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Roller Skating, A House Music Festival And More: 15 Things To Do In Chicago This Weekend

An early Oktöberfest, live jazz music, street festivals and more — there's something for everyone this weekend in Chicago.

People dance at the SummerDance in the Parks series at Portage Park in Chicago's Portage Park neighborhood; September 2021.

CHICAGO — Summer isn’t over yet, and neither are the city’s street markets and festivals.

Here’s a roundup of 15 events across the city with music, food, art, family-friendly activities and more.

Music at Mayfair

2-3:15 p.m. Saturday

4400 W. Lawrence Ave.

Local musician, artist and activist Stann Champion will perform.

Way Too Early Oktöberfest

Noon-6 p.m. Saturday

Solemn Oath Brewery, 2919 W. Armitage Ave.

Traditions from the world’s greatest beer celebration are headed to Logan Square this weekend. Enjoy traditional German fare at this free-to-attend pop-up.

Myron Laban’s ‘Time to Rise’ Art Exhibition

6-8 p.m. Friday

The Silver Room, 1506 E. 53rd St.

Check out artwork by Chicago artist and pharmacist Myron Laban at his “Time to Rise” exhibition, which features a series of his colorful acrylic paintings focused on themes of perseverance and healing.

South Asia Institute Freedom Festival

1-6 p.m. Saturday-Sunday

South Asia Institute, 1925 S. Michigan Ave.

The South Asia Institute is hosting its inaugural Freedom Festival. It will have two days of cultural music and dance performances by local and international artists. You can register for this free-to-attend event here.

The event is in conjunction with the institute’s current exhibition, “Unbearable Memories, Unspeakable Histories: Partition Anti-Memorial Project,” which will be open during the festival.

Retro on Roscoe

5-10 p.m. Friday, noon-10 p.m. Saturday-Sunday

Roscoe Street and Damen Avenue

This three-day street festival features live entertainment, an antique car show, family-friendly games and crafts, bites from local restaurants and more.

Life Out Loud Chicago 2022

8-10 p.m. Saturday

Arcade Park, 11149 S. St. Lawrence Ave.

Pullman residents can listen to true-life stories told by friends, neighbors and fellow Chicagoans at the fifth annual Life Out Loud event. Bring a blanket or chair and expect to hear tales of love, loss, close encounters, bizarre coincidences and more.

Popcorn and lemonade will be provided. The event is free and open to the public. 

Mujeres Empoderadas Vendor Fest

11 a.m.-5 p.m. Saturday

Our Lady of Nazareth Parish parking lot, 11128 S. Avenue G.

Shop from more thann 40 small businesses at the first Mujeres Empoderadas Vendor Fest. There will be a DJ and food.

My House Music Festival

3-10 p.m. Saturday-Sunday

Harrison Park, 1824 S. Wood St.

Experience two days of music, local food and merchandise vendors, art and more at this sixth annual fest in the birthplace of House Music. Tickets are available starting at $30 here. People 12 and younger can enter for free with an accompanying adult.

Edison Park Fest

5-10 p.m. Friday, noon-10 p.m. Saturday-Sunday

6730 N. Olmsted Ave.

Enjoy live entertainment, a beer garden, food vendors, a bags tournament and more at this neighborhood fundraiser. Admission is free with a $5 suggested donation to support the Edison Park Chamber of Commerce.

Sunday Backyard Jazz

4-7 p.m. Sunday

8110 S. Luella Ave.

Grab a chair and enjoy music by Felena Bunn this weekend as part of the South Side Jazz Coalition’s Sunday Backyard Jazz summer series. Tickets are $10.

The Rainbow Skate On Catalpa

6:30-10 p.m. Friday

Catalpa Avenue between Clark Street and Ashland Avenue

This pop-up roller skating event has skating on the street, music and games for the family. It is free — just bring your own skates — and open to the public.

Little Italy Festa

5-10 p.m. Thursday-Friday, noon-10 p.m. Saturday-Sunday

Taylor Street in Little Italy

Chicago’s Little Italy Festa celebrates the neighborhood’s Italian culture, cuisine and history. There will be food from local restaurants, stages with family entertainment, merchandise from Italy and more. The festival returns after being canceled two years in a row due to COVID-19.

Bud Billiken Parade

Starts 10 a.m. Saturday

King Drive between 39th and 55th streets

The famed Bud Billiken Parade will celebrate kids returning to school with local dance teams, music, high-energy performances and more.

Lady Gaga Drag Brunch

11 a.m. and 2 p.m. Saturday

The Walnut Room Chicago, 111 N. State St.

Get $20 tickets for a Lady Gaga drag brunch here. The event is hosted by Lucy Stoole and features Lady Ivory, Pixel and Angelïca Grace. Each guest must buy an entree.

Bronzeville Summer Nights

5-8 p.m. Friday

East 43rd Street

Bronzeville Summer Nights is back for its 10th anniversary, celebrating and promoting commerce in the neighborhood. Visit local businesses for live pop-ups, surprise entertainment, family-friendly events and more. View a list of Bronzeville businesses here.

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