photo: courtesy of kentucky derby
Come 5:24 p.m. local time this Saturday, May 4, all bets are off as the Kentucky Derby gets started. By that time, you should be wearing an ostentatious hat, enjoying (not your first) bourbon cocktail, and still hoping you'll win big on a bet.
Here are the best places in Chicago to experience the two most exciting minutes in sports. When the viewing parties end and the race is over, they'll be ready to help if that big bet didn't pan out—would another mint julep do?
Maria's Packaged Goods & Community Bar
Watch the Run for the Roses with a mint julep in hand—and no cover charge—at Maria’s (960 W. 31st St., 773-890-0588, starting at 12 p.m.). Or try the Jim Jam—a blend of Cabin Still bourbon, Averna Amano, and raspberry jam. We'll take Maria’s word that they know what they're doing with that cocktail.
Neighborhood: Gold Coast
Bring your most extravagant derby hat to the Chicago q (1160 N. Dearborn St., 312-642-1160, 3 p.m.–6 p.m.) viewing party for a chance to win a $100 gift card and basket of the restaurant’s house-made sauces, rubs, and pickles. Tickets are $42 and include an all-you-can-eat buffet from Chicago q chef Lee Ann Whippen. While you enjoy Kentucky-themed dishes, like bacon cheddar hushpuppies, pulled pork sliders, and a bread pudding with a q Bourbon caramel glaze, place $5 bets and compete for the grand prize, also a $100 gift card and basket. All proceeds go to Ronald McDonald House Charities.
Kit Kat Lounge
Kit Kat (3700 N. Halsted St., 773-525-1111, 11 a.m.–4 p.m.) may steal the Kentucky Derby’s thunder when the lounge unveils its newly redesigned patio. It’s the perfect place to enjoy a $6.50 mint julep and the “divalicious brunch,” which is available a la carte or a prix fix menu for $25. Of course, the afternoon wouldn’t be complete without a hat contest. The first-place winner will receive a $100 cash prize while the second-place winner will score a gift bag from Russian Standard Vodka worth $100.
Weather Mark Tavern
Neighborhood: South Loop
Weather Mark Tavern (1503 S. Michigan Ave., 312-588-0230, starting at 10:30 a.m.) departs from its usual nautical-themed concept for a day of Southern comfort, $7 mint juleps, and more giant hats, the best of which will win a prize. There’s no cover—that's more money you can bet.
Brownstone Tavern & Grill
Neighborhood: North Center
Not sure what creole cooking has to do with the derby, but when there’s crawfish involved, who cares? Brownstone Tavern (3937 N. Lincoln Ave., 773-528-3700, opens at 11 a.m.) flew in 1,000 pounds of crawfish from New Orleans, and the $30 all-you-can-eat crawfish buffet—complete with cornbread, gumbo, red beans, and rice—is a belt-loosening must. Besides no cover charge, there’s a chance to win a $500 grand prize if you correctly guess the derby’s winning horse. Smaller prizes awarded for skillfully predicating earlier races include restaurant gift cards and Maker’s Mark whiskey gift baskets.
The 10-Bar Bourbon-O-Rama
Neighborhood: Lincoln Park
If you really want to celebrate the derby this Saturday, start at the Lion’s Head Pub (2251 N. Lincoln. Ave., 773-348-5100, 12 p.m.–6 p.m.) for the Derby de Mayo pub crawl. It’s 10 bars in six hours for $17–$25. Tickets include three drink tickets (for Corona or Corona Light, so, um, bring some spare cash). And, yes, there will be a hat contest, and the winner will receive a Kentucky Derby hat from JG Hats.