13 Things to Do in Chicago This Week · July 23–26, 2026

Music & Nightlife

Jess Hilarious at Chicago Improv

Viral comedian and actress Jess Hilarious brings her stand-up to the Chicago Improv for four shows over two nights.

Friday, July 24, 2026 · Chicago Improv, Chicago

Twin Tribes Night Club, Soft Vein, Wingtips

Riot Fest presents an intimate goth/darkwave lineup headlined by Twin Tribes at Concord Music Hall.

Saturday, July 25, 2026 Doors @ 7:00 PM · Concord Music Hall, Chicago

Festivals & Special Events

Randolph Street Market

Chicago's beloved outdoor vintage and antique market returns for a weekend of shopping, art, and community.

Saturday, July 25, 2026 · Chicago

Andersonville Summer Sidewalk Sale

One of Chicago's largest sidewalk sales stretches a full mile down Clark Street in Andersonville, with deals from local shops and a neighborhood festival atmosphere.

Saturday, July 25, 2026 · Clark Street, Andersonville, Chicago

Arts & Culture

Rodney Graham: Secondary Modern at Corbett vs. Dempsey

Ongoing exhibition featuring Rodney Graham's work at the respected West Loop gallery Corbett vs. Dempsey.

Saturday, July 25, 2026 · Corbett vs. Dempsey, 2156 W. Fulton St, Chicago

Kino, Kaffee und Kuchen

A German-language film screening with coffee and cake at the DANK Haus German American Cultural Center.

Saturday, July 25, 2026 10:30 AM · DANK Haus German American Cultural Center, 4740 N. Western Ave, Chicago

Food & Drink

An Idiot's Guide to Wine

A fun, interactive wine tasting experience at Chop Shop designed to demystify wine for curious drinkers.

Saturday, July 25, 2026 · Chop Shop, Chicago

Outdoors & Active

Read & Ride: Biking Tour of Malört with Josh Noel

An 11-mile biking tour through Chicago's neighborhoods tracing the curious history of Malört, led by the spirit's definitive biographer Josh Noel.

Friday, July 31, 2026 6:00 PM · Chicago

Free Events

Thalia Hall Free For All

Thalia Hall's summer building crawl with free programming across the main stage, Punch House, an outdoor hangout, and a special street stage.

Thursday, July 23, 2026 · Thalia Hall, Chicago

Wheeling Thursday Night Live

Southern Rock/Country singer-songwriter Lola Blu brings live outdoor music to the North Shore for a free evening concert.

Thursday, July 23, 2026 · Wheeling, Illinois

Millennium Park Summer Music Series

The city's beloved free outdoor concert series continues at the Jay Pritzker Pavilion in Millennium Park.

Thursday, July 23, 2026 6:30 PM · Jay Pritzker Pavilion, Millennium Park, Chicago

Sports

Savannah Bananas at Wrigley Field

The 'greatest show in sports' brings its trick shot-filled baseball entertainment series to Wrigley Field for a limited run.

Saturday, July 25, 2026 · Wrigley Field, Chicago

Family-Friendly

Savannah Bananas Free Fan Event at Chicago Dunkin' Locations

The Savannah Bananas host free fan meet-and-greet events at two Chicago-area Dunkin' locations ahead of their Wrigley Field series.

Friday, July 24, 2026 · Chicago Dunkin' locations