1. Chicago Colors
The Chicago Pride Parade has attracted over a million LGBTQ+ community members and allies during each iteration in the last decade. It’s a good thing the parade spans from Uptown to Lincoln Park — it’s hard to fit that crowd in a single neighborhood. June 25. chicagopride.gopride.com
2. Happy as a Clam
Bluegrass music, the crackling of a fire pit, the smell of mussels and shrimp — it can only be the Guild Row Clambake. Each ticket comes with all-you-can-eat food, a welcome cocktail, and maybe even the lingering taste of New England once it’s over. June 23. exploretock.com
3. Lemonade Stand
2023 marks half a century of hip hop, but Lyrical Lemonade Summer Smash has more than 50 artists for the occasion. Kid Cudi, Future, and Playboi Carti headline, but hometown icons G Herbo and Lil Durk (as a guest) will also make an appearance. June 23–25. thesummersmash.com
4. Pride Performance
The Burr Ridge Art Fair is as diverse as it is expansive, with over 100 artists and works across a gamut of media. Enjoy on-site refreshments, live music, and the opportunity to create your own artwork at a live painting class, if inspiration strikes. June 24–25. amdurproductions.com
5. Jost with the Most
If you’re a Saturday Night Live fan, your calendar might need a weekend update. SNL cast member Colin Jost is set for two nights at the Chicago Theatre, the last leg of his 11-show tour. June 24–25. colinjost.com