Chicago Nightlife: The Ultimate Guide

FSD Staff

The speakeasy vibe of Chicago is still alive and well in many of the city’s key nightlife destinations. 

Whether you’re looking for live music, bars serving craft cocktails, casino action, stand-up comedy, or a pumping nightclub where you can dance the night away, Chicago has you covered. 

Here are just a few of the best venues that you’ll want to consider visiting.

Green Mill

If you want to soak up a little bit of history and enjoy some of the finest live music in all of Chicago, you’ll want to pay a visit to one of the city’s oldest clubs, which was once a speakeasy during the time of prohibition: Green Mill. 

Opened in 1907, the legendary Green Mill was once frequented by the notorious gangster Al Capone. In fact, you can even sit in Capone’s favorite booth.

The live music is the main pull at Green Mill, though. Each night, you will find live performances from both local and big-name jazz artists that go on until the small hours.

The Second City

Comedy fans are sure to want to spend a night at one of Chicago’s many comedy venues. If you only get to visit one, make sure it’s The Second City.

Today, you’ll find performances by many up-and-coming stand-up comedians, but the venue is also steeped in comedy history.

The birthplace of improvisational comedy has been going for more than half a century, and in that time, The Second City has seen performances by legends like John Belushi, Dan Aykroyd, Bill Murray, Tina Fey, and Steve Carell. 

The Violet Hour

Cocktail lovers will enjoy spending an evening at the acclaimed Violet Hour bar. The venue’s wide range of cocktails includes delicious beverages like Gemini Sky, Little Black Dress, and More Irish Than Catholic.


There’s also a superb selection of wines, beers, and spirits. But the cocktails are what most people come to sample. The Violet Hour is a pioneer in Chicago’s craft cocktail community, so you’ll be able to try seasonal favorites no matter what time of year you visit.


There’s just one rule you need to abide by when entering the ambient and atmospheric place: no cell phones are allowed. 

Rivers Casino Des Plaines

If you’re a fan of casino games like blackjack, craps, poker, baccarat, roulette, and slots, you can always check out the latest casino bonuses at online casinos and play on the web.

Alternatively, you can play the same games in the flesh at Rivers Casino Des Plaines, which is one of the best casino resorts in the Chicagoland area. 

It boasts more than 1,000 slot machines and video poker machines and has plenty of table games available. You can also engage with sports betting at the Rivers Casino Des Plaines.

In fact, even if you’re not much of a fan of casino games, you can still enjoy a night out at this establishment. It has no less than six restaurants and often puts on live entertainment.

Furthermore, it is currently being expanded to provide a ballroom, a 24-table poker room, and another restaurant. Though, if you’re after the best dining in Chicago, you should consider visiting one of these top ten restaurants.


Chicago is home to some amazing nightclubs, so if you want to dance till dawn, no matter what your music preference is, you’ll find a club to suit your tastes. One of the best clubs for DJs pumping out house and techno tunes is Sound-Bar.

There are various dance floors and seven bars, as well as a solid lineup of resident DJs. So, for an unforgettable, energetic, and uplifting night, put on your dancing shoes and head to Sound-Bar.

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