Craziest Chicago Cocktails

by Kara Machowski

Mr. Nice Guy and others at Apogee

Apogee has quickly become one of my favorite spots in Chicago. The lounge is located in Chicago’s prestigious River North on the top of the Dana Hotel and Spa. Apogee has every right to be pretentious, however they are anything but that. Their famous cocktail, the Mr. Nice Guy (serves two), is served in an actual bong that is accompanied by smoking flower placed in the chamber and a bouquet of flowers poking out the top, you know, like when you used to tell your mom that it was just a vase? Apogee, decorated in dark oak and mid-century modern chandeliers, is located on the rooftop of the hotel and offers breathtaking views of the city along with an outside sitting area adorned with sleek comfy couches. Don’t forget to check out the rest of their menu, with drinks like the World 3-4, presented in a ceramic toadstool mushroom and the Nymph which includes a frozen in place flower and an adorning butterfly on top.

The Zombie and others at Three Dots and a Dash

I feel like there is no talking about crazy cocktails in Chicago without the mention of Three Dots and a Dash, which is why it made our list. Located just blocks from Apogee in River North, Three Dots is a must-visit for locals, transients and those who are just visiting. Down a darkened alley way is where you will find the entrance to the speakeasy. Make sure to have reservations, as you don’t want to find yourself in the line in the middle of the alley to enter, especially during the winter months. Once inside, you will travel down a dim stairwell illuminated by blue lighting and perched above you are carvings of skulls reminiscent of the Catacombs in Paris. Three Dots has a small seating capacity which is why some nights its impossible to enter without reservations. Once seated the inviting waitress in island attire will fetch you glasses of water and goes over the menu, which includes single served cocktails all the way to the smoking Treasure Chest that serves 8 people. My favorite cocktail here is the flaming Zombie, which serves 3-4, and is served in a glass skull and is actually on fire. It is infused with Jamaican rums and has strong hints of cinnamon and lime that make your senses fully aware of all the alcohol that makes up this boozy cocktail.

The Silly Rabbit at The Sixth

The Silly Rabbit at the Sixth, located in Lincoln Square, is brought to you by Benjamin Schiller, who is also the beverage director at Apogee Lounge. This cocktail is perfect for anyone who truly appreciates the flavors brought out by colorful infused ice cubes that compliment the drink more as they melt. The cocktail is not only appeasing to the tastes, but also visually. Each iced cube is flavored just like your favorite childhood cereal, Trix, and colored to match. Gin is poured over the cubes, causing them to melt and allowing you to taste the rainbow. Benjamin Schiller was recently named “Best Mixologist” of the Jean Banchett Awards and finished first in the mixology competition hosted by Bon Appétit and we only expect more great drink innovations from him to come.

Gray Garden at Cindy’s Rooftop

Cindy’s Rooftop has surely risen in popularity throughout the years, often times the line to enter extending past the Athletic Associations lobby and spilling onto the streets of Michigan Avenue. The rooftop, while not the tallest in the city, offers exceptional views of Grant Park, Chicago’s famous Bean and the Lakefront. Once inside, unless you plan to dine, you can skirt past the hostess to the main bar and I recommend trying the Gray Garden. It is made up of Tito’s, Dolin Blanc, crème de violet, Emperor’s jasmine pearl tea, lemon, embellished with an orchid and has a very refreshing light lavender taste that actually tastes like a lush garden. Once you have your drink in hand, head outside to take a glance at the view that Cindy’s has to offer. Also make sure to check out the walls inside of the elevator that lead up to Cindy’s from the hotel lobby and you’ll notice that it is encased in basketball wood flooring from the original gym when the hotel was the Men’s Athletic Association.

The Pornstar at the Disco Chicago

Now this cocktail should come with its own entourage, or well, typically does. Perched above Celeste, Disco is on the third story in River North’s club district and is just as difficult as the its late predecessor, Studio 54, to enter -so I recommend dressing the part to get in. There is a separate line to enter the Disco than Celeste so also make sure that you’re in the right line or else the bouncer may look at you with that southern ‘you dear thing’ stare. Once you make it inside the Disco, you’ll find it is decorated with light up dance floors, plush furry couches and giant disco balls that will definitely bring out your disco fever. Now that you are ready to get down, it is time to order their signature cocktail, the Porn Star. The Porn Star is a frozen martini with vodka, cuvée, passion fruit puree, vanilla syrup, lime juice and a shot of bubbly on the side served in an actual take-home disco ball. Did I mention that they make for the opportune dance floor selfie?

The Big Kahuna at Mahalo

Mahalo is located in the heart of Wicker Park and is a fresh breath of summer, any time of the year. Mahalo is a two level restaurant and is decorated like an upscale Hawaiian tiki bar, with white wood workings, pineapple wallpaper and neon lighting, the drinks aren’t the only thing that I come here for. With a completely Polynesian inspired menu you’ll find poké bowls, ramen, lots of tuna and some of my favorite cocktails in the city. The Big Kahuna is their most popular and is served in a pineapple, fit for two making it the perfect way to forget whatever temperature it is outside. If you are lucky enough to visit Mahalo in the warmer days of the year I recommend checking out their rooftop that is flush with sunlight and will make you forget that you are in a metropolitan city at all. Also try their piña colada, topped with toasted coconut and just the right amount of tropical love.

Booty Collins Punch Bowl at the Flamingo Rum Club

Named one of the top ten places to check out in Chicago, the Flamingo Rum Club is also serving up a cocktail that made it to the list. Inside the rum club flamenco dancers draped in jeweled bras commence as the night begins to heat up in Chicago. The next thing you know you have a giant golden flamingo on fire. It is being brought out by one of the beautiful waitresses inside the club with banana leaf wall paper and reminds you of Havana nights, even in the midst of February. That’s what the nights are like at the Flamingo Rum Club when you order the Booty Collins Punch Bowl. Oh and if you have trouble finding the place, it’s the building in River North that has the giant pink flamingos painted on the side of it.