Getting the group together should be the easy part. Finding an experience everyone will talk about is where we come in.

You know how it starts.

Someone throws out the idea: “We need to get everybody together.” Then the questions start. Where should we go? What will everyone enjoy? Who’s making the reservations? How are we getting around? And before long, the person who suggested the get-together is stuck doing all the planning.

Leave the planning to Raise A Glass.

We’ll take your group beyond the familiar and into Chicago’s hidden gems, hand-selected wine destinations, great food, and experiences you probably wouldn’t find on your own. We’ll create the route, choose the stops, and keep a little mystery along the way. You won’t know exactly where we’re headed or what’s waiting at the next stop. That’s what makes it an experience.

All you have to do is bring your favorite people and show up ready to explore. We’ll take care of the reservations, transportation, wine, food, and everything else along the way.

You explore Chicago. You discover new favorites. You laugh, connect, and make memories with the people who matter most.

Perfect for birthdays, family gatherings, friend getaways, date days, reunions, and groups looking to experience Chicago through great wine, food, and unexpected discoveries—all without having to plan the day yourself.

✨ Want to make the day even better? 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!