Things to do in Chicago this weekend — Chicago River Swim, Oktoberfest celebrations and more

CHICAGO – Chicago’s weekend calendar is packed with festivals, performances and historic firsts, offering something for every interest. From Oktoberfest celebrations and art fairs to a landmark swim in the Chicago River.

Here are some of the top events happening around Chicago Sept. 19-21.

What concerts are in the Chicago area this weekend?

Sept. 19: blessthefall at House of Blues Chicago

Sept. 19: Lorde at United Center

Sept. 19: Sextile at Outset

Sept. 19: Quinn XCII at Byline Bank Aragon Ballroom

Sept. 19: Big Wild at The Salt Shed Indoors

Sept. 20: Landmvrks at House of Blues Chicago

Sept. 20: Ethel Cain at The Salt Shed Outdoors

Sept. 20: Atif Aslam at Arie Crown Theater

Sept. 20: Wardruna at The Auditorium

Sept. 20: Goose at Huntington Bank Pavilion Northerly Island

Sept. 20: Pete Yorn at Thalia Hall

Sept. 20: Ramon Ayala at Allstate Arena

What sporting events are in the Chicago area this weekend?

Sept. 20: Northwestern womens volleyball versus Campbell

Sept. 21: Chicago Bears versus Dallas Cowboys

Multiple dates: Chicago White Sox versus San Diego Padres

What theatre and comedy shows are in the Chicago area this weekend?

Constellations

Dial M for Murder

Arnez J at Chicago Improv

The Twenty-Sided Tavern

TWIHARD! A Twilight Musical Parody

Leslie Jones at Geroge Van Dusen Theatre

What festivals are in the Chicago area this weekend? 

Wrigley Oktoberfest 

The Chicago Cubs will host their first-ever Oktoberfest this weekend, transforming a Wrigleyville lot into a three-day celebration of Bavarian culture. The family-friendly fest will feature live music, stein-holding contests, a dachshund parade and more, with tickets starting at $15.

Chicago Live! at Navy Pier

Chicago Live! returns Sept. 20-21 with more than 100 artists, theater groups and local organizations performing across five stages at Navy Pier. The free festival marks its fifth anniversary with world premieres, dance, music and a Saturday headliner set featuring Buddy Guy.

Jerk Seafood Vegan Fest 

Now in its ninth year, the Jerk Seafood Vegan Fest will highlight Caribbean flavors with jerk check, grilled seafood and a wide range of plant-based dishes. This event at Union Park aims to bring together some of Chicago’s top restaurants and chefs for a multicultural food experience.

Move at the Shed Fest 

Move at the Shed invites guests to design their own festival day with sessions ranging from yoga and meditation to dance and strength training. Visitors can also take part in community runs, wellness activities and open-air lounges with a community pass.

‘Move at the Shed’ kicking off Sunday | ChicagoNOW

Kicking off this Sunday, the first-of-its-kind, star-studded wellness and music festival is happening at the Salt Shed. It’s called “Move at the Shed” and features artists like Jamila Woods, Vic Mensa and Raveena, as well as yoga, meditation, dance, somatic breathwork, drum cardio, mat-based pilates, and more

Englewood Jazz Festival 

The Englewood Jazz Festival returns Sept. 16-20 to Hamilton Park with free performances celebrating the 60th anniversary of the Association for the Advancement of Creative Musicians.

Old Town Oktoberfest 

Old Town will launch its first Oktoberfest Sept. 19-21, filling Wells Street with bratwurst, pretzels, German beer and live music. The weekend includes brass bands, string ensembles, tribute performances and VIP options for festivalgoers.

West Loop Music and Art Fest 

The West Loop Music and Art Fest will turn five city blocks of Fulton Street into a sprawling showcase of art, food and live performances. The daytime event spotlights more than 100 vendors, while evenings bring DJs, bands a vibrant nightlife scene.

Clink and Sip Festival 

The Clink & Sip Festival will highlight BIPOC winemakers and distillers with tasking and chef-driven bites. Beyond sampling, the event celebrates representation in the wine and spirits industry with panels, vendors and community connections.

What other events are in the Chicago area this weekend? 

Teen Lit Night at Harold Washington Library 

Harold Washington Library will host Teen Lit Night on Sept. 19, an evening dedicated to young adult literature, music and art. The free event includes author meetups, live art, a silent disco and giveaways of books and themed merchandise.

Chicago River Swim

For the first time in nearly a century, the Chicago River will host an open-water swim on Sept. 21, featuring a two-mile course through downtown. About 500 experienced swimmers are expected to take part in the historic event.

Chicago River Swim returns this fall after 98-year hiatus | ChicagoNOW

For the first time in 98 years, the Chicago River will host an open water swim event this fall. The Chicago River Swim event has been approved by the city after officials denied the permit last year. It will take place on September 21 and feature 500 qualified swimmers. CEO of The Chicago River Swim Doug McConnell tells us more about it.