Cocktail Hidden Gems in Chicago

If you know the Chicago city well enough, then you will then know that Chicago is fortunate enough to be home to some of the world’s top bartenders. Whether you’re in the mood for a classic mojito or Manhattan, or you’re hankering for over-the-top tiki-style cocktails with a wooden cup and bendy straws, we’ve uncovered a few cocktail bar gems for you to discover while in the Windy City. Each of these spots offer inspired creations, unique atmospheres and experiences that will keep you coming back for another sip.

The Matchbox

Chicago’s smallest bar, with the biggest charm - The Matchbox has been a beloved and iconic neighborhood bar in West Town for over 75 years. Located about an 8-min drive from Level Old Town, its known for crafting some of the better classic cocktails around. And, while you might struggle to get past other guests sitting at the bar to get an empty seat, the moment you sit down, you’ll feel right at home. Sip back and relax while you watch the The Matchbox bartenders shaking, stirring, and straining, and experience why this tiny bar has made such a big impression.

The Drifter Chicago
Photo courtesy of @thedrifterchicago

The Drifter

Drifter, a time capsule of throwback Chicago with standout cocktails and one of the city’s most unique drinking experiences, is an authentic 20s-era speakeasy located in the basement of the Green Door Tavern., About a 5-min drive from Level Old Town, The Drifter is a real life Prohibition era speakeasy serving up a rotating list of over 100 cocktails presented on Tarot cards and nightly performances ranging from belly dancers to music to pop-up variety acts.


Housed in a historic Louis Sullivan building, Celeste is Chicago’s latest late-night bar featuring three uniquely appointed floors to enjoy craft cocktails and seasonally inspired food. The welcoming first-floor bar offers a casual neighborhood feel with resident DJs. The Deco Room, located on the second floor, spotlights craft cocktails, rare vintages, and hand-selected barrels. While the fourth-floor Roof Garden offers a year-round escapist experience decorated with floral-print Victorian furniture, tropical greenery and vine-covered brick walls. Choose your own adventure – cocktail edition.

Three Dots and a Dash

Three Dots and a Dash
Photo courtesy of @threedotsandadash - The Bamboo Room

Enter through a back-alley entrance into a portal to one of America’s best-built tiki bars – Three Dots and a Dash. Hidden below the bustling streets of River North,Three Dots and a Dash is Chicago’s premier tropical cocktail bar led by craft cocktail expert, Kevin Beary. Here you’ll also find The Bamboo Room at Three Dots and a Dash -a bar-within-a-bar concept for a more intimate experience where they offer a guided senses tour through the world of rum and feature exquisite tiki cocktails prepared with fresh-pressed juices and house-made syrups.


A short drive from Level River North, you’ll find Kumiko in Chicago’s West loop - a Japanese dining bar boasting incredible cocktails and spirits blended with Japanese ingredients and techniques and exquisite food to pair. Star bartender Julia Momose presides over this cocktail bar with Japanese heritage décor to express elegance, commitment, and passion. The menu ranges from light to dark, allowing guests to sip rare and fun ingredients such as Bermutto, a style of vermouth, but using sake and rice shochu as the base.

The Money Gun Chicago
Photo courtesy of @moneygunchicago


Looking for comfortable, classic cocktails and throwback bars with ‘90s hip-hop? Look no further. Located under the green and pink line el tracks in the West Loop, Moneygun is known for its good ambiance and outstanding quality cocktails. If you are in the mood for “Classic cocktails, and no bullshit”, this 90’s hip-hop oasis should be your pick. Sip on classic favorites from mojitos and mai tais to long island iced tea and cosmopolitans. In the warmer months, you’ll also find a massive backyard patio with bocce that location shares with their sister restaurant, Saint Lou’s Assembly, next door. Find Moneygun about a 6-min drive from our Level River North location.