February 19-22, 2026
What Happens at Paint the Town?
Eating, drinking, dancing, shopping. All the things one would expect from a world class city. From first rate museums and live entertainment to neighborhood clubs and historical attractions - Chicago has it all.
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The Paint the Town schedule has two group activities each day - a happy hour 'meet and greet', followed by a dinner/entertainment activity. The rest of the time is open for you to explore the city. Maybe a little shopping or a museum during the day. And, after dinner it might be a dance club or a quiet dive bar to chat with new friends.
Happy Hour
After freshening up from your daytime activities, we invite you to join us for drinks and a snack before we all head out for the evening activity. A casual atmosphere to chat about your day and make plans for after dinner shenanigans. We host a professional photographer - so you can get great pics in your fabulous evening outfit with friends.
Making Friends Before and After
Nothing solidifies a friendship more than hanging out in person - what Paint the Town is all about. But, before you arrive, you might want to know who else is attending. Get to know them a bit and possibly make plans for daytime excursions.
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Don't know what to do or where to go during unscheduled afternoons? Don't know about the best late night dance clubs? Once you register, we'll invite you to our private discord server where you can chat and make plans with other attendees.
We'll provide activity suggestions and promote self-organization into smaller groups to do activities that match your interests.
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When Paint the Town is over, the discord will remain open so you can keep in touch with all of the new friends you made during the memorable weekend.
Sample Schedule
Thursday
Lunch and Afternoon Activity
Unscheduled - use discord to make individual plans with other attendees.
Happy Hour
5-7pm - Location TBD
Dinner and Entertainment
7-10pm - Scheduled TBA
Late Night Activities
Unscheduled - use discord to make individual plans with other attendees.
Friday
Lunch and Afternoon Activity
Unscheduled - use discord to make individual plans with other attendees.
Happy Hour
5-7pm - Location TBD
Dinner and Entertainment
7-10pm - Scheduled TBA
Late Night Activities
Unscheduled - use discord to make individual plans with other attendees.
Saturday
Lunch and Afternoon Activity
Unscheduled - use discord to make individual plans with other attendees.
Group Photo
5pm - Location TBD
Happy Hour
5-7pm - Location TBD
Dinner and Entertainment
7-10pm - Scheduled TBA
Late Night Activities
Unscheduled - use discord to make individual plans with other attendees.
Sunday
Bye Bye Breakfast
10am - Scheduled TBD - Stop by for an end of the weekend breakfast before you head home.
Previous Dinner and Entertainment Activities
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Untitled Supper Club - Dinner and Live Music (link)
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Punch Bowl - Dinner and Games (link)
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The Comedy Bar - Standup and Chicago Pizza (link)
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Andy's Jazz Club - Dinner and Live Music (link)
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Newport Theater - Live Burlesque Show (link)
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Annoyance Theater - Live Comedy Show (link)
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Dinner and Dancing in Boystown (link) - Drew's, Wood, Mia Francesca and Bites are great dinner options