Craigslist Chicago: 10 Cars Al Capone May Have Driven

Al Capone's booth
Al Capone’s booth at the Green Mill | Source

Chicago, Chitown, The Windy City. Home of ‘Da Bears, ‘Da Bulls, the White Sox, Cubbies, and former home of Al Capone. With more than 10 million residents, the Chicago metropolitan area has a rich and varied history to rival that of any city in the United States. Despite the passage of time, everyone likes to talk about the organized crime history of the city. Some even collect gangster memorabilia. To do that, they often spend hours searching Craigslist Chicago for rare or interesting finds.

As we all know, Craigslist is a veritable cornucopia of the unique, interesting, and bizarre. You can shop for, buy, sell, or discuss nearly anything. Granted, there are a few limitations: illegal drugs and guns are off limits; but other than that, shoppers can find almost anything.

Craigslist Chicago: Gangland cars come to life

Organized crime ran nearly every large city in the United States at one point or another. For Chicago, the peak of the mob’s power may have been during the Prohibition Era. The period between 1920 and 1933 was a financial boon to those willing to ignore the law. Despite federal restrictions, alcohol flowed and underground clubs called speakeasies flourished. One of the controlling figures of the time was Alphonse Gabriel ”Al” Capone. Capone was a man known for his personal style and viciousness. His gang was known for their sleek, fast cars and a ruthlessness that rivaled that of their boss. Just thinking about the man, the speakeasies, and the cars is enough to make you wish for a time gone by.

The era often makes people wax nostalgic. It was a time when Americans were carefree, drove fantastic cars, and enjoyed itself with abandon. One way to bring some of that nostalgia to life is to buy a car from the period. Many Chicago residents already have the car of their choice at home, but others are still searching. One of the best places to search for a car from the Prohibition Era is Craigslist Chicago.

There are hundreds of pages to be searched. For some of the more interesting finds, keep reading.

1. 1933 Ford Victoria

1933 Ford Victoria
1933 Ford | Source: Craigslist Chicago

Commonly called a Ford ”Vickie,” the Ford Victoria was a fairly common car of the time. They would have been powered by a 221 cubic inch Flathead V8. This model has been updated with a ”Chevy 350 with a mild cam,” among other things. The updates should make this a fun to drive car that Al would have enjoyed.

2. 1926 Ford

1926 Ford
1926 Ford | Source: Craigslist Chicago

By 1926, the Ford Model T dominated the countryside. Thousands upon thousands had been sold. Today, a large portion of them have been turned into street rods, but not this one. This is an excellent example of an all-steel body with many updates so that it can be a parade machine or a weekend driver.

3. 1929 Pontiac

1929 Pontiac
1929 Pontiac | Source: Craigslist Chicago

General Motors introduced the Pontiac brand in 1926 to compete in the economy section of the automobile market. It was supposed to be a companion to GM’s Oakland brand, but quickly outsold Oakland, eventually replacing it. Featuring powerful six-cylinder engines, you can almost see a group of gangsters pulling up to the curb in this four door.

4. 1927 Ford T-Bucket

1927 Ford T-Bucket
1927 Ford T-Bucket | Source: Craigslist Chicago

It is getting harder and harder to find an early Ford in original condition. One of the most common modifications of the Ford Model T is the T-Bucket. This listing has a fiberglass body, a 350 cubic inch Chevrolet small block, and dual Holley carburetors. The build list goes on and potential buyers can watch a video of the car in action.

5. 1932 Ford Hotrod

1932 Ford Hotrod
1932 Ford Hotrod | Source: Craigslist Chicago

Even when builders opt to let their Ford look original, you can bet it isn’t underneath. This seller is offering a 1932 Ford that was professionally built. The engine size isn’t listed, but it does feature a 350 Turbo gearbox, suggesting a Chevrolet engine.

6. 1927 Ford

1927 Ford
1927 Ford | Source: Craigslist Chicago

This 1927 Ford hotrod offers quite a few upgrades. According to the seller, the build features a ”fiberglass roadster body, channeled, 350 Chevy, 5 speed transmission, 4 wheel disc brakes, HEI, 50 Pontiac rear LED’s, low miles since build.” That is more than enough to justify the $10,000 asking price.

7. 1924 International Harvester SL

1924 International Harvester SL
1924 International Harvester SL | Source: Craigslist Chicago

Capone and crew had to get all of that booze delivered somehow. The only way to do that was by truck. Ford may have dominated the market, but International Harvester offered a sturdy pickup of its own. This model features a GM140 ”Iron Duke” engine, perhaps one of the most durable engines from the 1920s.

8. 1932 Ford Truck

1932 Ford Truck
1932 Ford Truck | Source: Craigslist Chicago

As with all things automobile in the 1920s and 1930s, Ford was in command. Its trucks carried freight to every city in the United States. Many trucks have been turned into hotrods, just as this one has. The owner says there are only 450 miles on a custom build that has a sheet too long to list. This could be a great bargain find for the right buyer!

9. 1930 Ford Model A Ratrod

1930 Ford Model A Ratrod
1930 Ford Model A Ratrod | Source: Craigslist Chicago

By definition a ratrod is a hotrod that is intended to look unfinished. This is a perfect example of that. If you don’t know what you are looking at, you would assume this one is ready for the scrap pile. Once you read the build sheet, you may still wonder. This is a project truck for a discerning home mechanic, but it is perfectly priced at just $3,750.

10. 1924 Studebaker

1924 Studebaker
1924 Studebaker | Source: Craigslist Chicago

This car was built as the height of the Prohibition Era was ending. Congress repealed the Volstead Act and the Eighteenth Amendment by December of 1933, just as the 1934 model year was beginning. Capone and most of his gang were already gone, bringing an official end to a decadent period in American history. This offering reflects the nostalgia for the era: a great bit of history just waiting for the right person to restore it!