Photograph: Kyle Flubacker

7 Chicago bars that offer next-level entertainment

The weather outside is frightful, so batten down the hatches at these bars that serve their drinks with a side of fun

Morgan Olsen

Winter isn't exactly the season for barhopping. We much prefer to take off our puffy jackets (and scarves and mittens) and get cozy until the bartender kicks us out at the end of the night. Some of the best bars in Chicago are perfect for doing just that—and they're sweetening the deal with live entertainment, from tarot-card readings and drag performances to bouquet-making classes and museum exhibits. Snuggle up, because you'll want to stick around these Chicago cocktail bars that serve their drinks with a side of entertainment.

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Chicago bars with live entertainment

  • Lincoln Park

Decorated in baroque wallpaper, purple velvet drapes and brass chandeliers, this goth lounge will have you feeling like royalty, no matter how many slush puddles you trekked through to get there. The cocktail menu is equally regal, with concoctions sporting names like the Virtuous Queen, made with lavender-infused gin, Campari, rose vermouth and a rosemary-lavender tincture.

Stay for: After knocking back a few swizzles, do some soul-searching with a palm or tarot-card reading, available Wednesday through Sunday, from 8pm to midnight. Here's hoping there's no hangover in your immediate future.

  • Wicker Park

There's no shortage of fascinating cocktails at Machine, where beautiful glassware and over-the-top garnishes shine. You won't regret ordering the purple-hued Caged & Infused, a blend of butterfly-flower–tea gin, lemongrass, maraschino liqueur and lemon, topped with a violet-flavored candy cage you can break apart using the tiny hammer that's served with the drink. 

Stay for: When you step inside, you'll notice (and smell!) Machine's in-house flower shop, stocked with the freshest blooms available. If you wish, a pro florist will come to your table and build a breathtaking, this-will-look-great-in-our-foyer bouquet that you can take home.

  • Cocktail bars
  • Ukrainian Village

Named in honor of building owner and former bar maven Mary Kafka, Queen Mary Tavern is a self-proclaimed time capsule that introduces modern-day imbibers to the old-time drinking traditions of sailors. Set down an anchor and stay for a glass or two of the Daily Grog, a rotating punch that's garnished with fresh citrus and just enough spice to thaw your weary bones. 

Stay for: On Tuesday evenings at 8pm, curl up for movie night, with a featured flick on the drop-down screen at the back of the bar. The staff goes all out with themed cocktail specials and flavored popcorn. And with movies like Ghostbusters and Hairspray on the docket, there's plenty of fun to be had.

  • American creative
  • West Loop

Hidden behind a bespoke flower show on Randolph Street, this expansive two-story bar and restaurant is one of the West Loop's funkiest late-night destinations. Grab a table in the intimate first-floor Library and order some short-rib beignets for the table before deciding on your first round of cocktails—we recommend the spicy Desert Rose, with tequila, jalapeño-infused mezcal, tangy blood-orange juice and Tajín-agave syrup.

Stay for: Starting around 7:30pm every night but Monday, Library guests are treated to live throwback entertainment about every 30 minutes or so. On any given evening, you might see a soulful jazz cabaret singer, a sultry burlesque dancer, a drag vocalist or even an awe-inspiring fire-breather.

  • Contemporary American
  • Streeterville

Helmed by the all-star chef Jason Hammel (Lula Cafe) and located on the first floor of the Museum of Contemporary Art, Marisol is the kind of restaurant that every cultural institution deserves. The bar program rocks, too, offering happy-hour deals Tuesday through Friday, from 4 to 6pm, in which select cocktails, wines and beers are only $7 a pop. 

Stay for: Expert guides from the MCA offer one-hour private tours of the museum as a combo pack with Hammel's happy-hour deal. Available for groups of five to 20 people Tuesday through Friday, from 3 to 7pm, this bargain comprises a complimentary cocktail and a hosted tour based on your party's interests.

  • Logan Square

From the hilarious, Chicago-based minds behind Cards Against Humanity comes this 14,000-square-foot, full-service bar and restaurant, which will open on January 10. The menu is inspired by European sidewalk cafes where locals might sidle up to play a game with friends, so expect board-game diversions as well as cocktails and small plates with an international flair.

Stay for: Every reservation includes access to the building's old bank vault, which has been converted into a massive library that's stocked with hundreds of games, from Monopoly and Scrabble to new indie games and, of course, Cards Against Humanity.

  • Near South Side

Outfitted with opulent chandeliers and decorated in jewel-toned hues, Lips is a drag castle fit for a queen. From Wednesday evening to Sunday evening (and Sunday brunch), your dining-room reservation includes a show with your meal, but insiders know the no-cover bar always welcomes walk-ins, so perch there to watch the performance and—why not?—sip frozen cosmos, pear martinis and lemon-drop shots. 

Stay for: Of course, you're here to watch the ladies of Lips shimmy, sashay and strut their stuff across the stage. Local legend Ruff N' Stuff hosts a gospel-themed brunch on Sundays at 11:30am and 2:30pm, while Thursday nights are devoted to celebrity impersonations of Lady Gaga, Katy Perry and other divas.

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