One of the most interesting things about Chicago (and the Midwest in general) is tavern culture. Inherited from early German and Polish settlers to the New World, early American taverns had rooms for rent, an address for sending and receiving overseas mail, and most importantly a kitchen and bar area for serving food and drinks. During the height of saloon and tavern culture in 1910, the CHI had over 8,000 saloons; one for every 239 people.
Chicago’s food culture grew with these establishments; it was in Chicago taverns that ‘tavern-style pizza’ was popularized. It was where Polish immigrants popularized pierogies to a wider audience. Where ‘loaded’ and ‘stuffed’ hot dogs became popular. And where chopped Italian beef sandwiches became known in many parts of the Midwest as ‘tavern sandwiches.’
Unfortunately, Prohibition shut down a lot of bars; then the stockyards closed. The Daleys (as anti-alcohol mayors) made it harder to obtain or hold onto a liquor license. Recently, bars have had to deal with the dual threats of COVID and the rise of Internet culture! But luckily, saloons and taverns are now open all over the Chicagoland area…hopefully this time for good.
Chicago’s bar scene is nothing if varied. Here in this article, we’ll give you some recommendations for great Chicago bar experiences of all types; read on for more!
Three dots and three dashes mean ‘SOS’, the distress signal in Morse code! It’s a cheeky name for a bar that serves Polynesian boat drinks, but it could also represent the amount of liquor in many of their cocktails. Their large-sized drinks are meant to be shared, and they’ve got over 200 rum options on their list. A great place to go pretend it’s July and you’re on an island.
Cindy’s Rooftop
Okay, so if it’s actually sorta’ kinda’ warm…head over to Cindy’s. I mean, it is March. So it’s still quite literally freezing. But when the sun shines and we catch a couple of warm days; go for it. We’ve already seen guys in Wrigleyville in shorts, for what that’s worth. Even if it’s not warm, Cindy’s has great cocktails and an even better view of the marina on Lake Michigan. And for what it’s worth, the covered area at Cindy’s lets in a great view without the spring chills. A great place to pretend you’re in Miami and that you have a way cooler job than the one you currently work at.
Yep, it’s a whole subgenre of the bar in Chicago; the speakeasy. Remember, this was Capone’s town. Those big brass rails in old bars are even called ‘speakeasy rails,’ set up to keep the throng away from a bartenders’ workspace. Nowadays of course the speakeasy thing is to keep tourists and bros away…and maybe also to impart a bit of coolness to the establishment. This one’s an OG, and one of our favorites! Head a block down from the Milwaukee and Damen intersection, and look for a blank door lit by a single light bulb. Inside are some of the best Prohibition-era-style drinks in the neighborhood.
Clayton Hauck for Land and Sea Dept.
Well, we already mentioned Cindy’s, so it would be silly not to mention the Milk Room…especially now that the subject is ‘secret’ bars. A tongue-in-cheek reference to the room’s former function as an actual speakeasy, this spot might be one of the fanciest cocktail establishments in the entire country. Seriously. Bartenders serve up vintage spirits (at eye-popping prices!) to a candle-lit bar that only has eight seats. P.S.- If you like this type of thing, also check out Billy Sunday and the Office (the bar under the Aviary.)
This spot’s been open a couple of years, so it’s not exactly new. But it’s made more than a few ‘best bars in the world’ lists, so we had to include it! A mixture of a high-end Japanese restaurant and a cocktail bar, Kumiko is a great place for a romantic evening or a place to really make an impression. Noah Sandoval from Oriole is in charge of the food. (Yes, the two-Michelin-starred Oriole.) Speaking of food; if you want to eat in a more serious way, just head downstairs to Kikko, the bar’s basement dining room. This is a place that has to be seen to be believed; it needs to be experienced! As one might expect, reservations are required, sometimes weeks ahead of time. It’s worth it.
Yep, it’s all in the name. This is one of the best wine spots in the CHI. If you want to try some wild ‘natty wine,’ some new school Cali ‘garagiste’ reds, or some unknown Chardonnay, this is the place. It’s also a good place to go to if you don’t understand anything we said in the last sentence! Webster’s is cool but quite unpretentious, and they have some great value wine selections as well.
Almost didn’t want to write this one in here, as it’s already so crowded. But it’s just too cool not to mention. On paper, the Hideout isn’t much. It’s an old house that was turned into a bar in the middle of an industrial neighborhood. They have cheap beer, concerts, and one of Chicago’s best parties this side of Smart Bar. Go early, stay late.
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