What's Happening On The Rooftop?From live music to cocktail classes, there’s always something going on at Boleo. Stay tuned for the latest special events coming to your favorite rooftop bar in the Loop.

Saddle up and check out these specialty cocktails fit for an iconic headliner:Available May 15-17
Red Cup Kiss – Sir Davis Rye, sparkling lemonade, whiskey pour-over over shot, with a mini red Solo cup
takeaway
Honey Buckin’ – Sir Davis Rye, lychee black tea-infused honey syrup, lemon, cowboy hat garnish
Gin and Jolene – Empress Indigo Gin, spiced pineapple syrup, tonic
Shotgun Rider – Meili Vodka, Giffard Framboise, Brovo Orange Curacao, lime juice, soda

Giddy Up! A Beyoncé Takeover at Boleo
We’re throwing a rooftop celebration fit for Beyoncé herself, with live entertainment all weekend long and specialty cocktails inspired by Queen B.
Wednesday, May 15 | 3:00 PM – 6:00 PM
DJ Martin Foster will be spinning a Beyoncé-themed set.
Thursday, May 16 | 5:00 PM – 8:00 PM
DJ Martin Foster returns with more Bey beats.
Friday, May 17 | 3:00 PM – 6:00 PM
Daniel Harris will be performing an acoustic set of Beyoncé and R&B hits.
We've also got some special cocktails available for those who want to start the party before stage lights hit!

DJ Martin Brings the BeatsFeel the buena onda with DJ Martin’s smooth beats and vibrant tunes. Whether you're sipping cocktails or dancing under the stars, he brings the good vibes to our rooftop.
5pm – 8pm
May 28th
June 25th

Full Flamenco Show Under the StarsMay 17 | 5PM - 8 PM
Get ready for a breathtaking night of rhythm, movement, and soul as we bring the fire of Andalusia to life beneath the stars. This full flamenco showcase features an incredible lineup of performers who will ignite the stage with passion and artistry:
La Tiranta – Vocals that stir the soul.
Thomas Kimball – Masterful flamenco guitar player.
Featuring dancers:
Ruben Carlos Rodriguez
Nalanie Molina
Ronaldo Monge
La Rosa Oscura
Come early, find your seat, and prepare for an unforgettable experience.

Flamenco Under the StarsImmerse yourself in the fiery passion of Flamenco by La Rosa Oscura. With every rhythmic step, expressive gesture, and vibrant costume, this dynamic performance celebrates Spanish culture, energy, and emotion.
5pm - 8pm
May 17th
May 31st

Chicago’s Taste of the NationJune 27, 2025
6:00 pm - 9:00 pm
Chicago’s top culinary event returns for one night of bites, sips, and entertainment—all supporting No Kid Hungry. Over 50 of the city’s best chefs, restaurants, and mixologists will be featured. Boleo is proud to be part of the lineup.

Live Performance by Patrick JasperMonthly: 2nd and 4th Saturdays | 5pm - 8pmElevate your Saturday evenings with live music by Patrick Jasper. Catch his soulful performances on the 2nd and 4th Saturdays of the month from 5pm – 8pm.
Perfect tunes, rooftop views, and Latin-inspired bites await!

Happy HourTuesday - Saturday | 3 - 6pm
Beat the rush and head up to the rooftop early. We're serving gourmet bar bites with a Pan-Latin twist like our Pan con Chicharon Slider with crispy pork belly, Chilcanos with house-made Pisco and a selection of discounted wine and beer.

Non-Alcoholic Beverage Menu
Looking for something less boozy? Our spirit-free cocktails are just what you need.