Meetings and events are exponentially more enjoyable when cocktails are involved, a tenet that's especially true when said cocktails are unique, innovative and served in stunning settings. Chicago's got plenty of all of the above.


Three Dots and a Dash (435 N. Clark St.)

Three Dots and a Dash

Whether you're in the business of Pirates of the Caribbean cosplay or, you know, something more normal, Three Dots and a Dash is your perfect destination. This clandestine, subterranean tiki hideaway peddles tropical cocktails that are sure to transport you and your cohorts to a beachy excursion befitting Jack Sparrow and his crew. Nestled down an alleyway in River North - don't fret, this alley is particularly clean and beautiful - Three Dots adds an element of fun and excitement to any event or function. Bring a group and stop by early to ensure you snag a booth, or reserve the extra lounge room by the host stand. For particularly enormous functions, Three Dots is also available for buyouts.    Private Parties inquiry


The Aviary (955 W. Fulton Market)

The Aviary

Clinking glasses gets a lot more interesting when the glassware is more complex than a game of Mouse Trap. One of the most innovative cocktail bars in Chicago, nay the world, is The Aviary, the boozy masterwork of the team behind internationally heralded Alinea and Next restaurants. At this slick, dimly lit Fulton Market spot, you'll feel more like you're at a buttoned up restaurant than a cocktail bar, complete with a cocktail "kitchen" viewable through a large glass wall. The heightened focus on craft and culinary technique involved in each cocktail, from chic tea infusions to elaborate fruity creations that look more like aquariums than cocktails, adds a serious wow factor for groups looking to raise the bar, so to speak, on their meetings.    Private Events inquiry


Watershed (601 N. State St.)

The Drifter (676 N. Orleans St.)

The Drifter

Deeming by the rising trend of underground speakeasies, you'd think Prohibition had actually been reinstated. Thankfully, that's not the case. But seeing as we can all venture to enjoy cocktails in offbeat, secretive settings without threat of being arrested for it, it's the best of both worlds. Mod speakeasies are one of the hottest facets in the cocktail world nowadays, be it a modern and glamorous setting like Watershed or a more mystical, borderline spooky spot like The Drifter. The former is an elaborate cocktail den tucked away below Pops for Champagne in River North. The focus here is on artisanal, locally sourced spirits and ingredients, stirred and shaken into a bevy of progressive house cocktails.    Contact: 312-266-4932   

The Drifter (pictured), meanwhile, looks and feels more timeworn, with a funky air to it reminiscent of gypsies and tarot card culture. You can find it beneath the Green Door Tavern, one of the oldest dining spots in town. Seeing as speakeasies are cozy, hushed and filled with intimate nooks and crannies, they make for apt business gatherings, with the added bonus of exoticism and mystique.     Contact:


Drumbar (201 E. Delaware Pl.)

I|O Godfrey (127 W. Huron St.)


When it comes to haute bar settings, the only thing cooler than an underground speakeasy is a bar that skews in quite the opposite direction, way up in the sky. One of the best rooftop bars in Chicago, ideal for group gatherings and corporate toasting, is Drumbar (pictured). Perched inside the Raffaello Hotel in Streeterville, right behind the majestic Hancock Tower, Drumbar keeps the focus squarely on drinks. And impressively modern drinks to boot, like the banana- and fennel-infused Chico Guapo, the Generally Mackin' splashed with "fajita seasoning," or the bourbon-based Hog Wild made with maple and soy. The bar is divvied into ample indoor and outdoor space, with the indoor areas resembling a polished parlor from the game Clue. The outdoor deck, meanwhile, affords an expansive view of the city skyline, along with numerous booths, chairs, and fire pits.    Private Events inquiry

If it's a chic South Beach-type setting you're looking for, meet at I|O Godfrey inside the Godfrey Hotel. With the largest retractable roof of any bar in the city, this spot is versatile and illustrious, boasting a warm sunny vibe bolstered by pristine cocktails both contemporary and classic. It's a pretty massive space, so you and your comrades will have plenty of room to mosey, mingle, and ooh and aww at the view.    Event Booking info


Game Room (12 S. Michigan Ave.)

Streeterville Social (455 N. Park Dr.)

Streeterville Social

All work and no play is a recipe for boredom. The uptick in activities at bars in Chicago makes it easy to mix a little business with pleasure, thanks to new spots like Game Room inside the Chicago Athletic Association hotel. Located on the second floor of the new hotel, Game Room features classic American cocktails in a large space filled with games like chess, bocce, shuffleboard and more. Think of them as good team-building exercises.

Then there's Streeterville Social (pictured), the newest and largest terrace in town. Located at the Loews Hotel, this massive addition features a grassy lawn with outdoor games like croquet and even giant Jenga. With 9,000 square feet of terrace space, there's more than enough room to kick back and relax with your colleagues over drinks and food, bookending any business chat with some friendly competition.    Contact: Elizabeth Romanucci,, 312-840-6626