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Retro on Roscoe VIP Experience and Wine & Spirits Tasting
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Information

💰 Price List:

- VIP Weekend Experience (Friday, Saturday and Sunday): $75.00 per person
- VIP Experience (Nightly): $45.00 per person
*Add-On Wine & Spirits Tasting to any VIP Ticket for $22 per person!
- Wine & Spirits Tasting: $30.00 per person

đŸ—“ïžDates:
- VIP Experience: September 5th - September 7th
- Wine & Spirits Tasting: Saturday & Sunday, September 6th & 7th (Two sessions each day)

⏰Schedule:
- Friday: 5:00 PM to 10:00 PM
- Saturday: 12:00 PM to 10:00 PM
- Sunday: 12:00 PM to 8:00 PM
*For Wine & Spirits Tasting please note there are two sessions available!

📍2000 W Roscoe St., Chicago, IL 60618
đŸ‘€ This event is 21+ only

Your VIP tickets include:
- 2 drink tickets
- Private bar with specialty drinks 
- Private shaded seating area 
- Private bathrooms 
- Complimentary food bites from local restaurants

Your Wine & Spirits Tasting tickets include:
- Sample up to 8 different types of wine or spirits 
- Private shaded area to enjoy your samples
- Private bathrooms

*****Show your VIP or Tasting Tickets at the Gates for express entry!*****

About the event:

Whether you’re starting or ending your day with a tasting, it’s a great chance to sip something you’ve never tried before! 

Retro on Roscoe (Sept 5-7, 2025) – A Blast from the Past in the Heart of Chicago! 🎾🚗🎡

Get ready to time-travel at Retro on Roscoe, one of Chicago’s most beloved street festivals, happening September 5-7 in the charming Roscoe Village! This throwback extravaganza is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages.

Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.

Whether you’re a rock ‘n’ roll fanatic, a vintage lover, or just here for the good times, Retro on Roscoe is your ticket to a fun-filled weekend of music, memories, and retro magic! âœŒïžđŸŽ¶đŸš€
 

- All sales are final. No refunds or exchanges.

Special conditions

This event is 21+ only. You must be 21 to enter the VIP and Tasting areas.

Options

Options

Service
Amount
VIP Experience All Weekend: includes 2 drink tickets daily, private bar/bathrooms/seating, complimentary food bites from local restaurants
$75.00
Add on Wine & Spirits Tasting Saturday 12-2PM
$22.00
Add on Wine & Spirits Tasting Saturday 3-4:30PM
$22.00
Add on Wine & Spirits Tasting Sunday 12-2PM
$22.00
Add on Wine & Spirits Tasting Sunday 3-4:30PM
$22.00
VIP Experience Friday 5-10PM: includes 2 drink tickets, private bar/bathrooms/seating, complimentary food bites from local restaurants
$45.00
VIP Experience Saturday Noon-10PM: includes 2 drink tickets, private bar/bathrooms/seating, complimentary food bites from local restaurants
$45.00
Add on Wine and Spirits Tasting Saturday 12-2PM
$22.00
Add on Wine and Spirits Tasting Saturday 3-4:30PM
$22.00
VIP Experience Sunday Noon-10PM: includes 2 drink tickets, private bar/bathrooms/seating, complimentary food bites from local restaurants
$45.00
Add on Wine and Spirits Tasting Sunday 12-2PM
$22.00
Add on Wine and Spirits Tasting Sunday 3-4:30PM
$22.00
Wine & Spirits Tasting Saturday 12-2PM: includes samples of up to 8 different types of wine or spirits, private shaded seating and bathrooms
$30.00
Wine & Spirits Tasting Saturday 3-4:30PM: includes samples of up to 8 different types of wine or spirits, private shaded seating and bathrooms
$30.00
Wine & Spirits Tasting Sunday 12-2PM: includes samples of up to 8 different types of wine or spirits, private shaded seating and bathrooms
$30.00
Wine & Spirits Tasting Sunday 3-4:30PM: includes samples of up to 8 different types of wine or spirits, private shaded seating and bathrooms
$30.00
Register

Contacts

Email address
roscoevillageneighbors@gmail.com
Phone
+1 630-708-7244

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