Small group. Big experience. Zero planning required.

Getting three, four, or five people on the same page can be harder than it sounds. Everyone has a schedule, everyone has an opinion, and suddenly a simple day out turns into a group project.

Where are you going? What should you do? Where should you eat? Who’s making the reservations? And who’s responsible for figuring out what’s next?

That’s where Raise A Glass comes in.

We’ll create an experience that takes your group beyond the usual Chicago spots and into hand-selected wine destinations, hidden gems, great food, and unexpected discoveries. You’ll have a curated route without having to build one yourself. And there’s a little mystery along the way—you won’t know exactly where you’re headed or what you’ll be tasting until you arrive.

All you have to do is bring your people.

We’ll handle the route, reservations, transportation, wine, food, and all the details in between.

You get to explore Chicago without the planning. Discover places you may have never found on your own. And spend your time doing what you came for, enjoying great wine and even better company.

Perfect for small groups of 3–5 guests looking for a unique Chicago wine and dining experience without the hassle of planning every stop themselves.

✨ Want to make your experience even more memorable? Add the 3-Stop Signature Experience at checkout.

What’s Included on Every Tour

• Curated wine tastings at every stop
• Food pairings or full dinner, depending on the tour selected
• Luxury Mercedes Sprinter transportation
• Complimentary Pickup & drop-off within our service area
• Dedicated tour host
• Bottle of wine in the Sprinter
• Bottled water
• Gratuity at each stop

Enhance Your Experience

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

Champagne Toast – Start your experience with a celebratory champagne toast. Because some nights deserve a proper beginning.

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

Signature Dining Experience – Upgrade to our 3-stop Signature Dining Experience featuring appetizers and light bites, sharable small plates, and a decadent dessert experience all paired with wine throughout your tour.

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

VIP All-Access Experience – Take your Raise A Glass experience to the next level with our most elevated tour experience. Enjoy everything included in our 3-stop Signature Dining Experience, plus premium wine selections, a celebratory champagne toast, elevated dining, and exclusive VIP touches designed to make your day truly unforgettable.

Includes:

• 3-Stop Signature Dining Experience
• Premium Wine Upgrade
• Champagne Toast
• Elevated Dining Experience
• Exclusive VIP touches throughout your tour

Available for the entire group.

Just add at checkout!