It’s your birthday. You shouldn’t have to plan your own celebration.

Another year deserves more than another dinner reservation. But getting everyone together comes with enough questions. Where are you going? What should you do? Where will everyone eat? Who’s making the reservations? Who’s coordinating transportation?

You shouldn’t have to figure it all out.

Raise A Glass takes it from there.

We’ll create a birthday experience that takes you beyond the ordinary and into Chicago’s hand-selected wine destinations, hidden gems, great food, and unexpected discoveries. You won’t know exactly where you’re going or what you’ll be tasting. That’s part of the fun.

Just bring your favorite people and come ready to celebrate. We’ll handle the route, reservations, transportation, wine, food, and all the details in between.

You celebrate another year. Your friends and family make the memories. And you get to enjoy your birthday instead of spending it managing the itinerary.

Perfect for milestone birthdays, intimate celebrations, birthday getaways, and anyone looking to celebrate another trip around the sun with great wine, great food, and even better company.

✨ Want to make the celebration even bigger? 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!