Every weekend friends and family are looking for new ways to create memories together. This is why our Friends and Family Wine Tour is the perfect way to have a night on the town filled with fun, laughter, and of course, wine and food!

Surround yourself with great company. Our team will handle all of the planning and details for you. We’ve got your back on this one! We have great relationships with some pretty cool wine bars and restaurants in the Chicago area. We’ll do all the work, make all the arrangements, and work with you to plan the schedule.

Our friendly wine tour guides will take you and your group to some of the hottest spots in the “Windy City” area to experience our unique wine and food scene! No worrying about reservations, who’s driving or “did I pick the right spot?” – we’ve got you covered here too.

Our tours give you an opportunity to celebrate with your friends and family, enjoy the moment as you create memories, and not have to worry about all of the details. You can leave that up to us!

We’re ready to help you create a day of fun that you’ll be talking about at your next holiday dinner!

✨ What’s Included

Your all-inclusive private Raise A Glass Tour in Chicago is curated for effortless luxury and unforgettable memories:

• 6 wine tastings at top local spots and hidden gems
• Charcuterie, appetizers, and dessert at three surprise locations
• Luxury transportation throughout the evening
• Dedicated tour escort ensuring a seamless experience at every stop
• Gratuity for servers included at each location
• Enjoy complimentary pickup and drop-off anywhere within the Chicago. Need a custom location outside the area? We’re happy to accommodate for an additional fee.

Join the Party — Public Tours

No group? No problem. Our public tours are open to everyone. Slide into a group of fellow wine lovers, foodies, and let us handle the rest. We’ll handle the surprise locations, the pairings, the pours, and the good vibes (limited dates available).

✨ Upgrade Your Private Tour to a Full Dinner Experience 🍷

Elevate your evening with an expanded wine tasting and a full multi-course dinner designed for a more memorable night out.

✨ What’s Included

• 9 curated wine tastings at top local spots and hidden gems
• Charcuterie & appetizers
• A multi-course dinner and dessert prepared by a Chef at three surprise locations
• Free pickup/drop-off within the Greater Chicago area.

Upgrade for $50 more per guest

Just add at checkout!