From visiting the Paseo Boricua for a walk around Humboldt Park to the Wings of Mexico pop-up last year and every vibrant neighborhood event in between, Chicago is known for its celebrations, and as Cinco de Mayo approaches, we’re running you through the top ways to ring in Cinco de Mayo this year— whether you choose a rowdy bar crawl, a margarita fueled brunch or a block party.
Cinco de Mayo’s annual celebration always falls on the anniversary of Mexico’s victory over the French Empire in the Franco-Mexican War.
While it’s not actually a significant holiday in Mexico, the holiday has become an annual celebration of Mexican American culture in the U.S., often including parties, traditional foods, and drinking events.
Chicago, which often holds some of the largest Cinco de Mayo celebrations, has various events taking place throughout the city this year. We have a beautiful Latino community here in Chicago, and there are a host of events going on this weekend to celebrate the holiday.
In need of plans for Cinco de Mayo? Keep reading for a look at the upcoming celebrations.
1. Enjoy drinks and food at Pilsen Fest Cantina Crawl
Taking place later in the month on Saturday, May 20th, the Pilsen Fest Cantina Crawl lets you stroll down 18th Street, enjoying live music, bands, murals, and more along with an 8-stop cantina crawl including bars and restaurants in the area!
Going from 12 to 6 p.m. the annual celebration offers a complimentary drink from each location and explores Pilsen’s legacy for its diverse Latino/Mexican culture, using music, poetry, food, and more to promote community pride.
2. Attend A Peace of Pilsen Cinco de Mayo Bar Crawl and Community Celebration
Support your local community by attending Pilsen’s vibrant celebratory bar crawl this weekend! Pilsen is one of Chicago’s many culturally rich neighborhoods, and this year, the community is hosting an 8-stop bar crawl!
Transport around the neighborhood on trolleys as you explore the participating bars including Caminos de Michoacán, la Mejikana, Twisted Cantina, Penny Whistle Tavern, Honky Tonk BBQ, Simones, La Vaca Margarita Bar, and a special mystery bar!
Along with the bar crawl, there will also be a series of ongoing day parties held at local businesses in the area all culminating in the Caminos Block Party later that night!
From cocktail tastings to the annual community celebration featuring live DJs, this exciting celebration is set to take place on Saturday, May 6 from 12 to 8 p.m. with tickets going for $50.
Address: Caminos de Michoacan (1659 West Cullerton Street Chicago, IL 60608)
3. Celebrate Mexico Week at Navy Pier
The Mexican Consulate in Chicago is hosting the 2nd annual Mexico Week this weekend. This year, the consulate is partnering with Jalisco Tourism and the Mexican Consulate with a series of Mexican and Jalisco-inspired cuisine, traditional dance performances, and family-friendly workshops at Navy Pier.
There’s an 18-stop Mexican Food Route, which includes restaurants across Chicago, offering Mexican and Jalisco-inspired dishes and beverages.
Attend the opening ceremony on Friday, May 5th at Navy Pier and the following events throughout Saturday and Sunday. See the full schedule here.
4. Sample and sip at the Latino Spirits Festival
The first annual Latino Spirits Festival is coming to Chicago this weekend (May 6) celebrating Latino spirits from wine to cocktails and more. Guests can attend seminars, sample spirits, and learn about drink origins at this 21+ event. Tickets are going for $65-$95.
Address: Logan Square Auditorium, 2539 N. Kedzie Blvd.
5. See “Destinos al Aire” at the National Museum of Mexican Art this month
The Chicago Latino Theater Alliance is hosting the 4th annual Destinos al Aire, a free outdoor family-friendly festival celebrating the Latin-centric performing arts and entertainment community, and culture.
Head over to the Ray Castro plaza to see Chicago-based Latina comedian Emcee Gwen La Roka emcee the event. She is the first Latina from Chicago to make a comedy special debut on HBO Max.
Featured performances include the Teatro Tariakuri’s Los Chilpayates Youth Ensemble performing a preview of El Baile de los Números, along with an authentic folkloric Peruvian dance performance by The Center of Peruvian Arts featuring Hugo Gutierrez’s performance of traditional Andean music.
Also on the docket, enjoy contemporary Mariachi music, listen to stories at a Story Booth, participate in arts and crafts, and explore many more activities at this yearly event.
Address: National Museum of Mexican Art, 1852 W. 19th St.
From small taquerias to upscale restaurants and more, Chicago is filled with delicious taco-centric options that satisfy no matter what you’re looking for. Check out our top 20 list and go grab a bite to eat (a Carne Asada Taco is always a good idea!) after a weekend of celebration.