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Entertainment for Every Taste

One of the best perks of the Magnificent Mile is the endless list of entertainment. There are comedy clubs, live music venues, theaters, dance companies and more on every block of downtown Chicago. 

The list of criteria can be extensive, which is why I’m here to help you narrow it down based on one key component: your favorite drink

Taste in refreshment is quite telling of a personality. From on-the-rocks to by-the-pint, personality traits are just as varied. When setting out for a fun-filled night of entertainment, you don’t want to get stuck in an ambiance of an Old Fashioned when you’re more of a Cosmopolitan character. 

In this blog, you will find the perfect pairing of place and personality to help you discover the right venue for your evening entertainment. 

  • The Comedy Bar

    PairingCraft Beer Flight
    Notes: Spontaneous, Witty, Authentic

    Okay craft beer lovers, let's start with you. Tucked away on the third floor of Gino’s East, The Comedy Bar awaits. Gino’s East is located in Chicago’s landmark LaSalle Street Cable Car Powerhouse and is home to Gino’s Brewing Company, offering signature craft beers that pair perfectly with a cheesy deep dish pizza. Make your way past the graffiti-covered second floor to the rustic-grunge venue complete with vintage bar chairs and exposed wood beam ceilings. 

    You are a beer flight fanatic: unafraid to go for it and try new things. A beer flight is like a brewery advent calendar with a surprise in each sip. The worst that can happen is 6 oz of a brew you don't love, but hey, one step closer to finding your new favorite! With a flight, you don’t know what to expect, but that’s the best part. As you sip locally crafted spontaneity, local improve takes the stage. From Comedy Brunch to the Tomato Throw Show, the Comedy bar sets the bar high for stand-up in the city. 

    Flight Favorites: 

    • Gino’s Pale Ale (GPA) - Belgian Pale Ale - Our most awarded beer, Belgium ale with a fruity, citrus hop aroma.
    • LaSalle Street Lager - German Heles Lager - Light traditional malt forward German lager, that finishes dry.
    • Witte Chicks Dig Me - Belgium Wit - Light, refreshing, wheat-based ale with a citrus and coriander aroma
    • Broken English ESB – Extra Special Bitter - Malt forward, yet balanced English style ale that pairs well with our deep dish.
    • Pineapple Imposter - Pale Ale - American pale ale with a fruity American twist.

    The Comedy Bar
    500 N LaSalle Street | 312-836-0499


  • Lookingglass Theatre

    Pairing: Paloma
    Notes: Surprising, Curious, Refreshing  

    “Oh my, how curious everything is!” - Alice
    Lewis Carroll, Through the Looking-Glass and What Alice Found There

    Since 1988, Lookingglass theatre has brought curiosity to life. Inside the historic Water Works Tower, Lookingglass Theatre has the opportunity to bring history and theatre together in new and unique ways. As it was once a visitors center, many guests enter the space for its famous history and are delighted to find a theatre, while others come for the theatre and are broadened by Water Works’ historical significance.

    The mix of visitors has helped create the company’s mission to entertain, teach, and perform to anyone who walks through their doors, no matter if they are from the Chicagoland area or visiting from around the world. 

    Now, let’s talk tequila: You are young at heart, inspired by learning and simple pleasures. There is a youthfulness to tequila drinks, whether they are reminiscent of college days or simple reminders of good times spent with friends. Tequila is a classically mixed into vibrant, fruity refreshments that leave you pleasantly satisfied with a surprising kick. Lookingglass is nothing if not surprising. From their space within Water Works to their distinctive performances, even the biggest theatre skeptic will find something to love about Lookingglass.

    Lookingglass Inspired Libation:
    Tequila and Mezcal Paloma with St. Germaine and Hibiscus. 

    “This drink, much like the space in the Water Tower Water Works, is a twist on a classic: It’s both refreshing and surprising. It’s surprisingly a little spicy but leaves you feeling refreshed!”
    - Lookingglass Mixologist Josh McCammon

    Lookingglass Theatre
    829 N Michigan Ave | 312-337-3665

  • Redhead Piano Bar

    Pairing: Classic Martini
    Notes: Old School, Sleek, Flirtatious

    The Redhead Piano Bar is for those who need a night of free-spirited pleasure. And let me tell you, the spirits here couldn’t be more liberated. With an impressive array of liquor options, this no-frills classic takes you back to old-school Chicago with the dimly lit room and live music escaping from the basement hideaway. Redhead is a hot spot for everyone from late night locals to business people letting loose in the Windy City. Piano legends and cocktails flow until the early hours of the morning. And trust us, the night never slows. 

    You’re a martini type. You are strong-willed and know what you like - and you never say no to a night out. But you have classy tastes and are deliberate in your choices. A night out to you requires the perfect ambiance and top-shelf talent in both the music and libations. You’re in need of a upscale lounge with your favorites bursting from the keys. Follow the flirtatious Redhead through the iron-wrought gate into a classy, comfortable atmosphere with a well-dressed crowd and prepare for a memorable night of live music and singing along to classic tunes with unabashed zeal.

    Don’t Miss It:
    Martini Mondays

    Redhead Piano Bar
    16 W Ontario Street | 312-640-1000


  • Chicago Shakespeare

    Pairing: Anything but Water
    Notes: Out of the ordinary, rule-bending, progressive

    Chicago Shakespeare invites you to expect the unexpected. Located along Chicago’s famous Navy Pier, Chicago Shakespeare Theater lives up to its namesake as a leader of theatrical innovation.

    In Globe-inspired halls, audiences wrap around the stage for an intimate experience. Every performance has outstanding elements of raw humanity: props are on stage and exposed, costumes are casual and practical, actors are interactive and genuine. There is nothing pompous or pretentious about this theater. It is, in a word, real. 

    Adaptations of Shakespeare are nothing new to the theater world. Here, the narratives push the boundaries and redefine what Shakespeare can be with dynamic stage direction, modern mannerisms, and vivid set design. 

    Still a skeptic? Lucky for you, Shakespeare’s plays makes up only a fraction of the theater’s productions. From eye-opening and vibrant shows to grungy hip-hop productions, each is a spectacle of innovation. Viewers are exposed to multi-genre influences, cutting-edge choreography, and exceptional talent.

    You, too, are a wild card. Some days you prefer wine and other days you reach for a rum and coke. Similar to the expression “it isn’t what you do, it’s who you’re with,” it's not the drink that matters: it’s that you are having fun and embracing the moment. You are intuitive and receptive to the fierce honesty in each performance as hidden narratives touch on critical social issues.

    Chicago Shakespeare Theater
    800 E Grand Avenue | 311-595-5600

  • Special Mentions

    Eno Wine Bar

    Pairing: Wine
    Notes: Relaxed, Intimate, Serene

    Eno Wine Room
    200 N Colombus Drive | 312-946-7000

    Chicago Jazz Philharmonic

    Pairing: Gin & Tonic
    Notes: Classy, Lively, Sophisticated

    Chicago Jazz Philharmonic
    1111 N Wells Street | 312-573-8932

    Broadway Playhouse

    Pairing: Manhattan
    Notes: Snazzy, Grand, Zealous

    Broadway Playhouse
    175 E Chestnut Street | 312-977-1700


    Pairing: Tarte Ale
    Notes: Funky, Abstract, Interactive

    Museum of Contemporary Art
    220 E Chicago Avenue | 312-280-2660


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