Saturday, May 3
Swap your boots and flannels for floppy hats and sundresses on race day at this country restaurant and bar. The party begins with a commemorative glass giveaway for the first 100 mint juleps sold, and gallops on with traditional hot brown sandwiches stacked with hickory smoked turkey breast, served open-faced on Texas toast with white cheddar mornay sauce, tomatoes, and house-made bacon—and, of course, bourbon galore. 435 N. Clark St., 312-610-4200
Saturday, May 3
Arrive at Tavern On Rush dressed to really impress for its third annual Kentucky Derby Party, and you might just walk away with a free bottle of Dom Perignon suited for après-Derby imbibing. The Tavern will offer specially priced Maker’s Mark Mint Juleps all day long, as well as festive menu items like Crispy Churchill Fried Chicken Chopped Salad, a “Run for the Roses” potato chip basket, and Kentucky bourbon banana bread pudding courtesy of Executive Chef John Gatsos. 1031 N. Rush St., 312-664-9600
Enjoy exclusively priced oysters on Derby Day at RM Champagne Salon.
Saturday, May 3, starts at 1 p.m.
Spend Derby Day at West Loop’s always-glamorous RM Champagne Salon. House mint juleps and beer will be flowing, buck-a-shuck oysters will be served, and grand prizes for best seersucker looks and best hats will be awarded to those who flaunt their Churchill Downs best. 116 N. Green St., 312-243-1199
Ongoing; but perfect on Monday, May 5
Rise and shine on Cinco de Mayo for a Mexican-inspired breakfast or brunch packed with Chef Greg Ellis’ interpretations of popular dishes like chilaquiles with white corn tortilla chips, fire-roasted tomatillo salsa, sunny side-up farm-fresh eggs, queso fresco, and roasted Anaheim pepper aioli, with your choice of beef chorizo or roasted chicken. Wash your meal down and keep a case of the Mondays away with a citrusy tequila sunrise. 553 W. Diversey Pkwy., 773-234-2320
Saturday, May 3-Monday, May 5
Parched on Cinco de Mayo? Swing by this bustling Division St. watering hole for exclusively priced Cazadores Reposado Margaritas and a bucket of Coronitas to share with a few friends over house guacamole, nachos, and Fiesta burgers (since it is, after all, National Burger Month). 1932 W. Division St., 773-278-1919
HBFC’s well-lit patio is prime for Cinco de Mayo noshing.
Monday, May 5, 6 and 8:30 p.m.
Avondale’s premier chicken stop will host a Cinco de Mayo-inspired feast with two seatings (tickets on brownpapertickets.com). The $45 prix fixe meal includes 5 Rabbit Beer and a La Finca margarita, a plate overflowing with chips and salsa verde, pork belly chicharron sope, a green chile lamb tamale, and smoked chicken posole, plus a rhubarb horchata popsicle with feuilletine crunchies for dessert. 3361 N. Elston Ave., 773-478-4000