Where to Celebrate Cinco de Mayo 2026

Raised, An Urban Rooftop Bar

This year, Raised is leaning into two featured holiday cocktails:

• “Choose Your Own Adventure” Margarita: For those who want a personalized touch, this starts with a classic margarita base and allows guests to customize their drink with a variety of fruit and herbal flavor additions.
• Oaxacan Old Fashioned: A smoky, elevated riff on a classic, featuring Tequila, Mole bitters, Demerara syrup, and a signature spritz of mezcal.

Pinstripes (Oakbrook & Northbrook)

Cinco de Mayo technically falls on a Tuesday this year, but Pinstripes is getting the party started early with a specialty weekend brunch. Offered Saturday, May 2 and Sunday, May 3 from 9 a.m. to 2 p.m., guests can enjoy Pinstripes signature brunch buffet with a few festive additions:

• Chilaquiles Omelet Station (featuring house salsa verde, tortilla chips, pesto chicken, sour cream, cheddar and mozzarella, and guests’ choice of condiments)
• Mini Churros (tossed in toasted cinnamon sugar and topped with powdered sugar with chocolate and caramel sauce)
• Mexican Pizza (featuring guaca verde salsa, mozzarella, shaved prime rib, jalapenos, red onion, cilantro and sour cream)

In addition to the brunch features, Pinstripes will also have a lineup of new May Margaritas in collaboration with Matthew McConaughey’s Pantalones Tequila, including:

• The Garden Glow: Featuring Pantalones Blanco Tequila and flavors of fresh mint and cucumber.
• The Spring Fling: Featuring Pantalones Blanco Tequila, with lychee and coconut.
• The Desert Bloom: Featuring Pantalones Blanco Tequila, the Desert Bloom brings Texas to the Windy City with Pinstripes’ take on the classic prickly pear margarita.

The Cinco de Mayo Brunch will feature a DJ both days from 11 a.m. – 2 p.m. Pricing starts at $35 for adults, $16 for kids 6-12 and kids 5 and under are free.

Robert's Pizza Dough & Co. 

The pizzeria will be celebrating on Saturday, May 2nd, with all-day specials and a live Mariachi band! Grab a seat on the expansive riverside patio (it's dog-friendly!) or head inside while grabbing your favorite pies or something new to try. A Mariachi band will be performing from 1pm - 3pm on Saturday, 5/2, and specials (available May 1-5) include:

• $33 Margarita Flight: spicy mango, cucumber, and strawberry
• Chicken Tinga Pizza: chicken in adobo sauce with onions, fresh mozzarella, and Monterey Jack topped with radish, chopped onion, queso fresco, salsa verde, sour cream, and cilantro
• Cochinita Pibil Pizza: achiote oil, habanero salsa, fresh mozzarella, pulled pork, shredded cheese, queso fresco, pickled red onion, and cilantro
• Shrimp Ceviche: mango, cucumber, red bell pepper, tomato, red onion, jicama, jalapeno, serrano, lime juice, and tortilla chips
• Flan: egg custard with caramel, whipped cream, and almond cookie
• Guac or Pico de Gallo & Tortilla Chips

City Works Eatery and Pour House 

City Works is launching limited time offerings on April 22, just in time for Cinco de Mayo including a Lavendar Margarita, Spicy Watermelon Paloma, Pastor Pork Tenderloin and Funfetti Funnel Cake. Guests can enjoy these items until June 16.