Our Amazing, Massive, What to Do On Cinco De Derby List

Napoleon III encourages you to drink responsibly.
Napoleon III encourages you to drink responsibly.

Honestly, we swear that the phrase “Cinco de Derby” had never existed in human history, but the coincidence of the Kentucky Derby and Cinco de Mayo both being on, uh, the cinco of Mayo led to an astonishing number of press releases containing the phrase (we also got one Derby de Mayo). Anyway, the prospect of horseracing and Mexican independence from Napoleon III seems to have led to a powerful thirst, and here are some specials we heard about for this weekend, broken up by rough area of town.


Hub 51: $4 Coronas, $6 Prickly Pear Margaritas, $8 guacamole, and it says “weather permitting, HUB 51’s patio will be rocking and once again debuting its signature Taco Cart,” which stopped us for a second till we realized that it’s debuting for this season, and that’s how you can debut more than once.

Moe’s Cantina River North: live music by the Sones de Mexico Ensemble Chicago, a Grammy-nominated folk ensemble featuring four-part harmonies and 25 instruments. The Dos Equis Girls will also be on hand handing out Dos Equis gear, and there will be $6 Dos Equis and $6 Red Pig Mexican Ale bottles.

Mercadito will mark the winning of independence in Puebla with a cooking demo of mole poblano and other Mexican foods, and a $40 per person all-day party including family-style platters of food ($50 after 9 p.m.), cocktails, mariachis and more.

Rockit Bar & Grill downtown will feature specials like chicken tortilla soup, blackened chicken quesadillas and a Mexican burger all week, and a whole Kentucky-Mexi party during Derby time. And The Underground is offering Cinco de Mayo margarita kits and margaritas made tableside.

• State and Lake Tavern: $1 tacos, $5 margaritas, $5 mint juleps.

• If just horseracing and Mexico isn’t enough, Cantina Laredo adds announcers from 670 The Score talking baseball before the White Sox game, followed by the Mambo All-Stars playing music at 3, and $5 margaritas.

Foodlife: $5 taco platter.

Zocalo: a festive Mexican brunch starting at 11:30, local Mexi-fusion band Fandanguero at 6:30 pm, dj’s into the night.

• Lastly, why wait till Saturday? Cactus Bar and Grill celebrates Cuatro de Mayo starting at 4 pm today, with $4 Pacifico drafts, $5 12-ounce margaritas, $5 Patron Silver shots, and $20 Mexican buckets (Corona/Corona Light), plus a d.j. and staff in costume.


Barrio Urban Taqueria: also musicians, plus an all-day fiesta with tequila specials.

• Rockit Burger Bar (the Wrigleyville one) will have a benefit Derby Day party for the U of C Kovler Diabetes Center; it’s $25 and Derby attire is encouraged. Get tickets here.

Brownstone finds a spot halfway in between Kentucky and Mexico, and has a crawfish boil ($30, all you can eat). Gaslight offers a Derby Day Whiskey Brunch, five courses, $45, tickets sold here. While $20 here gets you a ticket for a pub crawl including three Lakeview spots, Schoolyard, Kirkwood and Crossing.

Taco Joint: a special “taco del dia,” chicken confit with mole poblano and green poblano rice, garnished with crispy plantain strips. $5 Tecates with a shot of Jimador.


The Fifty/50 helpfully divides its specials by event so you can tell them apart; celebrate the Derby with $6 Woodford Reserve bourbon shots and $7 Woodford Reserve mint juleps, or celebrate Cinco de Mayo with $6 Cazadores tequila shots, $6 Cazadores margaritas, or $20 5-bottle Corona buckets. And the patron with the best mustache wins a party for him and ten of his friends at a future date. While Roots Handmade Pizza, from the same owners, has almost the same specials— same Woodford Reserve ones, but $3 tequila shots, $3 beers from 5 Rabbit, the “nation’s first Latin craft brewery,” and 20% off all Roots’ signature taco pizzas (dine-in only).

Moonshine seems to have everything but a bear fight planned: mariachis, pinata contests, DJs after dark, mint julep and margarita specials, and most of all their “legendary once-a-year Taco Bar featuring: outside grills blazing with fresh marinated skirt steak and chicken, a selection of tortillas & fixings, and unique hot sauces ($2 per taco).”

• This is just crazy: Smoke Daddy will fill a pinata with barbecue.

• Dunlay’s on Clark: $2.50 Horchata (have it spiked for $2), $3 Pacifico, $5 Hand Crafted Margaritas, $6 Raspberry Margaritas. Food Specials: $9 Dunlays House Guacamole, $12 Fish Tacos.

The Anthem: $8 margaritas and mint juleps, $4 Kentucky Hot Brown sliders, $3 pork belly tacos, Housemade Doritos free w/Tecate bucket purchase.

Tuman’s Tap & Grill and Mac’s American Pub: each featuring $5 Maker’s Mark, $5 mint juleps, $5 stagecoach fries (topped with melted Cheddar and mozzarella-ranch dressing— we worked a mozzarella ranch once in Italy), and an $8 Old Kentucky Hot Brown Sandwich.


• Tokio Pub at Woodfield in Schaumburg kicks off late night Saturdays with $1 tacos until 11 p.m., and lots of other cross-cultural fun like karaoke and $3 yuzu margaritas (also strawberry and pomegranate).

• Porter’s Pub in Elgin: $5 Mint Juleps, $2.50 Corona and Corona Lights, $5.25 Margaritas and $5.25 Tequila Specials. Food specials include a $10.95 Kentucky Hot Brown as well as a complimentary taco bar.

• Femme du Coupe: Also offering margarita kits is this “bespoke cocktails and bar styling” site, who will deliver a 20-margarita-kit for $40, made within minutes before your party for the peak of freshness. (The law being what it is, you have to buy and add the tequila on your own.) Read more about it all at her blog here.

Our Amazing, Massive, What to Do On Cinco De Derby List