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Lively Cinco de Mayo Celebrations in the Chicago Loop

Posted  3 years ago  in  Loop List, Trending

Want to know where to go for Cinco de Mayo? The Chicago Loop has fantastic specials for the celebration of the May 5 holiday honoring the Mexican army’s victory over France at the battle of Puebla in 1862. Sneak in a siesta before you fiesta, and enjoy some of the hottest deals in town.

Cuatro de Caballo at Cerise Rooftop

May 4

Virgin Hotels Chicago marks the arrival of summer and re-opening of Cerise rooftop with a Cuatro de Caballo Party, celebrating both Cinco de Mayo and The Kentucky Derby in one fabulous party. It’s an all-day event filled with Chandon champagne and goodies with ’80s jams by DJ Brock Manke and Greg Corner, and late night tropical sounds by Tengo Funk. Learn More


May 3

Latinicity and Groove Foundation have teamed up to host a pre-Cinco de Mayo celebration on Friday, May 3, at Latinicity on Level 3 of Block 37. Happy hour is from 4-6 p.m. with drink specials, including $3 tequila shots, $4 beers, and more. Kevin Allen and Marquez Antonio will drop house beats from 5:30-9 p.m. Learn More

Cinco de Mayo Deals at Stock and Ledger

April 29 – May 5

During the week of April 29, enjoy Cinco de Mayo and Kentucky Derby-inspired cocktails and snacks at Stock and Ledger. Feed your appetite Triple Crown Wings and Steak Nachos, or better yet, work up an appetite for a Cinco de Mayo-inspired lunch menu. With a $10 cocktail menu featuring Mint Julep and Passion Fruit Margarita, you can start your festivity at this sustainable restaurant tucked away in the premier Theatre District. Learn More

Photo Courtesy of Stock and Ledger

Derby de Mayo weekend at City Winery Riverwalk

May 5

Celebrate Cinco de Mayo with DJ Lovebug, spinning from 2-6 p.m. and sipping on Don Julio Palomas, premium flights, and taking shot specials at City Winery Riverwalk. Chef Donte Carthans will offer special Pork Carnitas Tacos in addition to his delicious Mediterranean fare. Learn More

Cinco de Mayo Treat at Sugar Bliss

May 1 – May 5

Have a sweet tooth? Celebrate Cinco de Mayo with a spicy cinnamon chocolate cupcake from Sugar Bliss Cake Boutique. It also offers morning pastries, made-to-order crepes, tarts, cookies, and brownies. In the summer, Sugar Bliss brings out its famous cupcakes, cake pops, French macarons, and ice pops. Learn More

Want a quick bite before you get festive? Dos Toros is your go-to casual taqueria, offering authentic, San Francisco Mission-style burritos, platos, salads, quesadillas, and tacos using fresh, sustainably-sourced ingredients.

If you’re going to drive to the Loop, download the iParkit mobile app for discounted parking at any of InterPark's 18 city-wide locations. It will give you easy access to the city's best attractions. Millennium Garages also offers multiple convenient parking garages, and you can secure your spot ahead of time online. If you are going to be drinking, we recommend you take a Lyft or the CTA for a safe ride back home. Click here to plot your route.