Chicagoans hold a few things sacred: food, sports, sunny days, good drinks, and finally, an undefeatable restaurant or bar concept. Whether it’s through a distinctive atmosphere, an appealing performance lineup, or delectable bites that pair perfectly with a signature cocktail, here are some of the most unique bars in Chicago to spend an unforgettable evening.


500 N Clark St #465, Chicago, IL 60654

Located on the lower level of Jaleo, you’ll find Pigtail, a speakeasy featuring Jamon and top-notch cocktails. This cocktail bar marries two loves of Chef José Andrés: jamón ibérco and delicious cocktails. Jamón Ibérco, or Iberian ham, is cured pork leg that has a sweet taste and pairs perfectly with a variety of different cocktails. Whether you’re looking for something “rich and bold”, “aromatic”, or “revitalizing”, we can guarantee that Pigtail is going to become a new favorite on your weekend rotation!


Lost Reef

964 W Belmont Ave, Chicago, IL 60657


If you follow all the cool things happening in Chicago, then you know the city’s first aquatic lounge has just opened. Tell me now, do you love the deep ocean, corals, colorful fish, and hidden treasure? Because that’s all Lost Reef is about. Step into a dreamlike environment with aquariums around the space and explore their seafood-led menu varying from fresh sashimi, sushi, to hot plates. As of drinks, Lost Reef is ready to sweep you off your feet with an extremely creative, colorful, and tasty cocktail menu.

The Pink Squirrel

2414 N Milwaukee Ave, Chicago, IL 60647

Being from Chicago, we all lean into being Midwestern, right? At the Pink Squirrel, take a step back in time and enjoy this retro atmosphere complete with Duckpin bowling, vintage fixtures, and booze-filled milkshakes and hand-crafted cocktails. If your group is looking for a cocktail to enjoy together, order up a Disco Duckie or a Flying Squirrel Cocktail Wheel to put a whimsical spin (literally) on your drinks for the evening.


630 W Lake St, Chicago, IL 60661

If you’re looking for something outside the standard cocktail list (sorry, Old Fashioneds), check out Kumiko. This Japanese dining bar in the West Loop features tons of Japanese drinks like sake, different beers, and unique cocktails. If this is your first visit, try one of their flawlessly put-together sake flights. With sweet, savory, and tangy flavors, you won’t feel like anything is missing as you relish in the different flavors that each sip of sake brings. Finally, Kumiko is also a pioneer in Chicago’s spirit-free scene. Therefore, even if you’re not a heavy drinker, you will still have a tasty time at Kumiko!


12 W Elm St, Chicago, IL 60610

What once served as a lobby bar during the roaring 20’s has since become cocktail lounge, Sparrow. Found under a towering apartment complex in the Gold Coast, Sparrow takes inspiration from the Art-Deco period, and continues to serve up uniquely styled cocktails to this day. Here, you’ll find their signature, “La Floridita”, which combines white rum, maraschino cherries, lime, and grapefruit for the perfect, citrusy sip. 

Flight Club

111 W Wacker Dr, Chicago, IL 60601

You’ve been bowling and you’ve played cards, but when is the last time your group of friends went out to play darts? At Flight Club Chicago, groups of up to 12 can enjoy “fast-paced” games while sipping on hand-crafted cocktails. Pair a signature cocktail like the Butterfly, Iguana, or Royal Lion with some healthy competition against your pals. Flight Club also hosts happy hours and exciting lunch breaks, so there’s always a new event to look forward to. 

Kaiser Tiger

1415 W Randolph St, Chicago, IL 60607

When lawn games are your thing, you cannot let the changing Chicago seasons stop you. At Kaiser Tiger, enjoy bocce in the summer and everyone’s favorite Winter Olympic sport when it gets cold out – curling! No matter what the temperature is, enjoy Kaiser Tiger with a cocktail in hand and the warm feeling of beating your friends at a game you’ve probably never played before. You’re not likely to find this anywhere else near you!


The Green Mill

4802 N Broadway, Chicago, IL 60640 

Originally open during the Prohibition era, the Green Mill is one of Chicago’s most iconic Jazz bars. Fun fact: this place used to pay off police officers to stay open. Now, you’ll find music and events seven nights a week with no “egg white cocktails or mojitos”, and a strict cash only policy. The Green Mill is rich with history, always entertaining, and closes at the strict 1:11 AM Monday through Thursday! 


112 W Grand Ave, Chicago, IL 60654

At the intersection of art, dining, music, and drinks, you’ll find Arbella. This contemporary speakeasy features signature cocktails that range from “tipsy” to “texting your ex” to “dancing on tables”. The food at Arbella is also a huge highlight with a menu full of favorites that have the Arbella touch like cast iron octopus, Arbella barbacoa tacos, or a savory shrimp scampi gratin.

Featured Image: Lost Reef

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