Things to Do in Chicago This Week (2025 Guide for Creatives, Locals & Visitors)

Whether you’re a local, a creative, or just visiting — this is your updated, no-fluff list of things to do in Chicago this week. No tourist traps. No pay-to-play events. Just curated experiences with real people, real energy, and real opportunities.

This guide stays fresh. Come back weekly for new updates on pop-ups, creative events, networking mixers, and 420-friendly gatherings worth your time. You can also check out our Pop-Up Shops Near Me guide if you’re planning ahead.

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🎨 Creative Events & Pop-Ups

• Outdoor Vendor Pop-Up (Wicker Park)
  
  📍 Milwaukee & Damen | Sat/Sun weekly | Free
  
  Rotating list of small brands, art prints, vintage, and creatives selling in the open air. Great for walking through or vending. If you’re looking for free vendor events, this one’s for you.
• CLVR LABs™ Micro-Market
  
  📍 Lincoln Park / West Loop (rotating) | Vendor-first setups
  
  Curated pop-ups with music, food, and high-conversion booths. Apply here to vend or check the live calendar.
• Late Night Art & Beats (South Side)
  
  📍 Promontory Basement | Friday night
  
  DJ sets + underground artists + 420-friendly vibes (no smoking on site). Great for meeting creatives without the clout games.

🛥️ Unique Networking Events

Not your standard panels and badge events. These are designed for community, business alignment, and creative collisions. If you’re looking to actually meet decision makers — these are the ones to watch.

• CLVR Yacht Salon (Summer of George)
  
  📍 River City Marina | Monthly | 21+
  
  Think yacht party meets founder mixer. Vibe is cannabis-aligned, not consumption-focused. Dress well, bring cards, build real connections. Book a seat.
• West Loop Founders Night
  
  📍 Private Loft | Invite or apply
  
  Investor-curated crowd. Culture meets capital. No influencers, just energy. Hosted by CLVR LABs™ & friends.

🌿 Cannabis-Aligned Events (Legal & Culture-First)

All events listed are 21+ and comply with Chicago law. No fake 420 “vibe” promos here — just culture-forward gatherings that are actually legal, actually smart, and actually happening soon. If you’re planning cannabis travel, check out our Bud and Breakfasts in Chicago guide.

• Cannabis & Creatives Market
  
  📍 West Loop | Monthly Series Launching Soon | Apply early
  
  Infused brands, small batch vendors, music, and real culture crossover. You’ll meet artists, not just stoners.
• CLVR LABs™ Education Series
  
  📍 River North | Fall 2025 | Free RSVP List Opens Soon
  
  Covering licensing, partnerships, and compliant scaling — for cannabis brands that want staying power, not just pop-up hype.

🆓 Free Things to Do This Week

• 🎧 Live DJ pop-up – Sunday at the Lakefront Skatepark
• 🖼️ Chicago Artists Pop-Up Gallery – Wednesday in Logan Square
• 🪩 Open Mic Night – Thursday at Recess Studios
• 🏙️ CLVR LABs™ Walkthrough – Vendor preview & meet the team (RSVP only)

Want more free events? Check out our full list of free things to do in Chicago today.

👉 View Our Events | Apply to Vend | Sponsor CLVR