19 Things to Do in Chicago This Week · June 4–7, 2026

Music & Nightlife

Bryan Callen at Chicago Improv

Stand-up comedian Bryan Callen performs four shows over the weekend at the Chicago Improv.

Friday, June 5, 2026 · Chicago Improv, Chicago

Beyond Wonderland Preparty: LAYZ

18+ Beyond Wonderland preparty with LAYZ at Concord Music Hall, doors at 10 PM.

Friday, June 5, 2026 10:00 PM · Concord Music Hall, Chicago

Tyler Hilton & Kate Voegele: Celebrating the Music of One Tree Hill

Tyler Hilton and Kate Voegele celebrate the music of One Tree Hill live at City Winery Chicago, with special guest Gina Miles.

Friday, June 12, 2026 7:30 PM · City Winery Chicago

Outdoors & Active

Kayak & SUP Rentals at Northwestern Sailing Center

Northwestern Sailing Center now offers kayak and stand-up paddleboard rentals on Lake Michigan for all skill levels.

Saturday, June 6, 2026 · Northwestern Sailing Center, Evanston

Shakeout Run Before 13.1

Pre-race shakeout run in the West Loop with Read & Run Chicago and Family Style RC ahead of the Bank of America Chicago 13.1.

Saturday, June 6, 2026 9:00 AM · West Loop, Chicago

Free Events

Swimmers Installation on Michigan Avenue

Public art installation of swimmer figures takes up residence along Michigan Avenue this summer.

Friday, June 5, 2026 · Michigan Avenue, Chicago

American Writers Festival

Free two-day literary festival co-presented by the American Writers Museum and Chicago Public Library featuring in-depth conversations with diverse writers.

Saturday, June 6, 2026 8:00 AM · American Writers Museum, 180 N. Michigan Ave., Chicago

Sports

Bank of America Chicago 13.1 Cheer Zone

Join Read & Run Chicago and Family Style RC at the official cheer zone for the Bank of America Chicago 13.1 half marathon.

Sunday, June 7, 2026 7:00 AM · Chicago

Date Night

The Jazz Room: A Journey to the Heart of New Orleans

Immersive jazz experience at The Den Theatre transporting audiences to the heart of New Orleans with live performance.

Sunday, June 7, 2026 · The Den Theatre, 1331 North Milwaukee Avenue, Chicago

Jazzin' at the Shedd

Weekly jazz evening at Shedd Aquarium offering live music, drinks, and the aquarium's incredible marine exhibits.

Wednesday, June 10, 2026 5:00 PM · Shedd Aquarium, 1200 S Lake Shore Dr, Chicago

'90s Night at the Zoo – Adults Only Evening at Lincoln Park Zoo

Adults-only 90s-themed evening at Lincoln Park Zoo featuring live entertainment, food, drinks, and animal encounters.

Saturday, June 13, 2026 6:30 PM · Lincoln Park Zoo, Chicago

Marc E Bassy at City Winery Chicago

R&B/pop artist Marc E Bassy performs live at City Winery Chicago in an intimate dinner-and-show setting.

Sunday, June 14, 2026 7:30 PM · City Winery Chicago

Arts & Culture

Neue Deutsche Welle: Sounds of 1980s Germany Exhibit

Free exhibition at DANK Haus exploring West German punk, rock, and Neue Deutsche Welle music culture of the 1980s on both sides of the Berlin Wall.

Wednesday, June 10, 2026 10:00 AM · DANK Haus German American Cultural Center, 4740 N. Western Ave., Chicago

Lectures on Tap: A History of Crowd Control in the United States

Drinks-and-learning event in River North exploring the history of crowd control in the United States.

Wednesday, June 10, 2026 6:30 PM · River North, Chicago

The Jury Experience – Frankenstein on Trial at MCA

Immersive theatrical courtroom experience at MCA's Edlis Neeson Theater where the audience decides the fate of Frankenstein.

Sunday, June 14, 2026 · Edlis Neeson Theater – MCA, Chicago

Festivals & Special Events

Pride Drag Brunch starring Latrice Royale

Pride celebration drag brunch headlined by Latrice Royale of RuPaul's Drag Race All Stars at Chicago Improv.

Sunday, June 14, 2026 2:00 PM · Chicago Improv, Chicago

James Beard Restaurant and Chef Awards

The prestigious annual James Beard Awards ceremony celebrating the best chefs and restaurants in America, hosted in Chicago.

Monday, June 15, 2026 · Lyric Opera of Chicago, Chicago

Food & Drink

Monday Night Foodball: Windy City Burger Social Club at Thattu

The Reader's weekly chef pop-up at Thattu features Nas Masoud's smashed cheesesteak and hot dogs from Windy City Burger Social Club.

Monday, June 8, 2026 · Thattu, Chicago

Tacos and Tequila with Humanscale

Festive tacos and tequila event at Federales Tacos & Tequila in Fulton Market.

Monday, June 8, 2026 6:00 PM · Federales Tacos & Tequila - Fulton Market, Chicago