Best Pop Up Events in Chicago You Don’t Want to Miss This Winter 2026 | CLVR LABs™

Chicago stays busy in winter. Pop ups move indoors. Markets fill up. Artists and small brands meet new buyers. This is your guide.

This is not hype. It is the street report.

What Makes a Winter Pop Up Work

The best Chicago pop ups share three traits:

• Real fit with the crowd — right neighborhood, right time.
• Simple path to buy — clear price, fast checkout, QR ready.
• Multi format content — live, digital, and social in one plan.

Top Picks You Should Not Miss

• CLVR Sundays: Artist Showcase + Vendor Networking — a packed night by CLVR LABs™. Music, makers, and real connections.
  See dates or
  apply to vend.
• Indoor Maker Markets — warm rooms in Wicker Park and Logan Square. Great for first time vendors. Low setup stress.
• 420 Friendly Events — adult crowds with a calm vibe. Lifestyle brands do well here. Read our guide next.

How to Get Ready if You Are New

1. Pick one date from the events page.
2. Apply for a booth. Spaces start at $149 on the vendor form.
3. Keep your table neat. Use clear signs. Take mobile pay.
4. Collect emails. Post a recap. Follow up in two days.

Read Next

• How to Sell Out Your Vendor Booth Without Feeling Pushy
• 5 Mistakes Vendors Make That Kill Sales at Pop Ups
• 420 Friendly Events in Chicago That Actually Feel Classy

View Events
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Quick FAQ

How much is a booth?
Booths start at $149. Some categories vary.

How do I apply?
Use the vendor form linked above. We reply fast.

Where are the dates?
All live dates are on the events page.