What Are the Must-Do Activities in Chicago from September 19-21?

This weekend in Chicago promises a vibrant mix of events, from competitive swims in the iconic river to music festivals featuring top-notch artists. Attendees can immerse themselves in local culture, enjoy live performances, or reflect on significant historical events. Whether you're a music lover, a film enthusiast, or simply looking to explore Chicago's unique offerings, there's something for everyone.

Last updated: 21 September 2023 (BST)

Key Highlights This Weekend

• Chicago River Swim: A historic open-water swim event.
• Riot Fest: A major music festival with over 80 acts.
• Kali Uchis: Grammy-winning artist performing live.
• Reeling 2025: Celebrating LGBTQ+ cinema with diverse screenings.
• Social Justice Stage: An event combining entertainment and activism.

Chicago River Swim: A Historical Event

On 21 September, the Chicago River will host its first competitive open-water swim event in nearly a century. Swimmers will compete in one- and two-mile races, starting from the Dearborn Street Bridge and finishing below the Clark Street Bridge. The event features notable athletes, including Glenview native and Olympic gold medalist Olivia Smoliga and Olympic bronze medalist Natalie Hinds, who advocates for water safety.

This unique event not only highlights athletes' skills but also aims to raise funds for A Long Swim, which supports ALS research at the Northwestern University Feinberg School of Medicine and local swimming programmes. Though registration for swimmers has closed, spectators are encouraged to enjoy the races from the Riverwalk.

Riot Fest: A Celebration of Music

This weekend marks the 20th anniversary of Riot Fest, taking place in Douglass Park. Renowned bands such as Blink-182, Green Day, Weezer, and Jack White headline the festival, promising an unforgettable experience for music lovers. Attendees can enjoy a variety of carnival rides, food vendors, and arcade games alongside the extensive music lineup.

The festival runs through 21 September and features over 80 acts, showcasing a blend of punk, rock, and emo genres. Tickets are available at the entrance, and the atmosphere is expected to be lively and engaging, making it a must-visit event for fans of live music.

Lorde Live at the United Center

On 19 September, Lorde will grace the stage at the United Center as part of her “Ultrasound” tour. With her latest album, “Virgin,” receiving critical acclaim, fans can expect a vibrant performance that encapsulates her artistic evolution. The concert will also feature opening acts The Japanese House and Chanel Beads.

This is an excellent opportunity for fans to witness Lorde's transformation into a more mature artist, as she showcases her unique style and compelling music. Tickets are available through the United Center's official website.

Kali Uchis: Two Nights of Enchantment

Catch the talented Kali Uchis on 22-23 September at the United Center. The Colombian-American singer, known for her Grammy-winning work and a massive following on Spotify, will perform tracks from her latest album, “Sincerely.” Thee Sacred Souls, an 11-piece band, will open for her, promising an energetic night filled with captivating performances.

With tickets starting at £73.65, those attending can look forward to an evening of rich melodies and engaging rhythms that highlight Uchis’s distinctive sound.

Reeling 2025: Chicago LGBTQ+ International Film Festival

This weekend also marks the beginning of the 43rd Chicago LGBTQ+ International Film Festival, Reeling 2025. The festival opens with the animated film “Lesbian Space Princess,” featuring the voice of Shabana Azeez. Over the course of the festival, attendees can watch more than 40 screenings, including feature-length films, documentaries, and shorts that provide a diverse representation of the LGBTQ+ community.

The festival runs through 28 September at Landmark’s Century Centre Cinema and Chicago Filmmakers, with tickets available from £15. This event offers an essential platform for LGBTQ+ stories and experiences, inviting viewers to engage with meaningful narratives.

Reflecting on a Legacy: “Trial in the Delta”

On 20 September, the Collaboraction Theatre will present “Trial in the Delta: The Murder of Emmett Till.” This powerful performance reenacts the 1955 court proceedings against Roy Bryant and J.W. Milam, who were acquitted despite later confessing to the crime. The show will be accompanied by a student creative showcase, featuring art from the inaugural Till Institute Summer Academy.

As this event takes place 70 years after Till's lynching, it serves as a poignant reminder of the ongoing discussions around racial injustice and historical memory. The performance is free, making it accessible for all who wish to engage with this vital piece of history.

Social Justice Stage: Art and Activism

This weekend, the Chicago Urban Art Retreat invites the community to come together for the Social Justice Stage, running from 20 September. This event combines entertainment with activism, featuring poet Blaq Ice and a lineup of artists including the 64th Street Beach Drummers and the Legendary Sax Preacher.

Justin Blake, the uncle of Jacob Blake—who was shot by police in Kenosha, Wisconsin—will also speak at the event. This gathering aims to raise awareness around social justice issues while providing a platform for local artists to express their creativity.

Logan Square Biennial House Walk

For those interested in architecture and history, the Logan Square Preservation will host its 35th Biennial House Walk on 20 September. This event allows attendees to explore some of Logan Square’s most architecturally significant homes and gardens, including seven residences in Palmer Square and the 1910 Holy Resurrection Serbian Orthodox Church.

Tickets start at £50 and provide a unique opportunity to appreciate the beauty and history of these notable buildings, while also supporting local preservation efforts.

Old Town Oktoberfest: A Taste of Bavarian Culture

Old Town will celebrate its first Oktoberfest this weekend, offering a delightful combination of German culture and local flair. From 19 to 21 September, attendees can indulge in traditional German cuisine, enjoy polka dancing, and participate in the Masskrugstemmen competition to see who can hold a stein the longest.

With a suggested donation of £5, this family-friendly event promises to be a fun-filled weekend, showcasing the vibrant spirit of the community.

Labubu Pop-up Event in West Town

This weekend, the Gangnam Market will host a Labubu pop-up event, celebrating the popular Chinese Pop Mart plush toys associated with Blackpink’s Lisa. The event features meet-and-greets with costumed Labubu characters, clothing, accessories, and even tattoo opportunities with artist Hunter Choa.

Running from 20 to 21 September, this free event invites fans and curious visitors alike to dive into a whimsical world of collectibles and creativity at Gangnam Market.

Conclusion

With such a diverse array of events happening this weekend in Chicago, there's no shortage of activities to engage in. From historical reflections and important social conversations to thrilling performances and cultural celebrations, attendees will have plenty of opportunities to connect with the community and experience the city in new ways. What event are you most excited to attend this weekend? #ChicagoEvents #WeekendActivities #LocalCulture

FAQs

What is the Chicago River Swim event?

The Chicago River Swim is a competitive open-water swim event taking place on 21 September, featuring one- and two-mile races in the Chicago River. It aims to raise funds for ALS research and local swimming programmes.

When does Riot Fest take place?

Riot Fest is being held in Douglass Park through 21 September, featuring over 80 musical acts across various genres, alongside carnival rides and food vendors.

Where can I watch the Reeling 2025 film festival?

The Reeling 2025 film festival runs through 28 September at Landmark’s Century Centre Cinema and Chicago Filmmakers, showcasing diverse LGBTQ+ films. Tickets start at £15.

What is the significance of “Trial in the Delta” performance?

This performance reflects on the legacy of Emmett Till and the historical court proceedings surrounding his lynching, aiming to engage audiences in discussions about racial injustice.

When is the Old Town Oktoberfest happening?

The Old Town Oktoberfest takes place from 19 to 21 September, featuring German cuisine, polka dancing, and community celebrations with a suggested donation of £5.