What's On in Chicago Today — Monday, June 29
What's On in Chicago Today — Monday, June 29
Live Music & Concerts
Elujay / Khalil @ Empty Bottle: If you are hunting for a set that defies easy categorization, this pairing at the Empty Bottle is the perfect choice. Elujay brings a smooth R&B flair while Khalil adds his own unique edge, creating a genre-blending soundscape that feels distinctly modern. It is a fantastic Tuesday-night fix for music lovers who appreciate high-energy performances without the usual hefty ticket markup. Tickets start from roughly $21.
Madison Beer: the locket tour - MOVED TO HUNTINGTON BANK PAVILION @ Huntington Bank Pavilion at Northerly Island: Major venue shuffles are always a topic of conversation, and this move to the outdoor pavilion feels like a key upgrade for fans. There is nothing quite like seeing a pop concert under the stars with the Chicago skyline as a backdrop. Prepare for a massive production and a high-tide crowd ready to sing along to every chorus. This is the definitive summer pop experience on the lakefront.
Tiny Desk Contest On The Road 2026 with Cure For Paranoia... @ Thalia Hall: Bringing the prestige of NPR’s legendary contest to one of the city’s most historic interior spaces. Seeing a winner from the Tiny Desk contest perform in a cavernous room like Thalia Hall usually results in a masterclass in raw, loud, and emotive indie rock. It captures the spirit of discovery that the contest is famous for. At roughly $35.60, it offers incredible value for a night of professional, breakout talent.
FALCO & BOOK PLAY JERRY GARCIA @ Garcia’s Chicago: Nostalgia fans and jam band devotees will feel right at home mimicking the Garcia classics with a polished ten-piece band. It is a musical tribute that respects the heritage of the Grateful Dead while adding a fresh, energetic spin. If you are missing the tactile feeling of a guitar-heavy concert, Garcia’s delivers that specific jam-band chemistry in spades.
Dead Pink Radio @ Reggies Music Joint: For those who prefer grit and authenticity over polished stages, look no further than this intimate venue. Reggies has a reputation for hosting acts that are bubbling just beneath the mainstream surface, and Dead Pink Radio is no exception. Get ready for a rowdy, living-room vibe where you are practically in the band's lap. It is the ultimate underground Chicago experience.
Comedy & Theater
The Second City Mainstage 114th Revue @ Second City-Chicago: This is the institutional experience every Chicago visitor needs to tick off their bucket list. The 114th Revue keeps the legacy of political satire and improvisation alive by dissecting current events with razor-sharp wit. Roommates and date-night regulars alike will appreciate the classic feel of the mainstage. Just keep the door policy in mind: minors must be accompanied by an adult to enter the theater.
The Best of The Second City @ Second City-Chicago: Tired of sitting through a whole hour-plus show to find one or two laugh-out-loud bits? This truncated version rounds out the funniest lines from their recent runs into a tight, high-octane set. It is the perfect palate cleanser after a heavy Monday, ensuring you leave with a smile on your face and no buyer’s remorse.
Arts & Community
Balloon Museum | EmotionAir - Art You Can Feel - Chicago @ The Fields Studios: Prepare for a brain-tingling adventure that goes far beyond just visual sight. This installation manipulates air itself to evoke specific emotions, creating a tangibly responsive art piece that is impossible to ignore. It is a quirky, low-key community event that proves Chicago’s creativity extends into avant-garde, sensory experiences. It is a soothing counterweight to the high-energy noise of the music venues.
Local Tip: If you plan on hitting the Madison Beer show at Huntington Bank Pavilion, parking is notoriously difficult in the summer months. The Metra Electric Line is your best friend here; take the Museum Campus exit to avoid the expensive lot lines and the dreaded circling-for-a-spot parade.
Browse all Chicago events → stungevents.com