I Luv Chicago

Your Guide to Upcoming Chicago events

ENDGAME” AT FACILITY THEATRE

Samuel Beckett’s Tragicomic Tale On Stage May 22 – June 29, 2025

 

ENDGAME, by Samuel Beckett, explores themes of existential despair, isolation, and the cyclical nature of life. The relationship between Hamm, a blind and paralyzed man, and Clov, his servant, reflects the dependence and powerlessness inherent in human existence. Their repetitive dialogue and occasionally hilarious routines suggest the futility of attempting to find meaning or escape from their circumstances.

The production runs May 24 – June 29, 2025 (previews May 22 and 23) at Facility Theatre, 1138 N. California Ave., with performances Thursdays, Fridays, and Saturdays at 7:30 p.m. Tickets (suggested donation of $30) are now on sale at www.facilitytheatre.org

 

An Evening with Heather Headley

June 3, 2025
Symphony Center

Tony and Grammy Award winner Heather Headley joins the CSO for a night of music from her celebrated 25-year Broadway career.

Groundbreaking silent film series with live music

Projecting Homosexuality: Queer and Trans Visions from Cinema’s First Decades

at FACETS Film Forum, Wednesdays, June 4-25

Series organized in conjunction with blockbuster exhibition,

The First Homosexuals: The Birth of a New Identity, 1869-1939

 which continues at Wrightwood 659 through July 26

In conjunction with its blockbuster new exhibition, The First Homosexuals: The Birth of a New Identity, 1869-1939, Wrightwood 659 is collaborating with FACETS Film Forum to commemorate Pride Month with Projecting Homosexuality: Queer and Trans Visions from Cinema’s First Decades.  Predominantly showcasing silent films, Projecting Homosexuality will illuminate gems from early 20th century queer cinematic history at FACETS, 1517 W. Fullerton Avenue, Wednesday evenings, June 4-25, 2025, as curated by Dr. Laura Horak, Professor of Film Studies at Carleton University and director of the Transgender Media Lab and Transgender Media Portal. Each evening will feature an introductory speaker and live musical accompaniment; the opening program includes remarks by Dr. Horak, along with a pre-screening reception, Wednesday, June 4, 7:30pm

Jun 5, 2025, 7:30pm CDT
Award-winning journalists Jake Tapper (CNN) and Alex Thompson (Axios) discuss their new book, Original Si
City Winery Presents

Artist

One Of A Kind: The Eddie Levert Show
June 6:  6 p.m; or
June 6:  9:30 p.m
 

Bea Hive Bash

A 1960’s-themed celebration honoring the legacy of Beatrice “Bea” Spachner, the leader responsible for revitalizing the historic Auditorium building in that decade 

On the historic stage of The Auditorium, Friday, June 6 at 7:30 PM

Bust out your mini-skirts, tie-dye, and go-go boots for the most far-out party of the summer, The Bea Hive Bash at The Auditorium (Chicago’s Landmark Stage® at 50 E. Ida B. Wells Drive). Celebrating the legacy of Beatrice “Bea” Spachner, the patron responsible for rescuing the historic building from being demolished in the 1960’s, this year’s iteration of The Auditorium’s annual summer party is a fab 60’s-themed bash paying homage to The Auditorium’s triumphant grand re-opening night in 1967. Held on the theater’s iconic stage, the party features creative cocktails, delicious food, an exclusive silent auction, and a live performance by the acclaimed Beatles cover band, Britain’s Finest. Can you dig it? The Bea Hive Bash is Friday, June 6 starting at 7:30 PM. Tickets start at $135 in recognition of The Auditorium’s 135th anniversary this year. Proceeds from the event will benefit The Auditorium’s three primary missions: restoring the historic Auditorium building, programming world-class presentations on stage, and engaging with the greater Chicago community. Tickets are available now at auditoriumtheatre.org or by calling The Auditorium’s Ticket Service Center at 312.341.2300

Pro Rodeo

Sonny Acres Farm in West Chicago is proud to announce the return of the 3rd annual Pro Rodeo June 13-14 and 20, 21, 22. Due to overwhelming demand, the family-favorite amusement farm has added a second weekend of performances to add to the fun, wowing audiences with a mix of world-class performances including Bareback Riding, Steer Wrestling, Saddle Bronc Riding, Girls Breakaway Roping, Cowgirls Barrel Racing, Bull Riding and more. In partnership with Big Hat Rodeo, the Midwest’s premier Pro Rodeo production company for over 100 years, the event of the Summer will offer families and fans a chance to enjoy a mixture of traditional rodeo competitions and world-class entertainment performances. Renowned Trick Rider and Roman Rider Dusti Crain Dickerson will perform her specialty act – standing atop two running horses simultaneously wowing crowds with spectacular maneuvers, including a jaw-dropping fire jump audiences will need to see to believe. Guests will also enjoy access to amusement rides, live DJ and musical entertainment, a petting zoo, full bar, outdoor grill and more. Tickets are available online

NPR Music’s Tiny Desk Contest is heading back on the road! Join us this summer as we travel to 10 cities for a one-of-a-kind concert. New this year, each stop will feature a different surprise Tiny Desk alum headliner, plus the 2025 Contest winner and an up-and-coming artist from each city.

Sammy Obeid

Saturday, July 5, 2025 at 6:45 p.m. and 9:00 p.m.

Sunday, July 6, 2025 at 5:00 p.m.

Tickets: $31 – $65

Lebanese-Palestinian American comedian Sammy Obeid was born in Oakland, California, and double majored in business and mathematics at UC Berkeley before turning down a job at Google to pursue stand-up comedy.

Now the host of 100 Humans on Netflix, Obeid has also appeared on NBC’s Last Comic Standing and America’s Got Talent, as well as Conan on TBS. He is best known for his world record of performing comedy 1,001 nights in a row—a feat featured in both Time magazine and The New York Times.

An Evening With Masood Boomgaard & Self-Help Singh

Sunday, July 13, 2025 at 7:15 p.m.

Tickets: $22 – $45

South African comedian Masood Boomgaard returns to the United States with his brand-new live experience, “An Evening with Masood Boomgaard and Self-Help Singh”—a unique double dose of hilarity, wisdom and wonderfully unapologetic real talk.

Best known as the mind behind the viral sensation Self-Help Singh, Boomgaard has built a cult following around the world with his deadpan delivery, mock-spiritual guidance and soul-crushingly honest advice. The Self-Help Singh character is a satirical take on the over-saturated self-help industry, offering painfully funny truths instead of feel-good fluff. Think Deepak Chopra—if he had zero interest in your success.

Now, in this new two-in-one comedy experience, fans will get more than just the Singh persona. For the first time on a U.S. stage, audiences will also meet the real Masood Boomgaard—comedian, world traveler and the man behind the madness. Boomgaard pulls back the curtain to share stories from his life, his upbringing in South Africa and his journey performing stand-up across more than 20 countries. Expect sharp insights, hilarious cultural commentary and behind-the-scenes tales from a career built on turning awkward truths into comedy gold.

This is more than a comedy show—it’s a demotivational awakening with a deeply personal twist.

Whether you’re a long-time disciple of Self-Help Singh or just someone who enjoys a good laugh at the absurdity of life, An Evening with Masood Boomgaard and Self-Help Singh promises a night of enlightenment, entertainment and existential despair—in the best way possible.

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