
The 151st Kentucky Derby takes place on Saturday, May 3 at Louisville’s Churchill Downs. Those in Chicago will still be able to catch the Run for the Roses at local bars and restaurants, where you can find food and drink specials. Be sure to arrive in style, because some spots will have contests for the best dressed.
I|O Godfrey
Found atop River North‘s Godfrey Hotel, I|O begins its annual party at noon, well in advance of the 5:57 p.m. post time. That gives plenty of time to sample bourbon tastings every half-hour between 1 and 4 p.m., food from the Derby Day menu and get a rocks glass dipped in Maker’s Mark’s red wax. Prizes will be handed out for Best Couple, Best Dressed and Best Hat. Men can enhance their style through a pop-up with the Tie Bar, who will sell the Derby’s official Laura Ashley collaboration and offer discounts to all guests. Purchase a raffle ticket based on the winning horse for a chance to win a customized suit. Reserve a ticket or a full table at Tock.
The Grillroom
In the Loop, The Grillroom starts its celebration a few days early. Starting Thursday, May, visitors can try an Old Forester mint julep ($14), Four Roses peach bourbon sour ($15) and an Oaks Lily with Tito’s ($13). The food specials consist of a trio of appetizers: BBQ pulled pork sliders ($15), deviled eggs & caviar ($22) and pimiento dip ($18). Even non-bettors can hit the “Trifecta” – all three dishes for $50.
Fatpour Tap Works
Fatpour Tap Works in Lincolnwood has planned a family-friendly event. From 4 – 7 p.m., kids can enjoy a petting zoo and pony rides, plus a hat-making station with prizes given to the best. Fatpour will have a pimiento cheese dip platter ($15.75) and a mint julep ($14). Former Bears receiver Tom Waddle, now of ESPN Chicago 1000 AM, will be on-hand from 4:30 – 6:30 p.m.

The Hampton Social
All Chicago-area Hampton Socials (River North, Streeterville, Skokie, Burr Ridge and South Barrington) will be showing the race. For Derby Day, they’ll offer a mint julep ($13) and H Rosé at half-price. A $100 gift card goes to the person with the best outfit. The party starts at 2 p.m. and reservations can be made at its website.
Bar La Rue
The floral decor of Bar La Rue makes it a fitting place to watch the Run for the Roses. Starting at 3 p.m., the French-inspired Fulton Market spot will have Derby-themed cocktails and food, plus a Best Dressed contest. Purchase a $20 ticket at Eventbrite.
The Wellsley
At The Wellsley in River North, guests can Southern-inspired food and cocktails, including mint juleps. The winner of the Best Dressed contests receives a $500 worth of gift cards for the Boka Restaurant Group, which includes many of Chicago’s most acclaimed restaurants. Tickets start at $60 and are available at Eventbrite.