Our Small Group Wine Tours are perfect for those who are looking for something new, fun, exciting and all-inclusive to do with their favorite people! Invite a few others and all of you will be treated to a fun and relaxing private VIP experience! You’ll eat and drink wine together and enjoy each other’s company while we chauffeur you around the city in luxury transportation to some of the hottest wine and food spots the “Windy City” has to offer!

You and the people you invite will get a private wine tour around downtown and the Chicago area. Our goal is to give you an all-inclusive experience and opportunity to sample wines, create memories together, enjoy a night on the town, and end it hanging out at some of the hottest spots our city has to offer!

What’s Included on Every Tour:

• 6 curated wine tastings from celebrated global regions and local vineyards
• Charcuterie & appetizers
• Chef-prepared entrees
• Dessert for those “guilty pleasures” because the night should end on a sweet note
• Luxury Mercedes Sprinter transportation throughout the entire tour
• Free pickup & drop-off within the city (additional charge may be applied for locations outside the area)
• Dedicated expert tour guide for the full experience
• Gratuity for servers included at every location, so no awkward math at the end
• Bottled water throughout the tour
• A bottle of wine served in the Sprinter between stops
• Approximately 4 hours of immersive experience

Enhance Your Experience

Take your private tour from unforgettable to once-in-a-lifetime. Add any of these upgrades when booking:

Celebration Upgrade – Custom signage (Happy Birthday, Bride to Be, etc.), reserved premium seating where possible, champagne toast on arrival

Premium Wine Upgrade – Reserve wine experience — upgraded wines at two stops with higher-end and reserve selections

Signature Dining Experience – Chef-selected premium entree, reserve wine upgrade, and possible upgraded venue experience when available

Captured Experience – Professional photographer for key moments throughout the tour, edited photo gallery delivered post-tour

VIP All-Access Experience – Includes Reserve Wine Upgrade + Signature Dining Experience + Celebration Experience + priority flow & seating — the ultimate evening

Just add at checkout!