Crafty Cocktails

These four lounges, hand-picked by concierge, have raised the bar for cocktails in Chicago.

Joni Kat Anderson
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Here’s a look at four lounges and bars, hand-picked by concierge, that have raised the bar for cocktails in Chicago.

Berkshire Room

The Berkshire cocktails

The Berkshire. Photo by Leigh Loftus.

If you’re looking for a sleek craft cocktail lounge, Logan Lawson-Parks, concierge at the Hyatt Regency Chicago, recommends The Berkshire Room. Named for the hotel that once stood on its plot, this River North hot spot is known for its boozy cocktails and boisterous, yet effectively soft and sexy, living-room-style lounge atmosphere. Here you’ll find a potent cocktail program that stands high as it probes the imbiber with a trilogy of decisions. Classic cocktails, barrel-aged concoctions, and a dealer’s choice—where you choose the spirit, profile, and glassware and let the cocktailians do the rest. Highlights include the bourbon-intensive “Weston,” complemented with pipe tobacco and Chicago’s own Dark Matter coffee essence; or our favorite, the “Continuous Negroni,” a classic take on the standard that’s aged in a Pappy Van Winkle barrel.

Lost Lake

Lost Lake cocktails

Lost Lake. Photo by Clayton Hauck.

Looking to venture beyond downtown? If so, concierges can’t get enough of Lost Lake, a fun, tropical oasis of a bar. This tiki-inspired lounge, helmed by celebrated mixologist Paul McGee, is a laid-back and friendly place that covers all of the tiki bases. From the banana-leaf paper on the walls and the piranha tank by the door to the cocktail list full of potent tiki drinks, this neighborhood gem delivers. Make sure to try their signature cocktail, the Lost Lake, featuring a heady mix of aged Jamaican rum, passion fruit, pineapple, maraschino, and Campari. If you’re feeling peckish, you can order some Chinese American bites from Thank You located next door.

The Violet Hour cocktails

The Violet Hour

Violet Hour

While the busy six corner intersection of North, Milwaukee, and Damen Avenues makes for a great night of bar hopping, W Chicago Lakeshore concierge Ramon Gomez says you’d be remiss not to slip into The Violet Hour, a sumptuously appointed speakeasy lounge. This craft cocktail mecca specializes in pre-prohibition style libations with a seasonally rotating cocktail list that is masterfully executed, right down to the type of ice in your glass (which is offered in eight different forms).

Three Dots and a Dash

Whenever Jonathan Rettemnier, concierge manager at 900 North Michigan Shops, has someone visiting from out of town, he always brings them to Three Dots and a Dash. A subterranean, post-WWII themed tiki bar in River North, this rum-focused, palate-cleansing paradise serves up innovative tiki-style drinks in signature, souvenir glassware. Enter through the alley and prepare to board the ship as you navigate their treasure map of a menu in search of rum-soaked, buried treasure. Enjoy a shareable option such as Zombie Punch, the bar’s eponymous selection, or the Jungle Bird.


Written By Amber Holst

Amber Holst is Vice President & Editorial Director at Concierge Preferred. A native Chicagoan, she’ll happily bend your ear about why Top Notch burgers are a must (as is an Original Rainbow Cone) and can often be found procuring milk candy in Chinatown after dim sum with her partner in crime or rooting on her beloved Green Bay Packers (yes, that’s right) at Will’s Northwoods Inn. Lover of cured meats, prosecco, and good old fashioned “slashies” she considers herself fortunate to be able to promote her hometown for a living. Fun fact? She can play the accordion.