Cinco de Mayo Guide, 2018 to Dining and Drinking

One of the liveliest and most colorful food- and drink-filled holidays of the year is almost here, and all over Chicago, restaurants and bars are gearing up to celebrate Cinco de Mayo. From cocktail specials to full-blown parties, here’s where to toast the Mexican-inspired holiday in style. 


Tuco & Blondie
Tuco & Blondie

Libertad: This Skokie staple is an ideal spot for Latin and Mexican flavors any time of year, but especially on Cinco de Mayo, when the kitchen busts out specials like pork ribs with morita-guajillo-pasilla adobo and nopales. To drink, they’ll have shots of Cimarron Blanco y Reposado, and $5 cans of 21st Amendment “El Sully” Mexican lager. 

Cantina Laredo: The three “M’s” are all represented at Cantina Laredo’s Cindo de Mayo shindig: music, margaritas and Mexican beers. From 11:30 a.m. until 11:00 p.m., the River North restaurant will augment its regular festive menu with three special “Fiesta Flip” cocktails, along with $3 Mexican beers like Dos XX Lager, Tecate and Modelo Negra. The cocktails on offer include the 3 G’s Please, made with tequila, fresh lemon juice, simple syrup, orange bitters and muddled strawberries topped with a tequila strawberry float. Then there’s the luscious Sunshine Margarita, which has 1800 Silver tequila, Grand Marnier, agave nectar and fresh orange, lemon and lime juices, plus a Grand Marnier-lemon float. To add a little pizzazz, DJ Matt Rochford will be spinning Mexican tunes from noon until 9:00 p.m. 

Tuco & Blondie: Tacos and margarita Jell-O shots are on hand at Tuco & Blondie’s holiday celebration this year. Come May 5, the Lakeview restaurant will be serving $3 steak tacos from the patio’s charcoal grill, plus margarita Jell-O shots. The restaurant is open from 10:00 a.m. until midnight. 

Lady Gregory's Old Town: Since Cinco de Mayo falls on the same day as the Kentucky Derby, another popular day for drinking and revelry, Lady Gregory’s Old Town outpost is doubling down with doubly festive “Cindo de Derby” specials. Drinks for the day include the Cinco Paloma made with tequila and Stiegl Radler, the Nube Cinco with tequila, soda and mint, and a Derby Pie Shot, which tastes curiously like pecan pie. For those who really want to crank things up a notch, there’s the Cinco de Derby Sweet Tea, a holiday mashup with tequila, sweet iced tea and mint. All drinks will be $10 and the shot is $6 for the day. 

Split-Rail: Another restaurant combining the two celebrations into one conveniently boozy package, Split-Rail is offering both pitchers of margaritas and mint juleps for $40, each serving up to eight people. There will also be food specials like nachos and pimento cheese and Benedictine dip. 

The Pony Inn: Two words: “salsa cook-off.” One fun way to mark Cinco de Mayo is with a zesty party at this Lakeview bar, which takes place on Friday, May 4, to kick off the weekend in style. The free event will include salsa tastings, plus specials like $3 tacos, $3.50 Dos Equis, and $5 Dobel. For those who would like to enter the salsa cook-off themselves, email