Chicago Bust out the sombreros and ponchos -- we’re rounding up five asombroso Cinco de Mayo parties that’ll have you yelling “Whoa, these Cinco parties are totally asombroso, good thing I busted out my sombrero and poncho!”

Megan Osterhout

Pioneer Tavern Group: The good people behind Frontier, Lottie’s Pub, and The Pony are offering a complimentary “Dos de Mayo” bar crawl. Trolleys will be running from 7pm-1am on the half-hour between all three venues, which'll be stocked with Dos Equis promo girls, plenty of beer, $5 Palomas, and $6 tacos. Also: participate in Best Mustache and Best Sombrero competitions. Also ALSO: grow a mustache/bring a sombrero.
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High Noon

High Noon Saloon: Frontera vet Chef Ruben Beltran is adding limited-edition $3 Cinco sliders made with roasted chicken thigh, mole poblano, pasilla, ancho, and guajillo chiles to High Noon's Tex-Mex menu. Enjoy 'em with $4 Pacifico drafts, $3 tequila shots, $8 margs, and the celebratory sounds of Mariachi Mexico Vivo.


AyChiwowaChi

¡AY CHIWOWA!: Kill two birds with one stone at ¡AY CHIWOWA! this weekend. On Derby Day, guzzle $14 Derby 'Ritas, $5 Maker’s Mark cocktails, and bet on ponies while supporting Habitat for Humanity. Keep the festivities rolling with a Cinco de Mayo party on Monday that’ll feature $5 tortas and taquitos, $15 Corona buckets (for sharing dude, for sharing...), and $7 margs.

Tavern on Rush

Tavern on Rush: Head to the Viagra Triangle for an all-day fiesta packed with $1 (!!!) steak tacos, $2 tortilla chips and salsa olé, $2 homemade pork tamales, and $3 bottles of Corona. Ole!

Bull & Bear

Bull & Bear: Hit this tavern’s all-day, all-night Cinco de Mayo party, featuring peppers stuffed with Jack, aged cheddar, Chihuahua cheese & chorizo, mini barbacoa tacos, and mini churros accompanied by RumChata-infused chocolate sauce. There’s no cover, and they’re offering three margarita varieties all served in complimentary cactus glasses (!) that you can take home afterward (!!).


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1. Frontier 1072 N Milwaukee Ave, Chicago, IL 60642

It may not be the final frontier, but with ice-taps pouring 16 traditional and seasonal brews, a meat heavy menu featuring specialty sausages, steaks, and "Animal Service", flat screen TVs, and a beer garden, you won't need to explore any further. Allied: Ready yourself for Animal Service with some Smith & Forge, the hard cider that's built strong -- built from Apples and built to Refresh.

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2. Lottie's Pub 1925 W Cortland St, Chicago, IL 60622 (Bucktown)

Born in 1934 as a destination for Chicago’s mobsters to gamble and indulge in prostitution, the modern-day Lottie’s promises its guests beer, bar snacks, and a little slice of history. The pub has, obviously, undergone renovations, but its exposed brick walls, wood paneling, and various memorabilia help maintain its old-time, neighborhood atmosphere. Now offering a full menu of bar food favorites -- chicken tenders, nachos, burgers, pizza, and the like -- and a large selection of cheap beer, the two-story dive draws a mixed demographic to its corner in Bucktown.

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3. The Pony 1638 W Belmont Ave, Chicago, IL 60657 (Lakeview)

Co-founded by the guy behind Lottie's, The Pony's an upscale tavern replete with hickory-slatted walls and floors, wood-beamed ceilings, a 38ft copper-plated bar, and bucket-style stools to keep your tush securely stable during high-performance drinking.

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4. High Noon Saloon 1560 N Milwaukee Ave, Chicago, IL 60622

Are you a fan of Tombstone? The 1993 film, not the popular frozen pizza brand. Because you can get an Old West feel and stop eating from the freezer section thanks to High Noon Saloon, a Tex-Mex tequila bar sporting a spur-scuffed hickory floor, olde-tyme photography, butcher block tables, and fringed leather stools.

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5. Ay Chiwowa 311 W Chicago Ave, Chicago, IL 60654 (Near North Side)

Ay Chiwowa's a late-night cantina with cool graffiti decor, 80 different tequilas, and a menu with snacks like tacos and tortas.

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6. Tavern on Rush 1031 N Rush St, Chicago, IL 60611 (Gold Coast)

Tavern on Rush's got a charcoal-grilled Wagyu ribeye chop... need we say more??

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7. Bull & Bear 431 N Wells St, Chicago, IL 60654

Located in the heart of North River, B&B is a perfect spot for any meal of the day. They feature the likes of fantastic burgers and especially tasty brunch options, all in a space decked out with classic, rustic materials.

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