As Al Capone’s favorite haunt in the 1920s, Green Mill is a jazz bar that makes you feel like you’re re-living history. The cocktails offered here are mostly the classics. The entertainment schedule changes frequently, so be sure to check it out beforehand.
The Green Mill Cocktail Lounge, 4802 N Broadway St Chicago, IL 60640 773-878-5552
An old upright piano helps give this venue a speakeasy vibe, and the cocktails served are sublime. At this vintage-looking two-story cocktail house, you’ll be able to appreciate the classics of cocktail-making and a true 1930s atmosphere. Perfect for sharing are the punch bowls, especially the Golden Fleece, with pineapple syrup, green tea and gin.
Barrelhouse Flat, 2625 N Lincoln Ave Chicago, IL 60647 773-857-0421
Scofflaw is a gin-focused bar that shows off the ingredient’s versatile attributes in its cocktails. The small bar is packed with Victorian antique fixtures and old, leather couches. They also have an arsenal of absinthe, tequila and whiskey, and on weekends they serve a burger-based brunch.
Scofflaw, 3201 W Armitage Ave Chicago, IL 60647 773-252-9700
Named after a T.S. Eliot poem, the bar is a flirty concoction of luxe ingredients and 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 they don’t take reservations, so either go on a weekday or show up early on weekends. They also have a list of house rules which includes no cell phones and no standing room, so you know it’s good for a conversational and intimate evening.
The Violet Hour 1520 N Damen Ave Chicago, IL 60622 773-252-1500
Located in River North, award-winning drinks from a veteran of Violet Hour, Mike Ryan, have made this a go-to destination. The drinks list features a mix of spicy, sweet and traditional cocktails with a twist, and the large 40-foot bar in the front is stocked with most liquors. Be sure to try the War of the Roses cocktail, made with Pimm’s and Chase elderflower.
Sable Kitchen & Bar, 505 N. State St Chicago, IL 60654 312-755-9704
The Aviary serves what many have described as mind-blowing, beautiful creations. The bartenders here are trained like chefs, focusing on concocting unique blends, and the bar looks like a swanky lounge, with its elaborate decor and booths.
The Aviary, 955 W Fulton Market Chicago, IL 60607 312-226-0868
The menu here is always changing, and all the cocktails are handcrafted, as are the booze sodas. The bartenders here have penchants for using unusual ingredients, like syrup with maidenhair ferns. However, the cocktails themselves are a nod to tradition mixed with tastes you won’t find anywhere else.
Billy Sunday, 3141 W Logan Blvd Chicago, IL 60647 773-661-2485
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, absinthe and spices available. Delectable bar food is also a highlight of this establishment, especially the spicy-sweet Thai fried chicken.
Three Dots and A Dash, 435 N Clark St Chicago, IL 60654 (located on Hubbard St) 312-610-4220