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Love is a Funny Thing Podcast Live with October London & D'Lai
City Winery LLC
Love is a Funny Thing Podcast Live with October London & D'Lai

Love is a Funny Thing Podcast Live with October London & D'Lai

12/12/2026
Sat 6:00 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States
Sale starts soon

City Winery Chicago Presents Love is a Funny Thing Podcast Live with October London & D'Lai live on Saturday, December 12th at (opens in a new tab)6:00 PM! View all dates / times here(opens in a new tab)

Two powerhouse entertainers. One hilarious conversation about love. Grammy Award-winning R&B artist October London and comedian D'Lai bring Love is a Funny Thing Podcast Live to City Winery Chicago on December 12.

Known for his rich vocals and timeless soul sound, October London has earned multiple No. 1 hits on the Billboard R&B charts, including “Back to Your Place” and “Silent Treatment.” Discovered by Snoop Dogg and signed to Death Row Records, London has continued to build his reputation as a standout voice in modern R&B with releases including The Rebirth of Marvin, October Nights, and LOVE ME FOR ME.

Joining him is D'Lai, a nationally recognized comedian and master storyteller whose appearances include HBO's Def Comedy Jam, BET's ComicView, and Kevin Hart's Laugh Out Loud Network. His fearless humor, personal stories, and quick wit have earned him millions of devoted fans.

Together, October London and D'Lai explore the funny, messy, and relatable realities of love and relationships through music, comedy, and unfiltered conversation.Enjoy an unforgettable evening of laughter, soulful vibes, dinner, and wine at City Winery Chicago.

OPTIONAL ADD-ON:

Luv Is A Funny Thing Post-Show Meet & Greet Upgrade:

  • Exclusive meet & greet with D’Lai and October London
  • Personal photograph with D’Lai and October London
  • Exclusive Luv Is A Funny Thing VIP merchandise item
  • Official meet & greet laminate and lanyard; autographed by D’Lai and October London

*Ticket to event not included and is required to participate.*


🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.(opens in a new tab)


Reserve your preferred wine by filling out this form(opens in a new tab) and have a bottle waiting at your table when you arrive at your show. No more waiting for your first drink! We will save your wine preference and have a bottle at your table for all future shows. When you want to change your wine, come back to this form and update your preference.


2 Item Per Person Encouraged

🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.

The good news: we think you’ll love the food and wine just as much as the show.

🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile VIP+ members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.(opens in a new tab)

Love is a Funny Thing Podcast Live with October London & D'Lai
Main Stage, City Winery Chicago
Sale starts soon

12/12/2026
Sat 6:00 PM
Main Stage, City Winery Chicago
1200 W. Randolph St
Chicago 60607
United States