City Cast Chicago
📆 Pride parties! Wiener Wars! Comedy!
June 23, 2025 · — Emmi Mack
Good morning! It’s finally officially summer — and if you’re anything like me, you want to soak up every minute of it. There’s so much happening around Chicago, so we’ve pulled together a list of the best events to help you plan your first full week of summer fun.
If you love seeing all of Chicago's best events in one place, join City Cast Chicago Neighbors. Our members get this curated events roundup every Monday — plus other great perks that help you feel even more connected to your city.
Here we go!
What To Do
Monday, June 23
- 🌳 Tree Identification Walking Tour | Archer Heights Branch | Archer Heights
- 🎵 Afrobeats on the beach | Pier 31 | Bronzeville
- 🙏 Faith is Funny: Comedy Writers on God and Religion | Studebaker Theater | Loop
- 🐕 “Homeward Bound” | Mary Bartelme Park | West Loop
- 🎤 James Blunt Back to Bedlam 20th Anniversary Tour | The Salt Shed | Goose Island
- 🤘Punks for Palestine | Nabala Cafe | Uptown
- 🎥 Field Notes Film Festival | Music Box Theatre | Lakeview
Tuesday, June 24
- 🍽️ Maria’s Patio Jam | Maria’s Packaged Goods & Community Bar | Bridgeport
- 💃🏻 On the Move | Palmisano Park | Bridgeport
- 🎤 FKA Twigs | Salt Shed | Goose Island
- 🏀 Sky vs. Sparks | Wintrust Arena | McCormick Square
- 🤣 Kyle Mooney | Metro | Wrigleyville
- 🏃♀️ Running Tour of “The Girls in 3-B” | Vuori | Loop
- 💪 Backyard Basics Fitness Club | Logan Square
Wednesday, June 25
- 😋 Flavors of Albany Park | Albany Park
- 🕺🏻 Club ZinZanni | Teatro ZinZanni | Loop
- 🏳️🌈 Werk: Chicago’s Premiere Queer Comedy Show | Lincoln Lodge | Logan Square
- 🎆 Bottomless Margaritas & Fireworks | Riverwalk
- 🎤 FKA Twigs | Salt Shed | Goose Island
- 📚 BUZZED WORDS: Adult Spelling Bee | Prost! | Lincoln Park
- 🏺 BYOB Beginner Pottery | Color Cocktail Factory | Pilsen
- 🏳️🌈 Lesbian Speed Dating | Tabu | West Loop
- 🎤 Comedy open mic | Free | 8 p.m. | Logan Square
Thursday, June 26
- ⚡️ “Lightning” | Gene Siskel Film Center | Loop
- 📖 Adult Book Discussion: “The Last Chance Library” | Harold Washington Library | Loop
- 🧱 Play at the Library: LEGO® and Giant Word Winder | Jefferson Park Branch | Jefferson Park
- 🏳️🌈 Out & Abt Pride: CHICAGO | Joy District | River North
- 🎭 “My Best Friend Is Black” | Lincoln Lodge | Logan Square
- ✍️ Writing Queer Tour | American Writers Museum | Loop
- 🖼️ Rosalyn Deutsche opening | The Art Institute of Chicago | Loop
- 💥 Quimby’s After Hours: Raging Opposum | Quimby’s | Wicker Park
Friday, June 27
- 🎥 "Hasik" Chicago Premiere | FACETS Film Forum | Lincoln Park
- 🖼️ Great Ideas of Humanity: Opening Reception | Design Museum of Chicago | Loop
- 🍺 Enmolada | is/was | Ravenswood
- 🔥 Third Coast Tattoo Show | Morgan MFG | Fulton Market
- ⚾️ Chicago White Sox vs. San Francisco Giants | Sox Park | Bridgeport
- 🎵 All of Us Chicago | Grant Park
- 🎶 The Roots | Ravinia Festival | Highland Park
- ✍️ Poems While You Wait & Leatherbound Lit Poetry | Leather Archives & Museum | Edgewater
- 🖼️ Seuil Chung: I See Ghosts opening | Lillstreet Art Center | Ravenswood
- 🏳️🌈 All White Yacht Gay Pride Kickoff | Anita Dee Yacht Charters | DuSable Harbor
Saturday, June 28
- 💥 CAKE: Chicago Alternative Comics Expo | The Irish American Heritage Center | Mayfair
- 🌭 Chicago Food Truck Festival | Motor Row District
- 🖼️ The Black Aura: A Weekend of Liberation and the Arts | The Kehrein Center For The Arts | Austin
- 🏳️🌈 Proud to Run: Pride Race 2025 | Montrose Grove 16 | Uptown
- 🌮 Meze Table | Electric Funeral | Bridgeport
- 🍹 Chicago Margarita Festival | South Loop
- 🔥 Third Coast Tattoo Show | Morgan MFG | Fulton Market
- 🎵 All of Us Chicago | Grant Park
- 🖼️ Art for the Sole 2 | Elephant Room Gallery | South Loop
- 🏳️🌈 Insomnia Exotic Night | Room43 | Kenwood
- 🥤 Red Cup Karaoke | The Promontory | Hyde Park
- 🏳️🌈 Black LGTQ+ Saturday Night Party | DS Tequila | Northalsted
Sunday, June 29
- 🏳️🌈 Chicago Pride Parade | Northalsted
- 🍽️ Sunday BBQ: Perilla | Sportsman’s | Ukrainian Village
- 🏳️🌈 Chicago Urban Pride Picnic | Jackson Park
- 🪅 Piñatta | is/was | Ravenswood
- 🏳️🌈 Pride in the Sky | The Promontory | Hyde Park
- 💥 CAKE: Chicago Alternative Comics Expo | The Irish American Heritage Center | Mayfair
- 🍹 Chicago Margarita Festival | South Loop
- 🔥 Third Coast Tattoo Show | Morgan MFG | Fulton Market
- 👀 Open Studio | Michael Bever Art Studio | Ravenswood
- 🏳️🌈 The Lesbian Social Club’s Pride After Party | Moe’s Cantina | Wrigleyville
Monday, June 30
- 🌭 Windy City Wiener Wars | Perilla Fare | West Loop
- 🎤 Tyler, The Creator with Lil Yachty and Paris Texas | United Center | Near West Side
- 📚 Book Club: “Tales of the City” | George Street Pub | Lincoln Park
- 🖼️ Holly Hughes | School of the Art Institute of Chicago | Loop
- 💪 Pop-up Workout | Cricket Hill | Lakeview
- ☕️ Café con Pilates | Waveland Picnic Field | Lincoln Park
- 🤣 Comedy at The Kennedy | Kennedy Rooftop | Wicker Park
- 🤘 Punk Rock Mondays | Delilah’s | Lincoln Park
- 🌅 Summer & Fall Afterwork Sunset Cruises on Lake Michigan | Anita Dee | DuSable Harbor
⚾️ Also: Don't forget to check out today's podcast all about 16-inch softball in Chicago.
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