
About this Event
Gilded Summer Goodbye
With Dandy Wellington
IMSS is thrilled to welcome Dandy Wellington for a 3-day special event combining cocktails, conversations, concerts, and more!
Centered around the history of IMSS’s storied Lakefront mansion home, the weekend will feature music and dress from the gilded age through special museum tours, panel conversations about the vintage lifestyle, and performances blending the unique sounds of 1920's Chicago and Harlem Jazz.
Tickets:
Friday
7:00pm-11:00pm
- Cocktails & Chicago Jazz - $50
Saturday
3:00pm-5:00pm
- Vintage Lifestyle Panel - $25
7:00pm-11:00pm
- The Dandy Wellington Band, Early-Bird (Ends July 1st) - $100
- The Dandy Wellington Band, Presale - $125
- The Dandy Wellington Band, GA (at Door) - $150
Package & Addons:
Windy Weekend Package
- Early Bird - $150
- Presale - $175
Admission to Cocktails & Chicago Jazz, the Vintage Lifestyle Panel, and The Dandy Wellington Band
VIP Windy Weekend Package
- Early Bird (Ends July 1st) - $200
- Presale - $250
Admission to the VIP Sip n' Tour, Cocktails & Chicago Jazz, the Vintage Lifestyle Panel, and The Dandy Wellington Band
Lite Weekend Package
- Early Bird Early Bird (Ends July 1st) - $200 - $60
- Presale - $75
Admission to Cocktails & Chicago Jazz and the Vintage Lifestyle Panel
VIP Sip n' Tour Add-on
- $50
Add on admission to the VIP Sip n' Tour to any ticket!

:
For over 15 years, Dandy Wellington has captivated audiences and facilitated meaningful conversations from behind the microphone. Whether hosting corporate events for AirBnB and Connecticut Children’s Medical Center, moderating panel discussions on the RMs Queen Mary II, or conducting one-on-one interviews with Dita Von Teese and Paula Sutton at Goodwood Revival, Dandy brings an authentic and seasoned approach that fosters deep connections with guests and enhances the integrity of events.
As an emcee, Dandy Wellington has, since 2009, been the voice of corporate gatherings, weddings, vintage and variety events at breathtaking venues such as The Beaker Palm Beach, The Rainbow Room, The Beverly Hills Hotel, Grand Hotel Tremezzo in Lake Como, Italy and more. His clients include but are not limited to Elan Artists, The Plaza Hotel, The Great Gatsby Party, Scarlet Entertainment, The Galveston Historic Foundation, Prohibition Productions, Dances of Vice, The Champagne Riot, The 1940s Ball, and The Soapbox Presents.
As a panelist and interviewer, Dandy has engaged in discussions with academics, historians, stylists and influencers - including Shantrelle P. Lewis, Monica L. Miller, Ph.D., Douglas Jones, Ph.D., Justin J, Natty Adams, Jessica Kellgren-Fozard, Raissa Bretana, Quentin Thrash and Alphonso McClendon - at venues such as the National Museum of African Art, Smithsonian Institution; and the Fashion Institute of Technology
Friday
🕑: 05:00 PM - 06:30 PM
VIP Sip & Tour
Info: Guests are offered a specialty cocktail in an outdoor bar area before being led on a guided tour of 1524 N. Lake Shore’s History as a Historic Home.
🕑: 07:00 PM - 11:00 PM
Cocktails & Chicago Jazz
Info: Guests gather and mingle on the grand 2nd Floor of the Countiss Mansion, imbibing and enjoying light bites to the sounds of the Dandy Wellington Quintet blending together Chicago & Harlem Jazz.
Saturday
🕑: 03:00 PM - 05:00 PM
Vintage Lifestyle Panel
Info: Dandy Wellington is joined in conversation by other Vintage Lifestyle influencers from Chicago and the US, discussing Fashion, Style, and history, followed by Audience
Q & A
🕑: 07:00 AM - 11:00 PM
The Dandy Wellington Band
Info: Guests will enjoy the sound of the Dandy Wellington Ensemble, an 8-piece band specializing in harlem Jazz. Refreshments will be provided and small acts will offer entertainment during breaks in the music.
Event Venue & Nearby Stays
International Museum of Surgical Science, 1524 North Lake Shore Drive, Chicago, United States
USD 28.52 to USD 215.26