted out. Corvette guys can be vicious…
5. 1971 Toyota Land Cruiser
So what if immaculately restored FJ40 Land Cruisers fetch upwards of $100,000 at auctions today? This well-loved ’71 Land Cruiser may have lost its original inline four, but it’s been replaced with a recently rebuilt small-block Chevy V8. We don’t love the woodland camo paint, but like the aforementioned Corvette, this one can be driven and properly off-roaded while you upgrade it or put it back to stock. And at $8,000, it proves that there are still deals to be had on the vintage Land Cruiser market.
6. 1982 Porsche 911 Targa
A few years ago, projects like this needy 911 Targa for $19,500 were fairly commonplace. Today, they’re few and far between. Nearly $20K may sound like a lot for a project, but with a little work, this solid running 911 could be enjoyed for years and sold for a profit, which seems to be the plan for most vintage Porsche owners.