What to Do in Chicago Each Day of August 2019

This is where we'll be all month.

August 1: Lollapalooza—Armed with dozens of bands stretched across the massive Grant Park, Chicago’s answer to Coachella returns for another year with the biggest names in music. In addition to headlining acts from Ariana Grande, Childish Gambino and Tame Impala, we’re also excited to check out an eclectic mix of artists performing during this four-day fest. Smino and Saba both represent Chicago’s thriving rap scene, while country pop songstress Kacey Musgraves and pop soul queen Janelle Monae are always a delight to see live. Also August 2-4

August 2: Chicago Cubs Vs. Milwaukee Brewers—Get the family together for a thrilling afternoon at Wrigley Field and watch the first place Chicago Cubs take on one of their fiercest rivals, the second place Milwaukee Brewers. The first 10,000 fans get a free pair of collectable Cubs pajama pants.

August 3: Black Harvest Film Festival—The Siskel Center in downtown Chicago hosts the Black Harvest Film Festival, an annual exploration of powerful Black filmmakers from around the world. In addition to a wide variety of movies made here in Chicago, the highlights include a 25th anniversary screening of Spike Lee’s “Crooklyn,” and a showing of “Premature” which debuted to acclaim earlier this year at Sundance. Also August 4-29.

August 4: “Cats”—The winner of seven Tony Awards and arguably Andrew Lloyd Webber’s greatest masterpiece, “Cats” ends its latest Chicago run at the James M. Nederlander Theatre. Today is your last chance to witness the magic and whimsy of the theatrical production before the movie adaptation starring Taylor Swift and Jennifer Hudson comes out later this year. 

August 5: National Oyster Day Patio Soirée—Need a breather after Lolla? Frontier has you covered. Today is National Oyster Day and to celebrate, the award winning Noble Square bistro is running a special of $5 glasses of rosé and $1 oysters. 

August 6: Barbra Streisand—In support of her 36th album, “Walls,” the iconic Barbara Streisand makes an increasingly rare appearance in Chicago with a performance at the United Center for an enrapturing evening of pop classics such as “Woman in Love.”

August 7: Running of the Bulldogs—You don’t need to go to Spain to run with the bulls. All you need to do is head to downtown Chicago and check out Mercat a la Planxa, a bistro inspired by the culture of Barcelona. The clever Running of the Bulldogs event offers a special eight-course tasting menu of tapas and paella that directly benefits the Chicago French Bulldog Rescue, and they’ll also host some very adorable pups. Runs through September 12.

August 8: Bowie Ball—Celebrate the life and art of the legendary David Bowie tonight at trendy Logan Square nightclub East Room with DJs spinning the best of Ziggy Stardust all night long.

August 9: Chicago Hot Dog Fest—The Chicago-style hot dog is an essential pillar of the city’s culture—so much so that the Chicago History Museum has organized the Chicago Hot Dog Fest this weekend in Lincoln Park. Sample authentic Vienna Beef hot dogs prepared by Luella’s Southern Kitchen and more creative preparations from some of the best chefs in town. Also  August 10-11.

August 10: 64th Annual Ginza Holiday Festival—Based in the quaint north side neighborhood of Old Town, the Ginza Holiday Festival is the Midwest Buddhist Temple’s celebration of Japanese culture. Get the family together and spend the afternoon watching master craftsmen demonstrate building techniques that date back to feudal Japan, as well as listening to traditional Japanese folk music and eating delicacies such as chicken teriyaki. Also August 9 and 11.

August 11: Northalsted Market Days—Here’s a fun fact: The Chicago district of Boystown was America’s first recognized gay village. This weekend, the neighborhood celebrates their heritage by throwing a massive party with over 200 unique vendors and performances from Icona Pop, Deborah Cox and Sheila E. Also August 10.

August 12: “Aquaman”—Tonight, Navy Pier is hosting a free screening of “Aquaman” on the lakefront so you can get caught up on Jason Momoa’s aquatic adventures before his headlining appearance at the Wizard World comic book convention later this month.

August 13: “True West”—In the early ‘80s, the Steppenwolf Theatre became a player in the American theatre scene with their groundbreaking production of “True West.” Written by Sam Shepard, the play is a character study of two brothers with a turbulent relationship who find themselves trapped in their childhood home. Armed with a new generation of artists, “True West” makes its triumphant return with a two-month run at the Steppenwolf. Runs through August 25.

August 14: Grant Park Music Festival—For 85 years, the Grant Park Music Festival has been a summer institution in Chicago with world-class orchestras showcasing the grace and power of classical music. Tonight, head to Millennium Park for a performance of “Flight of the Bumblebee” from the famed Russian opera, “The Tale of Tsar Saltan.” Runs through August 17.

August 15: Smashing Pumpkins—In support of their new album, “Shiny and Oh So Bright…,” the iconic Chicago-based alternative rockers play a homecoming show tonight at the nearby Hollywood Casino Amphitheatre with Noel Gallagher’s High Flying Birds.

August 16: Ali Wong—Fresh from her breakthrough performance in Netflix’s “Always Be My Maybe,” Ali Wong is bringing her raunchy yet sophisticated stand-up comedy to town at the illustrious Chicago Theatre. Also August 17.

August 17: Chicago Air and Water Show—Head over to North Avenue Beach in the heart of the city to get front row seats to the Chicago Air and Water Show. The largest event of this kind in the country features daring pilots soaring through the sky in military fighter jets, plus helicopters and more. Admission is free. Also August 18

August 18: Apple Picking at Kuipers Family Farm—Fall is almost here again! Take a quick road trip to the nearby suburb of St. Charles for your first chance of the year to pick apples under the brisk summer sun, all while enjoying a delicious batch of apple cider doughnuts. Runs through October 31.

August 19: U.S. Pizza Museum 1st Anniversary—It isn’t a secret that Chicago takes pizza VERY seriously. We have a whole museum dedicated to the savory pie, and it’s full of historical artifacts from the golden age of Pizza Hut as well as fascinating curios. Today, the South Loop-based U.S. Pizza Museum celebrates its one year anniversary with, what else, a pizza party as part of the Chicago Tribune’s Food Bowl series of culinary events.

August 20: Goat Visits // Bee Demo—Escape the calamity of city life and explore peaceful gardens at the Garfield Park Conservatory. Spend the day with goats at the picturesque west side garden. In addition to being the perfect backdrop for your next selfie, the goats help maintain the plant population by grazing the fields. Today, the Garfield Park Conservatory also hosts a beekeeping demo to explain the importance of these tiny winged creatures. Both events are free to the public.

August 21: Wine of 99—Join City Winery on the 99th floor of the iconic Willis Tower for a wine tasting in the sky. Marvel at the stunning beautiful architecture of downtown Chicago while sampling wines from the award-winning West Loop winery.

August 22: Wizard World—One of the premiere comic book and pop culture conventions in the country returns this weekend. Head to McCormick Place and spend the afternoon taking selfies with some of Chicago’s best cosplayers, marvel at what's next for Marvel Comics and meet celebrities as Melissa Joan Hart and Aqauaman himself, Jason Momoa. Also August 23-25.

August 23: Chicago Jazz Festival—Anchored by a breathtaking performance by pianist Eddie Palmieri, the Chicago Jazz Festival returns to Millennium Park for another year of showcasing what is new and noteworthy in the world of jazz. Runs through September 1.

August 24: Neon Summer—With a massive go-kart track located on a two-acre field in the heart of Goose Island, Neon Summer invites you to escape the ordinary and go on an urban adventure featuring mini-golf, food trucks, axe throwing, cocktails and more! Runs through September 8.

August 25: Chicago Triathlon—Head downtown and cheer on friends, family and athletes from around the world as they swim, bike and run through the city in an amazing race to the finish line. Also August 24.

August 26: Nose to Tail Wine Dinner—Located in the heart of the chic Lakeview neighborhood, Ella Elli is a dapper bistro that celebrates cuisine from around the world. Tonight, they’re hosting an outdoor patio pig roast. Experience a four-course tasting menu that features a whole roasted pig with dishes such as charcuterie with housemade pickles and porchetta with herb-caper vinaigrette, all of which have been expertly paired with wines by a sommelier.

August 27: Shedd Aquarium—Make friends with a dolphin, watch a shark glide through the water and maybe even meet a penguin as the famed Shedd Aquarium, which opens their doors to Illinois residents for free this week. Also August 26.

August 28: Alejandro Sanz—The winner of 17 Latin Grammys and a pillar of the Latin rock community, Alejandro Sanz is an acclaimed flamenco-influenced guitarist from the sunny shores of Madrid. Tonight, he makes a rare appearance in the Chicago area for a performance at the Rosemont Theatre as he tours America in support of his new album, “El Disco.”

August 29: “Toni Morrison: The Pieces I Am”—Acclaimed by film critics across the country and a hit at Sundance, “Toni Morrison: The Pieces I Am” is a documentary about the life, creative process, activism and legacy of the “Beloved” author. It ends its Chicago run tonight at the Gene Siskel Film Center. 

August 30: North Coast Music Festival—Chicago’s destination electronic dance music festival turns 10 this weekend at Northerly Island with blockbuster performances from Bassnectar, Major Lazer and more. Also August 31.

August 31: The Great American Lobster Fest Chicago—Head on downtown to Navy Pier and spend the afternoon sampling succulent lobsters flown in from the freshwaters of the East Coast at the Midwest’s largest seafood festival. In addition to stuffing yourself silly with lobster, enjoy live music, cold drinks, and family friendly activities for the little ones. Also August 30 & September 1.