Our Small Group Wine Tours are perfect for those who are looking for something new, fun, exciting and all-inclusive to do with their favorite people! Invite a few others and all of you will be treated to a fun and relaxing private VIP experience! You’ll eat and drink wine together and enjoy each other’s company while we chauffeur you around the city in luxury transportation to some of the hottest wine and food spots the “Windy City” has to offer!

You and the people you invite will get a private wine tour around downtown and the Chicago area. Our goal is to give you an all-inclusive experience and opportunity to sample wines, create memories together, enjoy a night on the town, and end it hanging out at some of the hottest spots our city has to offer!

✨ 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.

✨ Upgrade to the 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!