Prohibition, which banned the sale of alcohol throughout the United States from 1920 until 1933, shaped the country irrevocably – but it was arguably the city of Chicago, with its mobster network and deeply ingrained drinking culture, which was hit the hardest. Since then, The Windy City has truly risen from the proverbial ashes, not least in terms of its vibrant landscape of cocktail lounges and jazz bars, speakeasies and pubs, sports bars and hotel rooftops. But to really appreciate the Second City’s journey from bathtub gin and bootleg booze to the glittering present, you’ll need to hit up the best cocktail bars in Chicago.
As Al Capone’s favorite haunt in the 1920s, the Green Mill is a jazz bar that makes you feel like you’re reliving history. The cocktails offered here are mostly the classics; order one and sit back to enjoy the live music. The entertainment schedule changes frequently, so be sure to check out their website in advance to see what’s in store.
Named after a TS Eliot poem, the bar is a flirty concoction of luxe ingredients and sleek decor. The main entrance is hidden by a street art facade, but inside, you’ll be transported into a room with rich drapes and imposing blue-backed chairs. In the heart of Wicker Park, this bar gets packed quickly and doesn’t take reservations, so either go on a weekday or show up early if you’re planning to stop by on a weekend. It also has a list of house rules that includes no cell phones and no standing room, so you know it’s good for a conversational and intimate evening.
Scofflaw is a bar that aims to show off the versatility of the ingredients used in its cocktails, especially those with gin, while the small bar is packed with antique Victorian fixtures and old leather couches. They also have an arsenal of absinthe, tequila and whiskey, and on weekends they serve a burger-based brunch.
The Aviary serves what many have described as ‘mind-blowing’ creations. The bartenders here are trained like chefs, focusing on concocting unique blends, and the bar has the ambience of a swanky lounge, with elaborate decor and comfortable booths.
Award-winning drinks from a veteran of The Violet Hour, Mike Ryan, have made Sable Kitchen & Bar a go-to destination. Located in River North, the drinks list features a mix of spicy, sweet and traditional cocktails with a twist, while the 40-foot bar in front is stocked with most liquors. Be sure to try the War of the Roses cocktail, made with Pimm’s and Chase elderflower liqueur.
The menu here is always changing, and all the cocktails are handcrafted, as are the boozy sodas. The bartenders have a penchant for using unusual ingredients, like syrup with maidenhair ferns, while the cocktails themselves are a nod to tradition mixed with tastes you won’t find anywhere else.
Opened in 2013, this tiki bar helped set off the trend of tiki-themed drinks in Chicago. The bar serves aesthetically pleasing cocktails, garnished with pansies and orchids in skull, coconut and tiki-head glasses. There are more than 165 rums, absinthes and spices available, plus a good range of delectable bar food, with the spicy-sweet Thai fried chicken a common favorite.