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Friday, May 3, 4-9pm
For a taste of a variety of Latin-inspired street food, Latinicity is the food hall to visit. Located on the third level of Block Thirty Seven at 108 N. State St., Chef Richard Sandoval’s stylish market with eight kitchens hosts a pre-Cinco de Mayo celebration on Friday, May 3. The event starts at 4pm with happy hour drink specials. DJs Kevin Allen and Marquez Antonio will also spin house beats and records from 5:30pm to 9pm If you can’t make it to Friday night’s party, Latinicity will offer $3 tequila shots and $4 beers plus more specials through the weekend.
Friday, May 3, 8-10pm
The Slide Bar is a friendly neighborhood spot that offers late night snacks, burgers and chicken sandwiches as well as an extensive list of domestic and imported beers. If you’re looking for a pre-party, the tavern will host music from Vivian Garcia, sangria, and a 25% discount on select Spanish-style tapas.
Friday-Sunday, May 3-5
Margaritas, fajitas and tacos are just three items this Tex-Mex restaurant does well. For Cinco de Mayo, Tuco and Blondie (3358 N. Southport Ave.) has an entire weekend of events planned, such as kids’ crafts at 11am Friday, and face painting at 11am Sunday, as well as music and patio games for adults. On the food and drink side, the restaurant offers huitlacoche tamale specials from 6pm to 8pm Friday-Sunday, $7 Muralitas from 8pm to 10pm Friday-Sunday, and build-your-own-’rita and grilled taco bars at designated times on Saturday and Sunday. Check out the full schedule and RSVP here.
Saturday, May 4, 7-9pm
A casual Mexican restaurant located at 3400 N. Ashland Ave., Cafe El Tapatio is known for its mix of traditional-yet-authentic and inventive-yet-delicious fare. On Saturday, May 4, the restaurant hosts a Cinco de Mayo party from 7pm to 9pm, featuring mariachi music, complimentary cocktail tastings and $7 Corazon margaritas and $5 Don Julio Reposado shots.
Saturday, May 4 - Sunday, May 5
Chef Martial Noguier’s French modern gastropub isn’t the first (or even twentieth) restaurant that probably comes to mind when thinking, “Where can I go for a Cinco de Mayo special?” However, the restaurant at 840 N. Wabash Ave. will offer brunch and dinner specials on Saturday and Sunday to mark the occasion. Brunch features a two-course $25 prix fixe menu, and bottomless Mexican mimosas for $20. Dinner options include a three-course $39 prix fixe menu, as well as other menu items available a la carte.
Sunday, May 5, 12pm-3pm
A newer restaurant that’s known for its range of classic and specialty tacos served on handmade tortillas, Tatas Tacos (at 4929 W. Irving Park Road) is celebrating its one-year anniversary during the Cinco de Mayo weekend. Two parties in one? Yep. On Sunday, May 5, the restaurant will roll a grill outside on the patio for al pastor tacos, offering one free taco per customer from 12pm to 3pm, while quantities last. The anniversary party also includes spin-the-wheel prizes, raffles and music.
Sunday, May 5
An Argentine steakhouse serving aged steaks to go along with its music and tango classes, Artango Bar & Steakhouse (4767 N. Lincoln Ave.) will serve specials on Sunday, May 5, including $7 margaritas all day, taco and Mexican breakfast specials during brunch service, 10am to 3pm; as well as dinner specials from 4pm to 10pm.
Sunday, May 5, 10am-3pm
A sports bar that opened last March from the owners of Hubbard Inn, Old Grounds Social (950 W. Wrightwood Ave.) has enough TVs to catch every angle of every game while chowing down on a burger, flatbread or order of smoked chicken wings. For Cinco de Mayo Sunday, the pub will offer special brunch items as well as a Michelada bar from 10am to 3pm and margarita towers. Reservations required. Get more information here.
Sunday, May 5
Half-liquor store and half-neighborhood tavern, Maria’s Packaged Goods and Community Bar (960 W. 31st St.) hosts a day-long party the first Sunday of each month. Lucky for them, and us, the party is happening on Cinco de Mayo. The shop’s Brunch-Ski runs Sunday, May 5, with a Brunchlox brunch menu by Cindy Knott running from noon to 4pm, and Kimski dinner menu of Korean-Polish-inspired street food starting at 5pm Six DJs will also spin records from noon to 8pm And what about drinks? More than 40 beers on tap, hundreds more in bottles and cans, and craft cocktails will be served. RSVP and get more info here.
River North and Gold Coast
Sunday, May 5, 12-3pm
A casual restaurant with two locations less than two miles away from each other, Blue Agave has tons of tequilas, Tex Mex fare and a selection of guacamoles. For Cinco de Mayo Sunday, both locations (River North at 579 W. Kinzie, and Gold Coast at 1050 N. State St.) offer bottomless tacos and margaritas from noon to 3pm. Two drink tickets will also be given for customers to make their margaritas at the margarita mixology bar. All that for $45. Ages 21 and up. Tickets will not be sold at the door. River North info; Gold Coast info.
Sunday, May 5, 10am-11pm
A Chicago fixture and designated city landmark that reopened in 2017, this 15,000 square-foot steakhouse (1401 S. Michigan Ave.) is running food and drink specials on Sunday, May 5, from 10am to 11pm. Those deals include $10 Espolon margaritas, $4 tacos, and $3 chips and dips.
West Loop Fulton Market
Sunday, May 5 after 5pm
An exotic, eclectic and massive restaurant, Carnivale (702 W. Fulton St.) blends flavors from Central and South American countries. On Sunday, starting at 5pm, the restaurant offers a Cinco de Mayo menu, featuring an appetizer taco platter with chicken al pastor, lomo encebollado (pork loin), pork adobo; entrees of cochinita pibil (Yucatan-style braised pork and sides of refried black beans and plantains) and carne asada (habanero-marinated hanger steak); chocolate crepe for dessert; and a selection of cocktails. Reservations are recommended.
Sunday, May 5, 11am-2pm
This bar and restaurant at 1419 N. Wells St. is teaming with Chicago Sport and Social Club for a Sunday Cinco de Mayo brunch from 11am to 2pm. For $35, patrons get a Mexican-themed brunch buffet and three hours worth of bottomless drinks like Coronas and Bloody Marys. After brunch, customers can stick around for drink specials, or enjoy one of the 90 craft beers on tap. Get tickets and more information.
Sunday, May 5, 1-4pm
Formerly Lobo Rey, this casual Tex-Mex restaurant at 1307 S. Wabash Ave. reopened in March with a new focus and name -- The Lobo Canteen. While the menu has changed a little bit to make room for shared plates like Mexican pizzas and Tex Mex wings, the bar/restaurant still offers tacos and foot-long quesadillas (good lord). On Sunday, the restaurant hosts a “Sunday Funday Cinco de Mayo” day party from 1pm to 4pm with live music, an open bar and an unlimited taco station. Tickets start at $55. Get more information and RSVP here.
Sunday, May 5, 6-10pm
Mexican street food gets a sophisticated twist at this restaurant’s north side location at 4217 Ravenswood Ave. On Sunday, the restaurant hosts a Cinco de Mayo wine and cheese tasting event featuring paintings from artist Tania Gonzales that pay tribute to the legendary Frida Kahlo. Live dancers will also perform throughout the event. Tickets are $30-$35.
Sunday, May 5
Contemporary, casual and a consistent stop for trivia and game nights, D.S. Tequila Co. serves a la carte tacos, burgers and quesadillas as well as margaritas served in a regular mug or a fiesta bowl (that’s 40 ounces of margarita). On Cinco de Mayo Sunday, the bar and restaurant hosts an all-day brunch patio party from 11am to 11pm, including drink specials like the $19.95 mimosa package from 11am to 3pm. Reservations recommended. RSVP and get more information.
Sunday, May 5 starting at 1:30pm
The specialty grocery store that makes Whole Foods seem like Aldi (I’m only guessing, because when looking up Vom Fass, I yelled aloud to my wife, “what in the hell is a Vom Fass?”) will host a Cinco de Mayo tequila tasting at its location at 4755 N. Lincoln Ave. Starting at 1:30pm Sunday, ticketed patrons can taste a range of tequilas as well as a few small apps. Tickets are $35.
Sunday, May 5, 12-2pm
Karaoke meets a beer garden with a seafood-style menu at this bar at 3216 N. Sheffield Ave. On Cinco de Mayo, Trader Todd’s has created a new tradition with its annual Cinco De Meow event. Running from noon to 2pm Sunday, the restaurant will serve up Mexican-style dishes and drinks and host raffle prizes and trivia for the no-kill animal shelter Felines & Canines. $30 gets you food and two drink tickets. Get more information and tickets here.
Sunday, May 5, 12-4pm
This sports bar serves up chicken wings and burgers, has a wall of TVs, and Yelp reviews that start with “I am not going to lie.” Yep, Flagship Tavern and Grill sounds like a pretty good place to go for a beer and bar food while watching “Riverdale,” I mean, the game. On Sunday, Flagship (1622 W. Belmont Ave.) hosts all you can eat tacos (chicken, steak, fish and rajas) and all you can drink beers (Corona, Pacifico, Modelo, Sol) from noon to 4 p.m. Tickets are $40.
Sunday, May 5, starting at 8pm
Just two blocks from Michigan Avenue, located inside the intimidatingly hip Freehand Hotel, Broken Shaker offers craft cocktails, small bites and a couple of plates of bar food. While all of it is pretty swanky and gussied up in that “mixology” “handcrafted” world, it’s also all pretty delicious. So on Cinco de Mayo at 8pm, this little hotel bar hosts a pop-up featuring Puerto Rican-inspired cocktails and cuisine from La Factoria. Get more information and RSVP.
Friday, May 3 - Sunday, May 5
Las Fuentes is a local chain with patio seating, combination plates, tamales, tacos and other standard favorites of neighborhood Mexican restaurants. The restaurant’s three locations will celebrate Cinco de Mayo all weekend long with a special menu, margarita bar, music and pinatas.
River North, Printers Row, University Village, Hyde Park locations
Friday, May 3 - Sunday, May 5
A gastropub-style chain with a huge menu of burgers, apps, beers and cocktails, Bar Louie’s four Chicago locations will feature “Cabo de Mayo” specials all weekend long. The main attraction is highlighting rocker Sammy Hagar’s Santo Mezquila. The restaurant and bar will also feature specials on select drinks and plates, including two tacos for $5.
Sunday, May 5, 12-3pm
Shared plates, tacos and ceviches are just a few food options at Mercadito, a Southern Mexican-style restaurant from chef Marissa Tuñon. For Cinco de Mayo, the restaurant at 108 W. Kinzie St. will host from noon to 3pm Sunday a three-hour open bar with interactive drink and complimentary food station as well as passed items. Tickets are $65 per guest, plus tax and gratuity. Ages 21 and up. Make your reservation and get more information.
Friday, May 3 - Sunday, May 5
El Nuevo Mexicano offers cozy vibes and traditional dishes as well as vegan and vegetarian options. Over the Cinco de Mayo weekend, the restaurant at 2914 N. Clark St. will offer $5 Herradura shots and $8 silver coin margaritas as well as prizes and giveaways on Friday, May 3, free tequila samples from 6pm to 8 pm Saturday, May 4, and a mariachi band on Sunday, May 5. RSVP and get more information.
Friday, May 3 - Sunday, May 5
Upscale tacos, truffle street corn guacamole and shared plates await when you visit Barcocina (2901 N. Sheffield Ave.). Throughout the Cinco de Mayo weekend, the modern Mexican restaurant will offer specials like $10 off margarita pitches on Friday; and a $35 drink package with Mexican beer, house margaritas, chips, salsa and guacamole from 10pm to 12:30am on Saturday. Get more information and RSVP here.
Friday May 3 - Sunday, May 5
Award-winning chef and Chicago restaurant all-star Rick Bayless and his hip brewery will get in on the Cinco de Mayo fun. Bayless’ Cruz Blanca Brewery & Taqueria (904 W. Randolph St.) will serve tacos, cerveza and margaritas all weekend long. Reservations recommended. More information is available here.
Sunday, May 5
An upscale chain known for its happy hour specials and modern Mexican fare, Cantina Laredo will host a ton of Cinco de Mayo festivities and deals on Sunday, including DJ DaVinci from noon to 8pm, margarita specials, $5 Tecate, special cocktails, and a new brunch menu from 10am to 3pm, followed by dinner until 10pm.
Sunday, May 5, 10am-3pm
WestEnd Bar is the the neighborhood hangout for Blackhawks and Bulls fans, loaded with TVs, bar far and drafts and craft beer. On Sunday from 10am to 3pm, the bar/restaurant/lounge at 1326 W. Madison St. hosts a $10 walking taco bar and $10 bring-your-own Bloody Maria’s. To add, WestEnd will serve $4 tequila shots, $5 Micheladas, and $8 margaritas. RSVP and get more information.
The J. Parker
Sunday, May 5, starting at 2pm
Rooftop views on Cinco de Mayo? The J. Parker is offering that and more. The restaurant above Hotel Lincoln at 1816 N. Clark St. hosts a Cinco de Mayo Mezcal party at 2pm Sunday. The event features a Mezcal cocktail list, music and a $2 street taco bar. Registration is free at Eventbrite.
Bar Crawl de Mayo
Saturday, May 4, 11am-6pm
Hop from bar to bar from 11am to 6pm Saturday during Bar Crawl de Mayo. For $20, Participants get a t-shirt, brunch buffer, and three $4 gift cards to use during the crawl. The crawl schedule will be announced Friday, May 3. Bars to be crawled include Moe’s Cantina, Old Crow, Bar Louie, Tunnel, Rockit, Pink Taco and others. The lineup is scheduled to change. Ages 21 and up. Get more details, tickets and RSVP here.
Cinco de Mayo Pilsen Cantina Crawl
Saturday, May 4, 12-6pm
Sip tasty cocktails, enjoy live music and have a good time to support the upcoming Pilsen Fest 2019. From noon to 6pm Saturday, the lower west side neighborhood will host its sixth annual cantina crawl, which features mezcal and tequila cocktails served at more than 10 Pilsen bars and restaurants. Tickets are $30-35. Ages 21 and up. Get more information and tickets here.
Saturday, May 4, doors at 6:30pm
Prepare for a night of Spanish and Mexican hip-hop at the landmark music venue the Vic Theatre, at 3145 N. Sheffield. The all-ages concert features performances from MC Magic, Lil Rob, Amanda Perez and Akwid. Doors open at 6:30pm. Tickets are $50-$65.
Bangers and Lace in Wicker Park
Saturday, May 4, 12-8pm
Local beers, brats, street vendors and a skateboard competition are all planned during this Cinco de Mayo Street Party from noon to 8pm Sunday at Bangers and Lace at 1670 W. Division St. The free, kid-friendly party features a skate ramp supplied by the good folks at Cream City Skateboard Park, Solemn Oath’s specialty brews, a skate trick competition hosted by Pardon My Thrashing, and drink specials. RSVP and get all the details here.
Tequila-N-Tacos TNT Bar Crawl
Saturday, May 4, 12pm
Tequilas and tacos are the draw of major Cinco de Mayo events around the city, so get a lot of both of them during this party that starts at the Trophy Room (170 W. Ontario St.) at noon Saturday. Tickets are $15-$20 and include a free t-shirt, complimentary taco bar at check-in locations and entry to four venues that will be announced closer to the date. Ages 21 and up. RSVP and get more information.
East Room in Logan Square
Saturday, May 4, 8pm
Some of the hottest DJs in the city will spin cumbia, salsa, merengue, hip hop and more during East Room’s Pachanga De Mayo party starting at 8pm Saturday at the bar at 2354 N. Milwaukee Ave. The event includes spinning sessions from DJs Solmeca, Ca$h Era, Iggy, Dewey Depp, Memo Duarte and Roger McFly as well as live music from Navarro, Zianna and Mariachi Sirenas. Stick around for the midnight caballo dorado contest. $10 cover. Get more information.
Near North Side
Saturday, May 4, 10pm-midnight
Considered one of the area’s premiere dance and nightclubs, the Underground (56 W. Illinois St.) hosts a Cuatro de Mayo party Saturday with VIP cocktail reception from 10pm to midnight and live performances from Strategy and Dolo. Tickets are $20 and include admission and express entry before 11:45pm. Ages 21 and up.
Thalia Hall in Pilsen
Sunday, May 5
Chicago’s Academy of Mexican Dance & Music hosts a Cinco de Mayo Fiesta from 3pm to 9pm Sunday at Thalia Hall (1807 S. Allport St.). For $15, patrons of all ages can enjoy live music, dance performances, food and art vendors. Doors open at 2pm. Get tickets here.
Chicago Tacos and Margs Crawl
Sunday, May 5, starting at 12pm
Nearly 10 bars are participating in Bar Crawl Nation’s Chicago Tacos & Margs crawl. The event highlights some of the area’s best spots while giving patrons prizes along the way, themed specials and free cover to the participating venues. Tickets are $22.99. The event starts at noon Sunday at Emporium Chicago (1366 N. Milwaukee Ave.) and hits High Noon Saloon, Whiskey Business, Cheesie’s Pub & Grub, Swig, Debonair Social Club, Standard Bar/Grill, The Tankard and Pint Chicago. Ages 21 and up. More information is available here.
Cinco de Mayo Pub Crawl
Sunday, May 5, 1pm
Neighborhood bars and restaurants around Wrigley Field are even getting in on the Cinco de Mayo action as PubCrawls.com hosts the third annual Wrigleyville pub crawl party. Registration starts at 1pm Sunday at Lucky Strike Social (1027 W. Addison St.), then patrons will get access to drink specials at participating venues to be updated before the event. Tickets are $15. Get all the information and RSVP here.
Cinco de Drinko Booze Cruise
900 S. Wells, Chicago
Sunday, May 5, 1:30-5:30pm
Do all your partying on a flippin’ boat during this event running from 1:30pm to 5:30pm Sunday. This booze cruise will take patrons on the Chicago River and Lake Michigan and has two levels of music and drinking. Boarding begins at noon on the Summer of George. Ticketed passengers must board 10 minutes before the 1pm departure time. While early bird tickets are sold out, general admission tickets for $25 are still available. More information is available here.
Rooftop Party at Apogee Lounge
Sunday, May 5, 2-6pm
Meet People Chicago sets up at Apogee Lounge in the Dana Hotel at 2 W. Erie St. for a party with music, drinks, food and a photo booth from 2pm to 6pm Sunday. Tickets are $5 and up. Register and get more information.
CSO Chamber Music Series: Celebrating Latin American Art
Fullerton Hall at The Art Institute of Chicago in Millennium Park
Sunday, May 5, 2pm
Chicago Symphony Orchestra hosts an afternoon concert of Latin American dance rhythms from four contemporary composers. The show starts at 2pm Sunday and features works from Alberto Ginastera, Astor Piazzolla, John Zorn, and Metro Chabacano. Tickets are $33 per person. Registration is required. More information is available here.
Afrobeats n’ Chill
Room 2 in River North
Sunday, May 5, starting at 3pm
In the mood for a more laid back Cinco de Mayo? Head to Room 2 on Sunday at 3pm at 738 N. Clark St. for this Cinco de Mayo edition of Afrobeats n’ Chill. The $5 cover gets you access to drink specials as well as grooves from Mo Gwala and DJ KO. RSVP, register and get all the info here.
Sunday, May 5, doors at 3pm
While The Promontory does offer an upscale, modern dining experience at its location at 5311 S. Lake Park Ave. W., for Cinco de Mayo, you’ll want to visit the bar/restaurant’s music space. On Saturday, the club at The Promontory will get things going early, opening doors at 3pm while DJs Dark Knight, Kev and Commando spin records to 9pm. Early bird admission is $10, $20 for general admission. Get more information and tickets here.
River North Bar Crawl
Sunday, May 5, starting at 5pm
PROMO SE7EN hosts its third annual Cinco de Mayo bar crawl at 5pm Sunday. Festivities began at Cafe Disko then run over to Bottled Blonde from 7pm to 10pm, Bounce Sporting Club from 10pm to 2am, then Liqrbox from 2am to 4am. Tickets are $20-$35 and include a t-shirt, mustaches (?!) and discounted drinks. Get more information here.
Cinco de CAP-o
Sable Kitchen & Bar in River North
Sunday, May 5, 5pm
Some of the country’s best bartenders meet at Sable Kitchen & Bar (505 N. State St.) for a night of delicious cocktails for a good cause. The Cinco de CAP-o event starts at 5pm Sunday, benefitting the Helen David Relief Fund which aides bartenders affected by breast cancer. Participating bartenders shaking up a Cinco de Mayo-inspired cocktail include Richard Beltzer of Bad Hunter, Angie Caballero of Bellemore, Alexis Belton of The Aviary, and Jenee Craver and Dante Torres of Sable Kitchen & Bar. RSVP and get more information here.
Fiesta de Baile
Center on Halsted in Lakeview
Sunday, May 5, 7pm
The Lakeside Pride Latin Band honors the relationship between the Latinx and LGBTQA communities with a red-hot set of music at 7pm Sunday at Center on Halsted (3656 N. Halsted St.). Tickets are $10. More information is available here.
The Comedy Bar/Brewery Stage at Gino’s East in River North
Sunday, May 5, 8pm
Jaime de Leon hosts a Cinco de Mayo comedy night at 8 p.m. Sunday at The Comedy Bar inside Gino’s East at 500 N. LaSalle Dr. The show features some of the area’s favorite Spanish-speaking comedians. General admission tickets are $10 at Eventbrite. Ages 17 and up. For more information, call (312) 836-0499 or click this link.