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Fri Oct 16 2026 at 08:00 pm to 11:00 pm UTC-05:00

Chicago R&B Sing A Long Paint & Sip:Sweetest Day Edition

  • Sonder Exchange · Chicago
  • From USD 131.74
The BalloonBestie Publisher / Host The BalloonBestie
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Chicago R&B  Sing A Long  Paint & Sip:Sweetest Day Edition Chicago, you know EVERY word! Grab your boo & sing, sip, paint and step your way through the ultimate grown & sexy Sweetest Day date night❤
About this Event

CHICAGO R&B SING-ALONG PAINT & SIP

SWEETEST DAY: CHICAGO EDITION ❤️

Friday, October 16, 2026 | 8–11PM📍 Sonders Exchange | 6534 S. Ashland Ave., Chicago🚗 FREE PARKING🎟️ Couples tickets starting at $125 | Early Bird $110

LADIES… BRING THAT MAN OUT. ❤️

Sweetest Day is coming, and instead of another dinner reservation, give him a night y’all can actually have FUN together.

Good food. Good drinks. Cigars. Chicago R&B. Stepping. Painting. And a room full of grown folks singing the songs we grew up on.

You pick the outfit. Grab your man. We’ll handle the date night.

PAINT. SIP. SING. STEP.

🎨 PAINT — Sit side-by-side and create your own pre-sketched canvases. Everything you need to paint is included—no artistic skills required.

🍸 SIP — 2 complimentary drink tickets per guest, plus a menu of themed signature cocktails available throughout the night.

🎤 SING — THIS is where the night gets good. We’re running through the greatest hits from Chicago R&B legends—slow jams, love songs, stepping records and those classics where everybody in the room knows what comes next.

And fellas… if she hands you that imaginary microphone, you better know your part. 😂

💃🏾 STEP — It wouldn’t be a Chicago grown-folks night without clearing the floor. Step with your lady, dance, sing and enjoy yourselves.

🍽️ EAT — Food vendors will be on-site, so there’s no need to make dinner reservations before you come. Food available for purchase.

💨 CIGAR LOUNGE — And yes, we thought about HIM too. Our outdoor cigar lounge gives the fellas—and anybody who enjoys a good cigar—a place to step outside, grab a cigar and catch a vibe. Cigars available for purchase.

🚗 FREE PARKING — Pull up, park and enjoy your night.

LADIES, THE SWEETEST DAY PLANS ARE ALREADY MADE.

Whether that’s your husband, boyfriend, fiancé, new boo 👀 or the man you’ve been dating and trying to figure out what to do with 😂 — bring him out.

Give him something better than another gift.

Give him a night with YOU.

🎨 Paint together.🍸 Have a couple drinks.🎤 Sing way too loud.💃🏾 Step a little.💨 Hit the cigar lounge.🍽️ Grab some food.❤️ And make a memory.

Friday, October 16 | 8–11PM Sonders Exchange | 6534 S. Ashland Ave., Chicago 35+ | Valid ID required🎟️ Couples tickets starting at $125 | Early Bird $110

Sweetest Day is for HIM. The experience is for BOTH of you.



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Event venue

Sonder Exchange, 6534 South Ashland Avenue, Chicago, United States

Tickets USD 131.74 to USD 355.77
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