First Class Chicago makes pairing history with a Chicago vacation rental an incredible experience. Staying in an historic brownstone pairs architectural history with Chicago’s gangster background like fine wine and cheese. Whenever you think of Chicago you cannot help but think of Al Capone’s own ‘gangster squad‘ and the history tied to the Prohibition Era. In fact, to come to Chicago and not enjoy these sites robs you of a piece of what made Chicago the city it is today. All the memorable names in gang history were here.
Visit the Biograph
In 1934, John Dillinger, the most prolific bank robber in human history, was shot at the Biograph Theater in Chicago. Even today when you approach the old Biograph, now the Victory Gardens Biograph, you can’t help but be transported back to another time. The same Marquee stands in front of the same building that stood during Dillinger’s day. Made of red brick, the Biograph Theater is one of the only remaining examples of early Chicago theater design. It is an architectural icon unto its own. The inside of the theater was recently modernized so now you can take in a play in a historically significant monument.
The home where Al Capone lived with his family for many years, still stands on 7244 South Prairie Avenue. Or for the real enthusiast, you can go down to the site of the infamous St. Valentine’s Day Massacre which took place on February 14, 1929. Al Capone’s mob, dressed like police officers, lined up men of the North Side Gang and executed them. The garage where the massacre occurred, which stood at 2122 N. Clark Street, was demolished in 1967. In stark contrast to this violence is the grassy, shaded parking lot for a retirement home that remains.
Speakeasys – the Original Gangster Hangouts
Mere steps from one of First Class Chicago’s historic brownstones is the adventure of enjoying a cocktail in a former speakeasy. Chicago is full of them. During prohibition, Chicago would not be forced dry. These underground and illegal establishments blossomed in every neighborhood of historic Chicago. The Green Door Tavern , so named because restaurants with green doors told their patrons that there was a speakeasy inside, still exists as the oldest Chicago tavern. 
In the heart of the Chicago Loop you can also sip a Dry Gin Martini at the Exchequer Restaurant and Pub which was famous for being one of gangster Al Capone’s favorite hangouts. Check out a full list of former speakeasy pubs.
Take A Gangster Tour
If you don’t want to do all the research on your own, a fun option suited for those of you staying in either of First Class Chicago’s famous historical Brownstones or one of our high rise apartments is a Chicago Gang Tour. Untouchable Tours provides fun, no hassle tours of all the memorable Chicago gangster spots.
Be a part of history when you put yourself in the locations where bullets rang out in the night and where bars were raided and hundreds of gallons of alcohol seized. Go back to 1920 – 1930s Chicago when you stay at a First Class Chicago vacation rental in our Historic Brownstone and explore Chicago’s fascinating gangster history.
Choosing First Class Chicago allows you the opportunity to experience a Chicago Brownstone on your own. You can stay in an exquisite Gold Coast Chicago Brownstone with all the history on the outside, completely remodeled on the inside. We offer two one bedroom/one bath options, one on the 
There are so many amazing farmers markets in Chicago. You can enjoy all they have to offer when you choose Chicago vacation rentals. If you opt for a traditional hotel experience, you get to walk around these farmers markets but you cannot really taste, experience and enjoy the many flavors found there.
However, when staying in a Chicago vacation rental, you can also enjoy a year round farmer’s market right near your rental in downtown.
I’m sorry, but size does matter when it comes to where I’m staying when I go on vacation. I’ll never forget our honeymoon when we stayed at this “boutique” hotel in the middle of Paris only to be disappointed how spatially challenged it was. The “elevator” was about the size of a vertically oriented coffin so I had to shove all our luggage in it, press the 3rd floor button, and then run up the circular stairs to try and meet it at the top before the doors closed on me with my luggage still in the elevator. Once we got to our room, it was one of those shoeboxes where you could potentially pull out the dresser drawer and accidentally hip bump your partner out of the window. The bathroom was a shower- toilet-sink, all in one closet contraption so that EVERYTHING was wet after you took a shower. Good times…
Chicago vacation rentals are about living like a local instead of living like a guest. Whether it’s a Chicago vacation rental brownstone or highrise condo, it’s about the privacy, the personal experience, the amenities, the ability to cook if you want, the occasion to open that specially selected bottle of wine while watching the people stroll down a tree-lined neighborhood street, and most of all… the room to share it all with family or friends.