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Chicagoist's Guide To August: 21 Fun Things To Do This Month

By Michelle Meywes Kopeny in Arts & Entertainment on Jul 31, 2017 7:05PM

Lollapalooza crowd, photo by Jim Kopeny / Tankboy

Chicago's summer is at its height in August. Make the most of it with our 20 favorite events happening this month.


August 3-6

The music behemoth is back for another year in Grant Park. Once again the sold out festival will span four days and eight stages. With Chance the Rapper, The Killers, Muse and Arcade Fire topping the headliners, this year’s lineup is a draw for the young and not as young as new talent rubs shoulders with alumni acts. If you just can’t bear the thought of braving muddy grounds and inebriated crowds, don’t forget about those official Lolla aftershows at venues all over town. Many of the acts playing the festival also play smaller clubs too numerous to list here.


August 4-6

Jeff Fest shows off the northwest neighborhood of Jefferson Park at their 17th annual community event. The event in Jefferson Memorial Park features something for the whole family with wine tastings and kids' activities plus live music from the likes of The Buckinghams, Too White Crew and 16 Candles. Admission is a $5 donation benefitting the Jefferson Park Chamber of Commerce.


August 5-6

Edge = Edgewater at the annual EdgeFest. The north side neighborhood is on display during the street fest with beer tents, eats and live music. Don’t miss Saturday’s Pet Parade at 11 a.m. Entry is a $5 suggested donation at the gate.

Chicago Picasso image courtesy of the City of Chicago.


August 8

Chicago's Picasso at Daley Plaza has become a recognizable icon of the city since it’s placement in 1967. To celebrate the 50th Anniversary, the city is recreating the unveiling of the sculpture in an event dubbed “Everyone’s Picasso” at noon. The restaging ceremony will also include performances from Chicago Children’s Choir, the After School Matters Orchestra.

The Fly Honey Show, Photo by Megan Lee Miller


August 10-September 2

This annual sex-positive, body-positive burlesque-inspired experimental cabaret is back for another year, this time at the Den Theatre in Wicker Park. The Fly Honeys bring sexy-as-all-heck dancing and performance art to the stage, celebrating "everybody, no matter what your body," and we expect this year to be no different. Opening night is Thursday, Aug. 10, and the show runs on weekend nights from then until Sept. 2 with a rotating ensemble of dancers, artists and musicians. Get in on the fierce, feminist show by purchasing tickets here. Shows at 10:30 p.m., ticket prices range from $23-80.

Chicago Hot Dog Fest 2017 from Chicago History Museum on Vimeo.


August 11-13

A whole festival dedicated to hot dogs? Yes, please. Chicago Hot Dog Fest takes place this weekend outside the Chicago History Museum and they’ll have encased meats from Downtown Dogs, Byron’s Hot Dogs, Chicago’s Dog House, Dog House Grill and many more. They’ll also have live music all day long with Sixteen Candles, Mike & Joe and a Prince Tribute by Robert Cornelius & Friends headlining. Admission is $5.

Image via Retro on Roscoe's Facebook page.


August 11-13

The family-friendly street fest Retro on Roscoe features live bands and an Antique Car Show that fills the weekend. Come prepared to sing along with the familiar tunes of headliners Too White Crew, 16 Candles, Wedding Banned, Mr. Blotto, American English, Trippin’ Billies and The Boy Band Night. Entry is a $10 donation.


August 11-13

This year’s Festival Cubano in Riis Park is chock full of cultural music, food, art and even the costume portion of the Miss Teen U.S. Latina Beauty Pageant. A celebration of freestyle and house music kicks off the weekend on Friday night with Cuban-American DJs Julian Jumpin' Perez and Nayobe, and notable musicians like sonero Michael Stuart and timba group David Calzado y la Charanga Habanera are among the fests other headliners. Admission starts at $15.


August 12-13

Northalsted Market Days is the other big event of the year in Boystown. The Midwest’s ”largest outdoor street fest” always has lively entertainment across several stages and this year offers us Big Freedia, Tiffany, 10,000 Maniacs, the Chicago Gay Men’s Chorus and more. Don’t miss the daily drag shows on the Hydrate Dance Stage. Admission is a $10 suggested donation.


August 12

As if Chance the Rapper wasn’t busy enough, he’ll be the Grand Marshall at this Saturday’s Bud Billiken Parade. This year’s parade is “Honoring our Hometown Heroes” with local youth in bands, drill teams and floats. Parade steps off at 10 a.m. at King Drive and Oakwood with a party to follow at Washington Park.


August 14

Broadway in Chicago’s annual summer concert at Millennium Park offers a free peek at some of the amazing productions underway in Chicago’s theater district. Among this year’s preview performances are Disney’s Aladdin, Escape to Margaritaville, Les Miserables, Waitress, Wicked and more. The curtain rises at 6:15 p.m.


August 18-20

Get a mouthful of Italian culture at Festa Italiana in Little Italy. The neighborhood’s classic restaurants will serve up meatballs, cannoli and more while Italian-American song and dance entertains. Four stages put classic Italian singers alongside rock bands and DJs.


August 18-20

Based on the open air Mexican market known as Tianguis, the 2nd annual Tacos y Tamales Festival hits Pilsen this weekend. Of course there will be boatloads of tacos y tamales from Chicago and Latin America, but also art installations, merchant vendors, Modelo cerveza and live entertainment. Entry is a $5 suggested donation benefiting the Frida Kahlo Community Organization.


August 18-20

Father Apostolos Georgiafentis & Father Chris Mihalopoulos welcome one and all to St. Demetrios’ annual summer festival celebrating Hellenic culture. Lincoln Square Greek Fest celebrates the parish’s 89 years in the neighborhood with authentic Greek food, music, dancing and family-friendly festivities over three days. A $5 donation is requested for entry.

Blue Angels image via Chicago Air & Water Show's Facebook page.


August 19-20

That zooming and roaring you hear in the air in the third week of August is preparation for the 59th Annual Chicago Air and Water Show. Centralized around North Avenue Beach, civilians can marvel at the aerial demonstration teams doing tricks and showing off military operations. This year’s stars are the U.S. Navy’s elite airmen, the Blue Angels and the U.S. Army Parachute Team Golden Knights. Check around town for viewing parties on rooftops and places like The Signature Room atop the Hancock Building.

Image via Sangria Festival's event website.


August 20

Sangria may just be wine, juice and fruit, but it also represents the beginning of a carefree fiesta. Sip on some sangria while enjoying paired cuisine at the weekend’s Sangria Festival in Humboldt Park. They’ll have live music and flamenco dance performances that will make you feel like you’ve landed in a tropical destination. Tickets start at $20.


August 25-27

Sample cuisine of the Mediterranean at the 28th annual Taste of Greektown this weekend. Bites from neighborhood eateries will star along with Greek bands, kids' activities and a gyros eating contest.

Fifth Star Awards image courtesy of DCASE.


August 28

This year will mark the 4th Annual Fifth Star Awards show honoring Chicago arts institutions worthy of another star on the city’s flag. This year’s honorees include hip hop musician Common, architect Jeanne Gang, Civil Rights era painter Kerry James Marshall and Steppenwolf Theatre Company. The free public event in Millennium Park will feature music, acting, poetry and a live concert with Rhymefest, Dee Alexander, JC Brooks, Sam Trump, Nora O’Connor, Toronzo Cannon and Kelly Hogan.


August 30-September 10

The Chicago Fringe Festival showcases 50 performance groups specializing in “the un-tried and the weird” in 200 performances at venues across Jefferson Park. The 11 day festival also includes a fest for the kids, with performances from local acts Barrel of Monkeys, Tiffany Lawson Dance and others. Visit their website for performance schedules and ticket information.

Jazz Fest image courtesy of DCASE.


August 31-September 3

The Chicago Jazz Festival is a Labor Day tradition in the city, this being the event’s 39th year downtown. Millennium Park and the Chicago Cultural Center will play host to performances from local musician Jon Faddis, pianist Jason Moran, The Rebirth Brass Band from New Orleans and more, plus tributes to legends Dizzy Gillespie, Thelonius Monk and Ella Fitzgerald. Admission to all Jazz Fest events is free. Visit the event website for the full schedule.


August 31-September 3

Check out the pros for free when the AVP Beach Volleyball Gold Series tour hits Oak Street Beach this weekend. General Admission viewing is free and seating is first come first serve. For an elevated view with shade and food, Club AVP VIP tickets are for sale.