The Best Cocktail Bars In Chicago

Unlike some glitzier spots on this guide, Kumiko doesn’t have velvet curtains or decorations that should have “do not touch” signs. Instead, this upscale West Loop cocktail bar is more nuanced and relaxed, opting for an intimate, pristine space. This means it’s ideal for anniversary drinks, or quieter celebrations with people who have energy levels that are a six out of ten. The calm way the staff describes flavor profiles is soothing, and the menus look like artfully crafted zines. This attention to detail extends to their food and drink, with creative cocktails like a bold-yet-light Old Fashioned with green tea, and a crispy tonkatsu sando with pillowy milk bread.

For Chicago, The Aviary in the West Loop is the special occasion cocktail bar. Which isn’t surprising since it’s from the Alinea group—so expect elaborate, Alinea-esque drinks on the menu here. Cocktails start around $27, and vary in the amount they look like science experiments. For example, The Jungle Bird has little clear tapioca-like balls filled with rum that pop in your mouth, and the In The Rocks goes even further—it comes in a ball of ice you need to snap with a rubber band. You can make reservations, but you can also walk in (there might be a wait, but that will give you some time to quickly reread your eighth-grade science textbook). Plus their basement speakeasy, The Office, is also great if you want to keep things going afterwards.

The Violet Hour in Wicker Park is a good destination cocktail bar from the people who own Avec and The Publican. This place might seem like it’s trying hard to be cool—from the unmarked door to the “House Rules” (which ban baseball caps, Cosmopolitans, and any drink that’s a -bomb, jager or otherwise). It doesn’t come off as obnoxious, though, because the craft cocktails really are good. Inside, it feels like a lounge more than a bar—it’s dark, with lots of candlelight, plus comfy chairs and tables that can be sectioned off for privacy. Overall, not a bad spot to celebrate the launch of your top-secret baseball-cap-recycling startup.

The Alderman is not a great place to voice your zoning complaints (though perhaps the nice bartender would be open to that conversation), but you can get great cocktails. Located behind an easily locatable door in Pilsen Yards, it may not be particularly hidden but it still carries the spirit of a speakeasy. It’s dark and intimate with only 16 seats, and though you can walk in, we recommend placing a reservation. All of the drinks are fantastic, with a rotating selection of cocktails like the Sichuan Panda made with baijiu, sesame oil, and peppercorn, or the Blind Luck with gin and chai vermouth.

Though Osito’s Tap technically isn't a speakeasy, it’s fun to treat this Little Village bar like one. Do this by walking through its second, “secret” entrance—just past the booze-stocked aisles of Moreno's, the attached liquor store. At Osito’s Tap, its rustic brick space is overflowing with camaraderie. Friends cram into leather booths, regulars post up at their “assigned” bar seats, and there’s usually a large group taking advantage of Happy Hour. The cocktails are fantastic, from classic margaritas to originals like El Oscuro: a smoky Old Fashioned with orange and chocolate bitters, and an ancho chile reduction. And their short food menu also has tasty Mexican dishes like mushroom-stuffed molotes.

During Parachute’s 10-year lifespan, it has evolved from two different Korean restaurant concepts into its current form: a full-fledged vinyl listening bar. Now called Parachute HiFi, this basement-esque Avondale spot with Hank Williams staples and Korean oldies crackling through the speakers is a great hang, especially with their creative food-inspired cocktails. A prosciutto-washed gin drink deftly balances meaty and fruity flavors, while spoonfuls of the bingsu’s Fruity Pebbles and shaved makgeolli ice (yes, this cocktail is eaten) make for a perfect boozy dessert. It can get busy even on a Wednesday with couples and friends snacking on bordelaise-dipped burgers or rice cake pad thai, so tell your fellow audiophiles to meet you there early.

Best Intentions ended its three-year hiatus quietly, simply writing “we back” on a teeny note posted outside their building. And this Logan Square dive bar reopened in full force (and hopefully they never leave us again). No barstool stays empty for long, and the space is filled with people happy to stand while funk and soul music blasts through the speakers. Unlike most dives, the cocktails are fantastic but still keep the dive bar price point (around $10). Plus, they have a great patio and their $6 smashburger is the ideal bar snack—you can even order a baker’s dozen for $72.

Despite opening in 2021, this Andersonville bar feels like a neighborhood staple that’s been around since the Daley era (specifically Daley Senior). It’s welcoming and lively, with disco lights and a playlist full of jams like No Diggity—all of which make it a fun place. There aren’t gimmicky ingredients, but their elevated takes on classics, like an Old Fashioned with ginger maple syrup, will make you wish that was the local standard. And their quiet sidewalk patio (often full of people with their dogs) is ideal for a chiller vibe.

They have drinks with names like the Victorian, vintage liqueurs, and price tags hovering around $30. It’s the kind of place you take a first date to impress them with your “I just Googled this” knowledge of rare amaro. The intimate space only has a few tables (ideal for quiet conversations under the crystal chandeliers), but they also have group-friendly seating on their sidewalk patio.

Nine Bar is special. Not only because it was the first cocktail bar in Chinatown, but  because this speakeasy (hidden behind Moon Palace Express’ “kitchen door”) has fantastic Asian-inspired cocktails and delicious food. The dark space is cozy, with Tron-esque neon lights. Both the drink and food menus are short but full of hits, with things like a smoky rye cocktail with Chinese five spice and the crispy mapo hot fries. Weeknights are more low-key, perfect for a relaxed hang at the bar or on one of their comfy couches. But for a more hyped atmosphere, come by during a weekend DJ set.

This River North spot is a tiki bar serving tropical cocktails in mugs shaped like pineapples, conch shells, and mermaids, among other things. It’s a good place to go before your Super-Bowl-winning trip to Disneyland, because your (very generous) friends can buy you the $425 “Treasure Chest,” a cocktail for 6-8 people. It gets especially crowded on weekends, so unless you want to be standing and getting an unintentional arm workout by holding up that chest full of booze, book a table in advance.

Milk Room is a speakeasy-esque bar in a hallway of the Chicago Athletic Association Hotel. And this place is tiny, with only an intimate eight-seat bar. So since space is limited, we highly recommend booking a reservation (each seating also comes with a time limit ranging between one to two hours). The cocktails often involve some very rare scotches, whiskies, and other spirits, and each feels like a small investment ($24-$75). Their expert bartender will help you find the ideal cocktail based on your preferences—unless, of course, your preference is cheap bottom-shelf stuff.

Regardless of the liquor or bitters, perhaps the best ingredient for the optimal cocktail experience is live music. And with a robust drink menu of 52 cocktails, along with regularly scheduled acts, Lazy Bird in the West Loop makes a solid argument for this. This dimly lit, 1940s-meets-modernist bar is hidden in the basement of the Hoxton, and has plenty of soft couches and chairs that you wish existed in your apartment. Performances range from solo jazz piano to more upbeat DJ sets so check their performance calendar first.

This Logan Square spot feels like a secret clubhouse. Located on a quiet side street with only a discreet bird silhouette sign, Meadowlark is easy to miss. But once inside, you’ll find a dark wooden space, comfy leather couches, and some great small plates and drinks—which isn’t a big surprise since this comes from the team behind Union and Lardon. And to keep things from getting stale, the drink and food menu rotates and always has a theme, like “Birds of the Midwest” or “Chicago World’s Fair.”

Victor Bar reminds us of a speakeasy minus a secret entrance that you’ll probably overlook at least six times. And this narrow North Center spot is brooding yet charming—candlelight, a friendly crowd, and you'll never need to worry about losing your voice while trying to have a conversation. It's perfect for sitting with a friend, swirling around a well-balanced sazerac and posing very serious questions about societal collapse, existential crises, and how many chicken nuggets is too many.

Just above Logan Square bar, Slippery Slope, is its chiller, retro-themed cocktail spot, The Heavy Feather. And unlike its downstairs sibling, Heavy Feather has plenty of standing tables, leather booths, and comfy 70’s-esque leather rolly chairs. All of the cocktails here are great—from classic espresso martinis and mezcal Old Fashioneds, to a grasshopper that’s everything you want in a boozy milkshake. They don’t serve food, but midnight appearances from a guy selling tamales might be in the cards.

Scofflaw’s fireplaces (yes they have two) and living room-esque design is perfect if you don't want to stay home and drink in your living room, but still want to feel like you’re in one. The cocktail list rotates every three months, with a particular focus on gin, like the flowery and herbaceous Heliotrope with gin, lavender, rosemary, and arak. The food menu has an eclectic mix of dishes like pea curry dip and Korean rice cakes, but the cheesy smashburger is the best thing here. Plus, they have free freshly-baked chocolate chip cookies after midnight.

Sparrow has an impressive collection of rum from 22 different countries, so it’s no surprise that most of the drinks here use it as a base. Though the cocktail menu is short, it’s wide-ranging—from sweet and refreshing drinks like the fruity Floridita with grapefruit and lime to a very strong Á La Louisiane with rye, rum, and absinthe. The narrow space is charming, with Art Deco design and vintage touches like a phone booth and room numbers on the bathrooms to make them look like apartments (this was originally a lobby bar during the 1920’s after all). And though the bartenders may be decked out in button-ups and ties, it’s refined without feeling stuffy.

Moonflower is a dimly lit, spacious Portage Park bar that’s ideal for a low-key group hang or date. The cocktail menu has a mix of solid classics like Old Fashioneds and negronis, but the draw is the more unique drinks like a mezcal and tequila cocktail that's mixed with Milkis. They have snacks like monthly-rotating deviled eggs and hot dogs from their resident pop-up, Funeral Potatoes. The plant-filled space has a great funky soundtrack, but the music is never too loud that you’ll have to resort to texting the person sitting next to you. Plus, Moonflower is actually a great bar twofer, since they also have a more intimate basement bar, Nightshade, with its own creative drink menu.

Look closely at the stretch of Kedzie in Albany Park full of taquerias and Persian restaurants and you’ll find this tiny bar. Inside, Bokeh’s space is incredibly narrow, with just a handful of tables for two and bar seating—which lends itself to a relaxing solo venture (post kabobs or tacos, preferably) or a date night (also after kabobs or tacos). The long cocktail menu has a nice balance of classics and creative originals, like a not-too-sweet umami-tinged banana peel and miso old fashioned. And though indoor seating is limited, they do have a few sidewalk picnic tables outside.