10 Historic Bars in Chicago

It was in 1827 that John Kinzie opened Chicago’s first tavern at Wolf’s Point in what is now the Loop. It was known for its strong homemade whiskey and for serving as a central hub for commerce, politicking, and land deals. That tavern is now long gone but Chicago’s love affair with its bars has hardly subsided.  


Chicago’s bars have served many purposes over the decades: showcases for the city’s diverse talents, speakeasies during the dark days of prohibition, and community centers for an incredibly diverse set of newly arrived immigrants. This list of 10 bars is by no means comprehensive but instead represents a good cross-section of taverns in the city that embrace and preserve their history.  

Laschet’s Inn - North Center 

First opened in 1971, this bierstube catered to the large population of German-Americans centered around North Center and Lincoln Square. Up the stairs and through the swinging doors you’ll find enormous steins of German lagers, typically hearty German food, and plenty of German-speakers enjoying stammtisch with their friends.

The walls are covered in photos of past princes and princesses crowned by Rheinischer Verein, a German Mardi Gras organization founded in Chicago way back in 1890.

Goose Island Brewery - Ranch Triangle

As of 2018, Chicago has more breweries than any other U.S. city with 167 within city limits. Prohibition wiped out most of the city’s early breweries, but in 1988 two aspiring brewers took a gamble and opened Goose Island in this Lincoln Park-adjacent location. The brewery has expanded substantially since its humble start and is, arguably, the genesis of the Chicago craft-brewing revolution.

The Billy Goat - Streeterville

This storied tavern, long-popular with journalists and comedians, is perhaps best-known for its appearance in a famous early SNL sketch (“Cheezborger!”). Owner Sam Sianis is also the origin of the notorious Billy Goat curse that many say denied the Cubs a World Series appearance for nearly a century.

The tavern itself is something of a museum of Chicago history, featuring hundreds of smoke-stained photos and clippings documenting decades of Chicago writers, cultural figures, and politicians.

Rainbo Club - Ukrainian Village

Division Street, once known as The Polish Broadway, was once home to dozens of bars showcasing the talents of the likes of polka legend “Li’l Wally” Jagiello. The clamshell stage at the Rainbo Club has hosted everything from burlesque to jazz in the past, and later played an important role in Chicago’s alternative music scene in the 1990s.

The bar made an appearance in High Fidelity and featured prominently in the music video for poet and songwriter David Berman’s “Random Rules.”

Woodlawn Tap - Hyde Park 

Long a laid-back fixture on the northwest corner of the University of Chicago’s campus, Woodlawn Tap is known for providing cheap drinks and food to students. This bar is better known as Jimmy’s after its iconic proprietor Jimmy Wilson, who was beloved by the neighborhood and generations of students and faculty—so much so that he was honored with an honorary doctorate from the university.

Just don’t ask for a Budweiser—despite even the appeals of Harry Carry, Jimmy’s hasn’t carried it for decades due to a pricing dispute dating back well over half a century.

Shinnick’s Pub - Bridgeport

The pub at 38th and Union first opened its doors in the 1890s, serving the neighborhood’s large Irish immigrant community. Like many a classic Chicago tavern, they didn’t let Prohibition impede their operations and the pub became known as Shinnick’s in 1934.

The bar was popular with the neighborhood’s large contingent of machine politicians in the 20th century, with its backroom often described as “Little City Hall.” Looking around the place in 2019, it is decidedly less smoke-filled but, other than that, little has changed at this legendary south-side spot.

Simon’s - Andersonville

Simon’s, with its ocean liner-inspired decor, was one of the first bars to get a liquor license after the repeal of Prohibition in 1934 but, as the stories go, it wasn’t exactly difficult to a drink there before that.

As with many of the taverns on this list, it catered to its neighborhood’s immigrants, in this case, the large contingent of Swedish people that populated the north side. Today patrons enjoy live music and reasonably priced drinks, including its famous Swedish glogg. This spiced wine concoction is cooked up in giant batches and served hot during the winter and is even available as a slushy during the summer.

Old Town Ale House - Old Town

The Ale House is one of the last remnants of Old Town’s grittier past. Its patrons over the years are a “who’s who” of Chicago cultural icons, including the likes of Second City legends Bill Murray, Stephen Colbert, and John Belushi.

This tavern is somewhat infamously bedecked with bawdy paintings of politicians that are best not described in great detail on a family-friendly blog. Look carefully among these often lewd paintings for a loving depiction of long-time patrons Chaz and Roger Ebert, the latter of whom described the Old Town Ale House as “the best bar in the world that I know about".

Sidetrack - Boystown

The history of LGBTQ-friendly bars in Chicago is fraught with political, legal, and cultural challenges. Police raids and political harassment made it difficult to operate a bar open to all until the latter part of the 20th century.

Sidetrack was opened in 1982 as a modest tavern without a sign where patrons used beer crates as barstools. It is now a sleek and welcoming multiroom complex in booming Boystown that serves as a cultural center for Chicago’s LGBTQ community.

The Green Mill Cocktail Lounge - Uptown

Perhaps the most legendary of them all, The Green Mill’s gaudy lighted exterior announces its rich history to all that pass by. It first opened in 1907 as a hotspot for silent film stars and, like many bars on this list, was largely unaffected by Prohibition when some of Chicago’s most ignominious gangsters called it home.

Too many entertainers to list passed through its doors during its heyday in the 1940s. The bar is experiencing a renaissance now, with live music and poetry readings just about any night of the week.

BONUS: Hala Kahiki - River Grove

Rose and Stanley Sacharski, perhaps looking to move into a more cheery line of work than the funeral home they operated, established this Polynesian hideaway in the suburbs during the height of the tiki craze in 1964.

Its appeal today lies in the fact that, except for a few expansions, it is virtually unchanged in appearance since that time. The over-the-top decor and seriously boozy drinks are something of a time-capsule. It stands today as one of the few remaining classic tiki bars in the U.S.