Remember: tequila shots OR mint juleps, but not both.
Every few years, the stars align and two of the biggest spring party holidays, Cinco de Mayo and the Kentucky Derby, fall on the same weekend. It's possible to squeeze in both festivities if you plan ahead. Check out these five spots offering special events for the occasion—and make sure not to mix too many mint juleps and tequila shots. firstname.lastname@example.org | @redeyeeatdrink
Cinco de Derby at Roots Handmade Pizza
1924 W. Chicago Ave. 773-645-4949
This West Town pizzeria and sports bar offers Cinco de Mayo and derby specials Saturday and Sunday, including Woodford Reserve bourbon shots ($4) and mint juleps ($5), Cazadores tequila shots ($4) and locally brewed 5 Rabbit Latin-style beers ($4), plus 20 percent off barbecued pulled pork pizzas and taco pizzas both days. Fifteen TVs will broadcast the derby (5:25 p.m. Saturday) with sound so you can catch every hoofbeat of the blink-and-you'll-miss-it race.
Derby Day Crawl at Old Town Social
455 W. North Ave. 312-266-2277
Wake up, don your seersucker and start celebrating at Old Town Social beginning at 10:30 a.m. Saturday. Order a la carte brunch dishes and cocktails such as Pimm's cups and mint juleps, then catch the race on 23 TVs with sound. Post-race, hop the free trolley to swank RM Champagne Salon (116 N. Green St.) to round out the night with bubbles. Prizes will be awarded for best seersucker and best hat.
Derby Days Street Fest at Joe's Bar
940 W. Weed St. 312-337-3486
Weed Street channels Churchill Downs on Saturday from noon to 8 p.m., when the block surrounding Joe's will be closed off to accommodate race viewing on a jumbo screen, plus games such as bags and horseshoes. Since it's also an off-track betting facility, you can throw down your money if you think you've got your eye on the winning thoroughbred. Munch on snacks from food tents courtesy of nearby Whole Foods, then sip beer ($6) or mint julep ($7) specials and jam to the musical stylings of country band SaddleBrook.
The Kentucky Derby Comes to American Junkie
15 W. Illinois St. 312-239-0995
Doors open at 3 p.m. Saturday for the party at this sprawling, six-week-old River North bar and restaurant, which features a retractable roof and plenty of TVs to watch the race. Specials include an $8 Woodford Reserve mint julep and the option to purchase a commemorative cocktail cup ($50), with partial proceeds benefiting Paws Chicago. Come dressed to impress—prizes will be awarded for the best-dressed male and female. RSVP: RSVP@americanjunkie.com
Cinco de Mayo specials at Takito Kitchen
2013 W. Division St. 773-687-9620
Three dollars goes a long way Sunday at this new modern Mexican spot. Tequila shots and carnitas tacos made with pork shoulder, avocado and pickled ramps each set you back just $3, plus additional specials include the pozole verde soup ($5) and the Ruibarbo ($10), a El Jimador reposado tequila cocktail with flavors of rhubarb and yuzu. Noon-7 p.m.
See even more Cinco de Mayo and Kentucky derby party picks at chicago.metromix.com
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