Where to Watch the Kentucky Derby in Chicago: Adalina’s Rose Lounge Brings Southern Charm to the Gold Coast

Run for the Roses, Stay for the Juleps.

Looking for the perfect spot to watch the Kentucky Derby in Chicago? Look no further than Adalina’s Rose Lounge, where elegance meets excitement for the most stylish two minutes in sports. On Saturday, May 3rd, we’re transforming our glamorous downstairs lounge into a Derby Day dream—complete with mint juleps, a Best Dressed Contest, and a chance to pick the winning horse number for a prize.

Whether you're a seasoned Derby enthusiast or just in it for the hats and cocktails, this is the ultimate Gold Coast destination to celebrate the tradition and thrill of race day. Catch the action on big screens in luxe comfort—all while sipping signature cocktails and soaking in the Southern charm.

Best Dressed Contest

Dust off your biggest hats, boldest bowties, and pastel power suits—our team will be scouting for the most stylish guest of the day.

Pick the Winning Horse

Everyone receives a number at the door. When the race begins, cheer on your lucky horse—if your number wins, you do too.

Classic Mint Juleps, Elevated

We’ll be shaking up this iconic Derby cocktail all day with our signature Adalina twist: fresh mint, crushed ice, and a generous pour of bourbon served in style.

Reservations are strongly encouraged—seating is limited.