Derby 2026 Events

Watch the Kentucky Derby 27 stories above the city at one of the top-rated rooftop bars in the world. ROOF on theWit puts a disco spin on Derby Day in the heart of the Loop with skyline views, cocktails, and a retractable roof that keeps the party going rain or shine. Dapper up and join the celebration.

Take your Derby Day to new heights on Joy District’s rooftop in River North. This multi-level hotspot turns the most exciting two minutes in sports into an all-afternoon affair with cityscape views, lush greenery, and the kind of scene that belongs on your Instagram. Dress up, show out, and get in on the action.

Perched above Hotel Lincoln with panoramic views of Lake Michigan and the Chicago skyline, The J. Parker is one of Lincoln Park’s most stunning indoor/outdoor settings. This is Derby Day with a rooftop view you won’t find anywhere else in the city. Pull up a seat, sip something cold, and watch the roses fly.

Old Town’s favorite rooftop playground goes full Kentucky Derby. Sitting above the legendary Second City, Utopian Tailgate brings a sprawling indoor/outdoor space, skyline views, and a party atmosphere built for a crowd that came to have a good time. Hats, horses, and a whole lot of fun.

Lincoln Park’s go-to sports destination goes all-in for Derby Day. With a retractable patio roof, wall-to-wall screens, and the kind of atmosphere that makes every race feel like a main event, Parlay (Lincoln Park) is where you want to be when those gates open on May 2nd. Dress up and throw down.

Hats on, cocktails up, races rolling. Paradise Park is turning Wicker Park into your Derby Day destination with a vibrant indoor/outdoor space, creative cocktails, fresh pizza, and every race on the big screens. Spring fashion, cold drinks, and one of Chicago’s favorite party spots doing what it does best.