Where to Drink Now in Chicago

Chicago doesn’t tend to shout about its cocktail bars. It doesn’t need to. A city with Julia Momosé behind one bar and Grant Achatz dreaming up what happens at another has quietly become one of the most rewarding places in America to spend an evening with a very good drink, and its rooms are earning international attention to match.

The cocktail scene here has range. A night out might involve Japanese whisky and an exquisitely considered menu, a vintage spirit you’re unlikely to encounter again, or a martini served in a room that makes you wish you’d worn the better dress. The neighborhood taverns are equally capable of holding your attention. Some now have international rankings to go with their regulars.

Seven Chicago bars made North America’s 50 Best Bars’ top 100 in 2026, with Kumiko also appearing on the global extended list. Meanwhile, newer arrivals are bringing tableside cocktail service, playful menus, and a healthy amount of velvet into the equation. Between the established heavyweights and the rooms making a name for themselves, Chicago gives you plenty of reasons to stay for another. These are the 20 worth knowing, and you will need more than one night.

Kumiko

Julia Momosé understands something that can get lost when cocktails become competitive sport: the person drinking one matters. At her Japanese dining bar, the attention extends from the ingredients to the way an evening is paced, with food, drinks, and hospitality all getting their due. Kumiko’s 2026 Michter’s Art of Hospitality Award from North America’s 50 Best Bars feels particularly fitting.

Ranked No. 11 in North America and No. 70 globally, the West Loop destination brings Japanese and American influences together through seasonal cocktails, sake, shochu, and Japanese whisky. Momosé’s work invites exploration without making the experience feel like homework. For anyone who travels for a great bar—and I consider that an entirely legitimate reason to book a flight—Kumiko belongs near the top of the Chicago list.

The Aviary

Grant Achatz was never likely to open a bar where the most interesting thing happening was the garnish. At The Aviary, the imagination associated with his culinary world extends to everything from ice and temperature to aroma, texture, and the way a drink is presented. A cocktail here can command the table’s attention before anyone has taken a sip.

The options reflect that ambition: a three-course cocktail progression, a seasonal five-course food-and-cocktail menu, or a seven-course Kitchen Table experience seated inside the bar’s “bird cage,” with a view of the work in progress. Limited à la carte reservations are available, too. This is an evening to plan around, particularly if your dinner companion has a habit of declaring that they’ve seen it all.

After

Curtis Duffy and Ryan Chetiyawardana make an intriguing pairing. At After, the chef behind Ever has partnered with Chetiyawardana’s Mr Lyan Studio, bringing two substantial creative reputations to the same cocktail lounge.

Seasonal drinks, culinary technique, and food from Duffy’s world give the Fulton Market address plenty of substance. The partnership adds a fresh reason to pay attention, particularly for anyone familiar with Mr Lyan’s influence on contemporary cocktail culture. After offers the opportunity to explore that work alongside Duffy’s approach to flavor and hospitality. It also makes an excellent argument for giving the bar portion of the evening as much consideration as dinner.

Meadowlark

Meadowlark gives you a reason to actually read the cocktail menu. The 30-seat Logan Square hideaway, hidden behind an unmarked door, builds its collections around ideas that extend well beyond a catchy drink name.

Its “Composition Book” menu explored childhood memories through cocktails including Recess, Field Trip, and Summer Camp, presented in a notebook-style format with activities for guests. Behind the nostalgia is the technical work of Abe Vucekovich and the bar team, who give the playful premise some serious substance. Ranked No. 65 on North America’s 50 Best Bars 2026, Meadowlark offers the pleasure of discovering what a familiar memory might taste like in entirely unfamiliar hands. This version of recess comes with a better drinks selection.

Photo Credit: The Aviary/The Office

The Office

The Office is the sort of place that could substantially improve your attitude toward working late. Beneath The Aviary, behind an unmarked door, the 21-seat speakeasy turns its attention to classic cocktails, vintage spirits, and luxury bites.

The draw is the chance to explore exceptional bottles in an intimate setting, with a bartender who can help you figure out which ones deserve your attention. Vintage spirits give familiar cocktails an added dimension: the recipe may be recognizable, while what’s inside the bottle has its own history. For collectors and curious drinkers alike, that is a compelling way to spend an evening—and a much better conversation starter than your actual office.

Gus’ Sip & Dip

A Breakfast Martini with honey toast for dipping is a fairly persuasive introduction. Gus’ Sip & Dip has plenty more where that came from, with a 30-cocktail menu that gives familiar orders the benefit of Kevin Beary’s considerable expertise.

Opened in late 2024 and ranked No. 27 on North America’s 50 Best Bars in 2026, the River North tavern has oak-paneled walls, leather booths, and bartenders in white jackets. The drinks have included a Wisconsin Old Fashioned, Sazerac, and a Grasshopper crowned with shaved ice. As for the “dip” part of the equation, the crab Rangoon version arrives with wonton crisps. Cocktails and a substantial snack are a pairing I’m always happy to support.

Nine Bar

The kitchen door at Moon Palace Express leads to an excellent reason to extend your evening in Chinatown. Nine Bar draws from an ingredient list that includes hojicha, pandan, Sichuan peppercorn, and goji berry sake, making the menu particularly rewarding for anyone willing to stray from their standard order.

The Paper Dragon brings tequila, passion fruit, citrus, and Sichuan peppercorn together; Cheating Death combines rye, rhubarb amaro, Chinese five spice, and umami bitters. The drinks have a clear connection to the bar’s Asian influences, with enough variety to make choosing the next one interesting. Ranked No. 76 on North America’s 50 Best Bars 2026, Nine Bar gives its hidden entrance something worthwhile to conceal.

Queen Mary Tavern

Queen Mary takes its drinking inspiration from the sea, a promising starting point given the historical enthusiasm sailors had for a strong pour. The Wicker Park tavern celebrates maritime spirits and drinking culture, with a particular interest in gin, rum, Scotch, sherry, and Madeira.

Named for former proprietor Maria Kafka, the bar opened in its current incarnation in 2015 and has since earned a place on 50 Best Discovery as well as No. 80 on North America’s 50 Best Bars 2026. Its focus gives spirit enthusiasts plenty to explore while preserving the appeal of a neighborhood tavern. The nautical influence is in the bottles as much as the atmosphere, which is exactly where it should be.

Three Dots And A Dash

When Chicago’s temperature starts behaving badly, a subterranean tropical bar has obvious advantages. Three Dots and a Dash delivers a full change of scenery: exuberant décor, elaborate cocktail vessels, fresh fruit, cold-pressed juices, and enough rum to make the weather briefly irrelevant.

The River North destination, included in 50 Best Discovery, puts considerable research behind the fun. Its namesake cocktail brings together aged Martinique rhum agricole and Guyana rum with lime, orange, falernum, and allspice. Large-format drinks make the experience particularly suited to a group, although choosing your drinking companions wisely remains your responsibility. A shared tropical cocktail is a commitment.

The Bamboo Room

The Bamboo Room deserves its own entry, even though you’ll find it inside Three Dots and a Dash. The dedicated rum bar offers a more focused exploration of the spirit, including rhum agricole, through refined cocktails in several styles.

For anyone whose interest in rum extends to where it comes from and how it’s made, the appeal is obvious. A dedicated menu, rum flights, and opportunities to explore distinctive bottles make this a different experience from the larger tropical bar around it. Both have their place in a Chicago night out. The Bamboo Room is the one to book when you want to spend a little more time considering what’s in your glass.

Sparrow

A 1927 Art Deco building makes a lovely home for a rum bar. Sparrow takes full advantage of its Gold Coast address, reimagining the lobby bar that once occupied the space with a drinks program centered on Cuban classics and Caribbean-inspired creations.

Included in 50 Best Discovery, it has the romance of an earlier era and a rum selection that gives the cocktail menu depth. A daiquiri makes an appropriate introduction; the wider collection offers plenty of reasons to continue exploring. There’s no food and no reservations, which makes the evening’s logistics refreshingly straightforward: eat something, turn up, and see where a good rum drink takes you.

Billy Sunday

Billy Sunday is a dangerous place for anyone who says they’ll just have a quick digestif. The Logan Square cocktail parlour keeps hundreds of bottles of amaro, including vintages spanning the last century. A glance through the spirits book could easily become the evening’s main activity.

Recognized by 50 Best Discovery, the bar folds that collection into drinks such as the Vintage Amaro Daiquiri, while seasonal cocktails and spirits flights offer other ways to explore. The Victorian, combining genever, alpine amaro, Fernet, sirop de capillaire, and wormwood bitters, gives a sense of the interests at play. A bartender’s guidance is useful here. So is accepting that your quick drink may require a little longer.

Photo Credit: Bisous Chicago

Bisous

Bisous had me at Parisian romance and martinis. The Fulton Market bar takes its cues from 1960s Paris, with velvet booths, patterned wallpaper, warm globe lighting, and a substantial marble bar. It’s an appealing setting for a date, especially one with someone who understands that cocktails warrant a reservation of their own.

Ranked No. 30 on North America’s 50 Best Bars 2026, the bar gives the martini’s extended family plenty of attention, including the Alaska, Gibson, Martinez, and Vesper. The savory Olivette combines olive leaf-infused gin, vermouth, and saline, while the food has included caviar and chips, rillettes, and premium tinned fish. A French-inspired room with strong drinks and something salty to nibble on: sometimes the formula is already quite good.

Lemon

Lemon understands the appeal of a night that has somewhere to go after the first round. The West Town cocktail bar doubles as a performance venue, pairing its drinks with live entertainment in a room furnished with purple curtains, leather chairs, and candlelight.

The combination earned North America’s Campari One to Watch Award in 2025, giving the bar a substantial endorsement early in its story. Its appeal lies in the possibility of making an evening of both the program onstage and the one behind the bar. Check the calendar before booking the rest of your night. This is the kind of place that could make those later plans feel unnecessary.

Kitty’s Cosmopolitan Club

Kitty’s Cosmopolitan Club brings back a little occasion to going out for cocktails. Beneath Crying Tiger in River North, the lounge combines a lush setting with tableside service, including Old Fashioneds prepared on a trolley. I appreciate a drink that makes an entrance.

The attention extends to the food, with indulgent snacks such as Dungeness crab cocktail, while the drinks offer enough invention to support the ceremony. The result is one of Chicago’s more enticing newer addresses for an evening that involves getting dressed, making a reservation, and enjoying the fact that somebody is taking care of you. Birthdays and dates are obvious excuses. A free Saturday works, too.

Bar Bambi

Katie Renshaw’s Bar Bambi brings color, personality, and a welcome sense of play to West Town. Opened in February 2026, her first solo project draws on experience at Chicago institutions including The Aviary and Moneygun, with a menu that allows her own style to come through.

The Miss Scarlet, for example, combines gin with lavender, cola spices, and Campari-raspberry sorbet among its ingredients. Other creations explore combinations involving mezcal, mango, and amazake, or chamomile and clarified coconut yogurt. The food deserves some attention as well, including salmon crudo with spicy nước chấm. It’s an ambitious collection of flavors in a room that looks like it’s enjoying itself.

Drama Club

Orange velvet, gold mirrors, tropical plants, tequila, and mezcal: Drama Club has a clear idea of a good time. Opened in July 2026 by the team behind Scofflaw, the Humboldt Park bar puts agave spirits at the center of a room with ample personality.

The collection provides plenty to explore beyond the usual margarita order, while weekend DJs help move the evening along. Its appeal is in that combination of a focused drinks program and a setting with some energy. Drama Club gives you permission to make a night of it, preferably with friends who appreciate both a good mezcal and the importance of staying for one more song.

Caché 310

Caché 310’s French name means “hidden,” which is helpful context when you’re trying to locate it behind BMO Tower. The West Loop lounge takes inspiration from the small drinking rooms of Paris, with a French influence running through the cocktail names, ingredients, and presentation.

The French Press puts its own spin on the espresso martini, combining vanilla vodka, Patrón XO Café, and coffee amaro with cold brew served tableside in a French press. The New Orleans blends elements of an Old Fashioned and a Sazerac, finished with a spritz of absinthe. The room’s intimate proportions and hidden location make the Parisian inspiration feel particularly appropriate. A little effort finding the door is part of the arrangement.

Charis Listening Bar

The playlist at Charis deserves more credit than background music usually gets. At this Bridgeport listening bar, vinyl is central to the experience, giving guests a reason to put their phones down and pay attention to something considerably more enjoyable.

The cocktails hold their own, with miniature martinis and an awamori creation involving rice milk and amaro among the drinks that have appeared on the menu. Named for the owner’s mother, the bar was conceived around the pleasure of sharing music, drinks, and conversation. That personal foundation suits the intimate space. The evening can be as simple as a good record, a well-made cocktail, and somebody you actually want to talk to.

Cantina Rosa

Erick Williams named Cantina Rosa for his grandmother, Rose, and built its drinks identity around another personal connection: the Mexican heritage of members of his team. At the Hyde Park bar, agave and sugarcane spirits provide the foundation for tropical cocktails with a clear sense of place.

The Jushu brings together mezcal, acacia honey, lime, and mango, while the Desert Spoon Swizzle combines sotol, rum, sorrel, lime, and mint. A frozen guava colada offers another appealing direction, particularly alongside mushroom empanadas. Named Eater Chicago’s Best New Bar of 2025, Cantina Rosa has the credentials to justify the trip and a story that makes the experience more meaningful. Family, hospitality, and a very good cocktail tend to work well together.

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Planning your next bar crawl? Catch up on everything that mattered at Tales of the Cocktail 2026, then compare notes with Haute Living’s essential cocktail bars on the Upper East Side and the best rooftop bars on the Las Vegas Strip.