Where to Celebrate Cinco de Mayo in Chicago

By Michigan Avenue | April 30, 2019 | Food & Drink

From top-notch tippling to mouth-watering menus and more, these Windy City spots have your Cinco de Mayo plans all mapped out.

Barrio photo by Lindsey Simon/DineAmic Group.

The Katsuji Tanabe-helmed hotspot isn’t waiting for Sunday to arrive to embrace the revelry, kicking off the celebration early on Friday with three days of specials. Temptations include specially priced Don Julio shots ($6, May 3, 3PM-6PM), as well as weekend-long 1800 Tequila Margaritas ($10) and whopping 88-ounce margarita towers ($75). Prefer to sip suds? For $40, a dozen-can beer bucket of Corona, Tecate, Corona Light or Modelo satisfies—and begs to be paired with a toothsome guacamole flight ($16). May 3-May 5, 65 W. Kinzie St., 312.940.9900

Traveling might not be in the cards, but with Latin American dance tunes from DJ Bumbac Joe, half-priced large format libations and international eats like Spanish tortilla and duck egg shakshuka, the West Town see-and-be-seen spot whisks you away during a "Flight to Oaxaca" brunch, the latest installment of the restaurant's JETSET series. May 5, 1604 W. Chicago Ave., 312.929.4945

How’s this for a mixology treat? To toast the James Beard Awards weekend, World’s 50 Best Bars honoree La Factoría of Puerto Rico sets up shop in Chicago with a pop-up cocktail menu takeover at Broken Shaker. While there, nibble Puerto Rican-influenced bites from 27 Restaurant & Bar toque Jimmy Lebrón while grooving to sounds by DJs Dave Mata, King Tony and Daniel Villarreal-Carrillo. May 5, 8PM-2AM, 19 E. Ohio St., 312.940.3699

Punch Bowl Social
From karaoke and bowling to arcade games and more, action abounds at the sprawling Fulton Market funhouse—but with their El Macho cocktail (featuring Sauza Blue Reposado tequila) exclusively priced at $5, count on plenty of action to be barside all day long. May 5, 310 N. Green St., 312.809.9551

Old Town Pour House
The Wells Street haunt partners with Chicago Sport and Social Club for a special Cinco de Mayo brunch buffet, touting chilaquiles, taquitos and a bounty of morning staples, as well as bottomless Bloody Marys, Coronas and other tipples. Tickets available here, May 5, 11AM-2PM, 1419 N. Wells St., 312.477.2800

Tallboy Taco
Come for the dizzying selection of tacos (hello, veggie avocado) and stay for the drink deals, including Spicy Mami margaritas ($12) and Casamigos margaritas ($10). Five flavors of sangria is pretty enticing, too. May 5, 325 W. Huron St., 312.488.4917

The Underground
The late-night institution kicks off the weekend with the latest edition of its Art, Culture and Entertainment series with a Friday night art show and Tequila Avión tasting spotlighting works by CZR PRZ, Claraboyaaa and other local Mexican-American creatives (May 3, 10PM-12AM). Want to continue the revelry? Return the next afternoon for the club’s Cuatro de Mayo bash (May 4, 2:30PM-6PM & 10PM-5AM). 56 W. Illinois St., 312.644.7600

VU Rooftop Bar
The sky-high South Loop newcomer links with Tequila Avión for a trio of custom concoctions: the 44 Smash ($44), the Tequila Avión Silver-driven Mexican Firing Squad ($16) and the Spiced Pear Margarita made with Tequila Avión Reposado ($16). May 2-May 5, 133 E. Cermak Road, 312.528.0191

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