16 Oldest Bars and Restaurants in Chicago
Est. 1885 | 1758 North Sedgwick Street
Located in the Old Town Triangle, this place was once a real-deal speakeasy, back when alcohol was a no-no. It had all the musts – a secret entrance, an antique wooden bar that still stands to this today, and gin a-brewin’ in a bathtub upstairs. Now, it’s your classic (and totally legit) neighborhood joint serving good drinks and tavern eats.
Est. 1897 | 832 North Greenview Avenue
Another neighborhood bar serving cheap drinks, this Noble Square establishment may have operated as a speakeasy at some point too, but the details are a bit blurry. Once you walk in, take in the vibe, and see all the vintage furnishings, it’s hard not to imagine this place having a colorful past.
Est. 1898 | 17 West Adams Street
Founded by a German immigrant who sold beer in Chicago at the 1893 World’s Fair, this family-owned business has come a Chicago legend. Unlike more rebellious establishments, they kept things kosher during Prohibition by stepping up their food game and offering non-alcoholic beer, until of course, they became the very first place to obtain a liquor license after the ban was lifted. ‘Know what else is crazy? They only served alcohol to men (ouch), that is, until 1969 when Gloria Steinem protested for women’s rights. ‘Cause ladies like a cold one too. (Thanks, sister).
Est. 1905 | 111 North State Street
Perched atop the Macy’s flagship on State is The Walnut Room – the “first-ever restaurant to open inside a department store.” Just take a look around – sophisticated and classy is what this place is all about. Plus, if you’re planning on taking a day to shop, this is the perfect place to “drop,” if you will.
Est. 1909 | 1531 West Taylor Street
There’s something about Italian food that it just seems to taste better if it’s made with generations of family tradition behind it. An absolute staple in the Taylor Street area of Little Italy, it’s a true veteran of Chicago restaurants, and the food will having you coming back for more, guaranteed.
Est. 1921 | 678 North Orleans Street
Built shortly after the Fire, one of the city’s most well-known, long-standing establishments was one of the only wooden buildings left after a law was passed to prohibit them. The name comes from its green door – a secret code that served as a beacon for anyone trying to get some of that giggle water. Today, it has a modern speakeasy downstairs called Drifter, where you can experience what it may have been like to come here in the ’20s.
Est. 1923 | 565 West Jackson Boulevard
The level of hospitality provided at this place rivals none, and anyone who’s been there can attest! The second you walk in, you’ll feel like you’re dining with family, and it’s been that way for decades. This breakfast diner is known throughout the world, having been visited by politicians, celebrities and athletes alike.
Est. 1927 | 71 West Monroe Street
Treat yourself to not one – but three restaurants in a single, historic location. This family business has worked for decades upon decades to provide top-notch, regional Italian eats, and has one of the most impressive collections of wine in the city to back it up. Although it dates back to the ’20s, step inside this vibrantly decorated space and it’ll instantly feel timeless.
Est. 1929 | 1220 North State Parkway
This piano bar in the Gold Coast proudly totes the third oldest liquor license in the city. Discreetly located underneath the Canterbury Courts apartments, this is the place to go when you want to sing the night away. Having been frequented by a variety of personalities and iconic names throughout its history, visiting here will make you feel apart of something larger than life.
Est. 1932 | 1942 West Irving Park Road
Serving up traditional Chinese eats to hungry locals since the ’30s, this place has never left its spot in Irving Park. So they must be doing something right. Don’t be fooled by its somewhat nondescript appearance. This place dishes out massive portions, so be sure to come with an appetite.
Est. 1932 | 1655 North Sedgwick Street
When Frank Sinatra is one of your regulars, you know you’ve made history. The impact this place has on Chicago history speaks for itself – just browse through their collection of memories submitted to their website by nostalgic patrons. According to them, the building itself was formerly owned by Schlitz during the first World War. And (of course) it operated for a while as a speakeasy. So yeah, they’ve seen it all.
Est. 1933 | 724 West Wrightwood Avenue
Named after the corner of Burling and Wrightwood where it stands, this Lincoln Park dive is beloved by the neighborhood. Owned by the same family for three generations, it began as a totally innocent (ahem) “soda shop” during the tail end of the nation’s dry years. After the ban ended, it was in the group of the first Chicago establishments to receive a liquor license. So, as you can imagine, it was probably pretty rowdy back then. And it’s still known for getting pretty rowdy now.
Est. 1933 | 140 East Walton Place
Located in The Drake Hotel, a Chicago landmark, this place is the definition of old time-y elegance. The intimate lounge wouldn’t be slinging the delicious cocktails they are today without becoming the second place in the city to obtain a liquor license after Prohibition. If you’re looking for a place where you’ll feel completely transported in time, this is it.
Est. 1934 | 5210 North Clark Street
Brought to life by a Swedish immigrant, this bar is one of the focal points of Andersonville’s deeply rooted culture. Complete with nautical fixtures and Viking memorabilia, come here to sample a great variety of Swedish beers or to take a warm sip of glögg, a Swedish mulled wine.
Est. 1938 | 3758 South Union Avenue
South Side pride runs deep here, given this Irish pub has been serving beer to the neighborhood since the late ’30s. As many others on this list, it’s been run by the same family for three generations. If you’re a White Sox fan, you’ll feel right at home here.
Est. 1946 | 425 West Armitage Avenue
Although it’s the youngest on this list, this Irish pub in Lincoln Park has still had a pretty impressive lifespan, having been around since the late ’40s. It’s easily one of the most laid-back, inviting places in the area – somewhere you’ll always feel welcome. And so will your furry friend, for that matter, since it’s a dog-friendly bar.
Featured Image: Coq d’Or vintage postcard