Guide: Where to Celebrate Cinco de Mayo and the Kentucky Derby

Tomorrow is going to be a day of festivities celebrating Cinco de Mayo and the 138th running of the Kentucky Derby. Many places across the city will be having parties and specials to celebrate one or the other, or in some cases, both. So whether you want to sit around and drink margaritas all day or cheer for your favorite horse based on the name, there are plenty of options out there. Just don't forget to stay stylish and put on your best Derby hat and attire, there will be prizes to be won for Best Dressed.

1) Mercadito
Where: 108 W. Kinzie
What: Let Mercadito serve as your party central with specialty cocktails and a family-style sharing menu of guacamoles, salsas, tacos, sides and dessert to share at the table. Enjoy mariachi performances throughout the day and dancers and DJs at night. The sharing menu will be priced at $40 per person during the day and $50 after 9 p.m.
Call: 312-329-9555

2) Nacional 27
Where: 325 W. Huron
What: The festivities go down from 5 p.m. to 3 a.m. Half-priced tacos and empanadas in the lounge will be offered from 5 to 7 p.m., and a special Cinco de Mayo three-course prix fixe menu will include torta de carne, short rib “pozole,” baha-style sea bass and chico’s flan as options. The price of dinner is $29.95.
Call: 312-664-2727

3) Schoolyard, Kirkwood, Crossing
Where: 3258 N. Southport, 2934 N. Sheffield, 2548 N. Southport
What: A Cinco de Derby pub crawl at the three bars. The crawl includes an all-you-can eat taco bar at each spot and Coronas and Avion margaritas, as well as transportation between locations. Tickets are $20 in advance online.
Call: 773-528-8226, 773-770-0700, 773-327-4900

4) Brownstone
Where: 3937 N. Lincoln
What: Put on your most stylish derby hat and watch the Kentucky Derby at this crawfish boil party. $30 gets you an all-you-can-eat crawfish buffet as well as gumbo and red beans & rice. Other specials include $5 Maker’s Mark Mint Juleps and Saratoga Sunrises.
Call: 773-528-3700

5) Rockit Burger Bar
Where: 3700 N. Clark
What: Saddle up for a Kentucky Derby celebration from 3 p.m. to 6 p.m. with themed Derby drinks and bites. Tickets are $25 online and benefit the University of Chicago Kovler Diabetes Center.
Call: 773-645-4400

6) Cantina Laredo
Where: 508 N. State
What: White Sox fans can enjoy a pre-game radio broadcast as 670 The Score will be on site for the game. At 3 p.m., the Chicago Mambo All-Stars will fill the air with their songs until 11 p.m. No party is complete without a special cocktail and the refreshing “Cinco Mas ‘Rita” ($5) will keep the party going.
Call: 312-955-0014

7) Café 28
Where: 1806 W. Irving Park
What: Stop in for a special bar menu including pork belly tacos al pastor, tostaditas de carnitas and ceviche de mariscos con leche de tigre featuring shrimp and whitefish. Classic Mexican cocktails will also be available such as the Michelada.
Call: 773-528-2883

8) Barrelhouse Flat
Where: 2624 N. Lincoln
What: Nothing says the Kentucky Derby like some whiskey cocktails. Enjoy the classic derby drink, the Mint Julep, prepared shaken with bonded bourbon, mint and demerara syrup or the Old Fashioned, combining bonded bourbon with demerara syrup and orange & angostura bitters. All cocktails are $11.
Call: 773-857-0421

9) The Southern
Where: 1840 W. North
What: Celebrate Derby Day with an all-day celebration. Come in for brunch at 11 a.m. and enjoy Mint Juleps, $3 Tecate bottles and $3 shots of Heaven Hill Deluxe Bourbon. Seating begins at 3 p.m. and ends at 6 p.m. Tickets can be purchased online.
Call: 773-342-1840

10) Moonshine
Where: 1824 W. Division
What: An all-day Cinco de Moonshine event featuring the legendary taco bar outside, Mint Julep and margarita specials, live mariachi players from 6 p.m. to 8 p.m., $5 Moonshine crafted beers and DJs spinning Latin-inspired beats.
Call: 773-862-8686

11) Derby
Where: 1224 W. Webster
What: What better place to watch the Derby than at this aptly named spot. The Derby for The Derby event includes a lunch buffest, Mint Juleps, Bloody Marys, mimosas, beers, contests for best dressed and best derby hats and more. Tickets are $75 and can be purchased online.
Call: 773-248-0900

12) Carnivale
Where: 702 W. Fulton
What: Feast on some Cinco de Mayo specials that include squash blossom soup, crispy soft shell crabs, whole fried fish Veracruzana style and cochinita pibil whole roasted suckling pig.
Call: 312-850-5005

13) Cactus Bar & Grill
Where: 404 S. Wells
What: The party starts on May 4 with $4 Pacifico drafts, $20 Corona buckets and $5 margaritas. In addition, mini tostadas, spicy chicken quesadillas and housemade salsa and guacamole will keep the fiesta going all through Cinco de Mayo alongside DJs spinning festive music.
Call: 312-922-3830

14) The Pony
Where: 1638 W. Belmont
What: Cheer on your horse with $5 Mint Juleps, $4 Jim Bean & Red Stag shots and a $10 fried chicken platter. Win cash prizes from the best dressed and best hats contests as well a chance to score a free trip to the Equestrian Connection stables. A trolley crawl between The Pony, Lottie’s Pub and Frontier will also be taking place.
Call: 773-828-5055

15) Cafe Con Leche
Where: 2714 N. Milwaukee
What: $5 margaritas all weekend long and enjoy brunch with a live mariachi band from 11:30 a.m. to 1 p.m., and then again later that night from 10 to 11:30 p.m.
Call: 773-289-4274

16) Old Town Social
Where: 455 W. North Ave.
What: Come dressed to impress in your best Derby gear (hats and seersucker suits, y'all) for a chance at winning at $250 gift card. Other reasons to hit OTS' Derby Day? Jared Van Camp's patio pig roast, Mint Juleps, Pimm's Cups and 23 flat screens to watch the big race.
Call: 312-266-2277

Eater Chicago contributor Jeffy Mai contributed this article.