You’ve got enough to plan for the bride. The perfect bachelorette experience shouldn’t be another thing on your list.

The dress is picked. The guest list is together. The decorations are handled. And now someone has to figure out where everyone is going, what the bride will love, where you’re eating, and how you’re getting around Chicago.

That’s a lot of planning for one person.

Raise A Glass takes it from there.

We’ll take the bride and her favorite people beyond the typical bachelorette night and into Chicago’s hand-selected wine destinations, hidden gems, great food, and unexpected experiences. You won’t know exactly where you’re going or what you’ll be tasting. That’s part of the adventure.

Just bring the bride and her crew. We’ll handle the route, reservations, transportation, wine, food, and all the details in between.

You celebrate the bride. You laugh, explore, sip, and make memories together. And nobody has to spend the day checking the itinerary or figuring out what’s next.

Perfect for bachelorette parties looking for a unique Chicago experience that’s fun, elevated, and completely taken care of from the first stop to the last.

✨ 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!