One of the many perks of living in the Windy City is knowing that world-class food is never far away. While you can find global cuisine on every corner, Cinco de Mayo in Chicago is truly special because of our plethora of authentic Mexican restaurants.
Whether you’re looking for a sunny patio, hand-shaken margaritas, or the best al pastor in the Midwest, we’ve curated the ultimate guide to help you eat, drink, and be merry. Here are our top picks for celebrating Cinco de Mayo in Chicago this year.
This holiday trumps any Taco Tuesday you've ever celebrated. For the most authentic experience, skip the chains and head to these local favorites.
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There’s always big news at this Wicker Park staple. On Cinco de Mayo, Big Star often pairs up with its neighbor, Dove’s Luncheonette, to offer unique breakfast tacos and early-bird specials.
Pro Tip: Expect a line, but the patio atmosphere and the bourbon-heavy margaritas make the wait entirely worth it.
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You could have the perfect Cinco de Mayo meal at Rick Bayless’ inviting neighborhood Mexican Bistro and Bar. Start with choose-your-topping guacamole, grab a torta, pair it with a hand-shaken margarita and then pull it all together with a stack of churros. At XOCO their freshly-fried, melt in your mouth churros are paired with a chocolate shot. XOCO’s chocolate is unlike any other in the city, because according to their website they are "the only restaurant in Chicago with its own bean-to-cup chocolate program. Huge sacks of cacao beans arrive at our door from Tabasco."
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Replacing the old Taco Joint spot as our River North/West Loop go-to is Texan Taco Bar. Boasting a massive rooftop with views of the Chicago skyline, this is the place to be for high-energy vibes. Look for their "Tecate and Taco" bundles and their signature "Quesdizzas."
Pro Tip: Interested in exploring more West Loop eats? Join us on Gateway to The West Loop Food Tour
With the closure of Nana, The Duck Inn has become the neighborhood's premier patio destination. While known for their duck fat dogs, their Cinco de Mayo specials often feature elevated takes on Mexican classics like kingfish ceviche and slow-roasted pork.
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Try the House Rosemary Margarita. The simple mix of tequila and fresh lime is elevated with rosemary simple syrup. It’s available by the pint and the quart for those planning to go big!
For a funky twist, try their Horchata Margarita. This Logan Square dive bar has one of the best secret patios in the city.
If you’re looking for more than just a meal, Chicago hosts several annual events that bring the fiesta to the streets.
Every May 5th, Carnivale hosts one of the biggest parties in the city. Expect Mariachi bands, live dancers, cigar rollers, and specialty tequila flights. Their $8 classic margaritas and taco stations make it easy to celebrate all night long.
For a healthier way to celebrate, the Cinco de Miler is a 5-mile and 5k race that usually takes place the Saturday closest to the holiday. This year's race has moved to a vibrant new course through the West Loop, finishing with a huge party featuring breakfast burritos, horchata, and live Mariachis.
If tacos aren't your thing, head to the West Loop’s Greek Town. While the rest of the city is fighting for a spot at a taqueria, you can enjoy $5 appetizer specials and a lively atmosphere that still feels like a celebration, just with more pita and saganaki!
To learn more about Chicago's best foodie spots from Mexican favorites to iconic local spots, book a tour with Chicago Food & City Tours today!
