Bar Experiences in Chicago

Chicago has a great bar scene. You can visit dive bars, fancy bars and bars with great food and fascinating people. Some bars are great to go to at certain times; others you can stop in at any point and have something interesting happen. Chicago offers bar lovers a little bit of everything anyone could ever want.

Whether you are staying in Chicago for the first time, are a regular visitor, or a local, certain bar experiences are available that you absolutely have to check off your Chicago “bar bucket list”. Here are some of the quintessential Chicago bar experiences as well as some of the best bars in the city you can make them happen.

Have an Old Style in a dive bar

One of the best ways to truly experience the bar culture of a particular city is to find a dive bar where you can swig down a few of the area’s favorite local light lager. In Chicago, that beer is Old Style and the dive bars in which to enjoy one in are plentiful.

Chicago’s dive bars run the gamut from the old – Nisei Lounge in Wrigleyville – to the new – Weegee’s Lounge in Logan Square – and everything in between. The Windy City is home to some truly special dive bars.

A Second City improv troupe favorite, Old Town Ale House, is where you can imagine John Belushi or Chris Farley sipping an Old Style. To experience the true dive vibe, though, you can’t miss the allegedly haunted Simon’s Tavern in Andersonville or a place dubbed “The Creepiest Bar in America”, L&L Tavern in Lakeview. What makes it so creepy? You can start with the fact that it was a favorite watering hole of multiple infamous serial killers and go from there.  

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Waste an afternoon in a tiki bar

Chicago reportedly isn’t called the Windy City because of the weather but it is an apt description nonetheless. The winters can be very cold and very windy and, even though the summer can produce absolutely beautiful days, Chicago will never be mistaken for a tropical climate. So it is that much more fun to find some of the wonderful and whimsical tiki bars around Chicago to kick back, sip a colorful drink with an umbrella and waste a Midwestern afternoon.

The most heralded bar in this category in Chicago is a speakeasy tiki bar in River North called Three Dots and a Dash. This secret tropical hideaway is a true Chicago gem and a must-visit for anyone serious about cocktails. It’s not the only tiki game in town, though. Lost Lake in Logan Square is another popular tiki spot and Trader Todd’s perfectly combines the tiki, karaoke and dive bar genres.

Check out the view from a rooftop bar

To really get a feel for the size and beauty of Chicago, you need to get a bird’s eye view. Luckily, Chicago has several great bar establishments perched high above the city where you can kick back after a long day, enjoy a drink, and look out over the city below.  

Chicago is home to more than a dozen rooftop bars and they all provide unique and memorable vantage points of the city. They are great to visit during the day when you can see Lake Michigan and the parks and beaches on its shores or at night when the lights of the city sparkle.

Cindy’s Rooftop at The Chicago Athletic Association Hotel and the I|O Lounge at The Godfrey Hotel Chicago are two of the best-known spots in the city. Raised is a hip and trendy urban rooftop bar and The Rooftop at Joe’s on Weed Street is a much more casual and laid back establishment. If you’re looking for a rooftop that suits you, Party Slate’s excellent list of rooftop bars is full of ideas.

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Pre-game in Wrigleyville 

Chicago is, above maybe anything else, a sports town. They love their Bears and their Blackhawks and their Bulls but there is no more iconic Chicago team than those lovable losers, the Chicago Cubs. The bars around their historic home, Wrigley Field, are an amazing mix of establishments where you have to have a few drinks before you kick back on the 100-plus-year-old seats and watch a ballgame.

Everyone has their own favorite pre-game haunt in Wrigleyville but a few bars stand above the rest. Although the number one spot of a top 10 list may go to different places, most can agree that bars like Cubby Bear, Sluggers, Casey Moran’s, G Man Tavern, and Murphy’s Bleachers must make the list.

Sip a drink on the banks of the Chicago River 

One of the most distinctive features of Chicago is the stunning and powerful river that runs through the middle of the city. There is not much that is better on a nice day than to sit on the Chicago Riverwalk and enjoy a beverage while taking in the sights and sounds. Most of the bars here close during the winter so enjoy them while you can.  

City Winery offers high-end food to go along with your lovely glass of wine and, if beer’s more your thing, you can check out Chicago Brewhouse where they specialize in locally brewed beers. The Northman Beer & Cider garden is a unique spot on the river. It brings the feel – and food – of a traditional European beer garden to the City of Big Shoulders.


Chicago has much to offer visitors and locals alike but the local bar scene in town is something special. We should all have a bar bucket list in our lives and, if you’re in the Windy City, that list should include dive bars, tiki bars, rooftop bars, baseball bars, and river bars. Each one of these experiences will give you an incredibly fun afternoon, evening, or late night and will certainly be something that you will remember for a long time.