CHICAGO — Spend the weekend celebrating Puerto Rican culture in Humboldt Park at the Puerto Rican Fest and Parade, exploring some of the city’s best eats at Taste of Randolph or enjoying street fest season with Andersonville’s hallmark Midsommarfest.
| Site | Subscription Price | Supported Countries |
|---|---|---|
| FuboTV | 5-day free trial, $10–$90/month | USA, Canada, Spain |
| ESPN+ | $11.99/month | USA |
| Fanatiz | €6.99–€10.99/month | Worldwide |
| StreamLocator | 7-day free trial, no credit card required! $9.90/month | Worldwide |
There’s also the Old Town and Wells Street art fairs just blocks apart, a 36th annual horse show celebrating Black cowboy heritage in South Shore, the Artists of the Wall Festival in Rogers Park, Festival Del Niño hosted by the National Museum of Mexican Art, early Juneteenth fests in Bronzeville and Beverly and more. Pride Month events continue as well.
Here’s a roundup of 28 things to do in Chicago this weekend:
All Weekend
Members of La Escuelita Bombera De Corazón performing at an unveiling event for the 44th annual Puerto Rican People’s Parade and festival on June 1, 2023. Credit: Mina Bloom/Block Club Chicago
| Site | Subscription Price | Supported Countries |
|---|---|---|
| FuboTV | 5-day free trial, $10–$90/month | USA, Canada, Spain |
| ESPN+ | $11.99/month | USA |
| Fanatiz | €6.99–€10.99/month | Worldwide |
| StreamLocator | 7-day free trial, no credit card required! $9.90/month | Worldwide |
Puerto Rican Fest
Thursday-Sunday
2800 W. Division St.
The 47th annual Puerto Rican Fest returns to Humboldt Park Father’s Day weekend with live music, dancing, 25 rides (including a Ferris wheel) and over 150 food vendors. The fest also coincides with the Puerto Rican People’s Day Parade June 14.
Tickets start at $17.50. Learn more here.
| Site | Subscription Price | Supported Countries |
|---|---|---|
| FuboTV | 5-day free trial, $10–$90/month | USA, Canada, Spain |
| ESPN+ | $11.99/month | USA |
| Fanatiz | €6.99–€10.99/month | Worldwide |
| StreamLocator | 7-day free trial, no credit card required! $9.90/month | Worldwide |
Mrs. Yuka Layme leads Drag Queen Story Time at Midsommarfest’s Pride Kids event on June 11, 2022. Credit: Kathleen Hinkel/Block Club Chicago
Andersonville Midsommarfest
5-10 p.m. Friday, noon-10 p.m. Saturday, noon-9 p.m. Sunday
Clark Street from Foster Avenue to Gregory Street
Andersonville’s hallmark summer fest features more than 50 musical and entertainment acts across five stages. Performers include The O’My’s, Dancing Queen: An ABBA Salute, J Bambii, Madame Reaper, Merriam Levkowitz, Sixteen Candles and Windy City Cheer. There will be food and drink available for purchase.
There is a $10 suggested donation upon entry. Learn more here.
Taste of Randolph in West Loop on June 16, 2023. Credit: Colin Boyle/Block Club Chicago
Taste Of Randolph
5-10 p.m. Friday, noon-10 p.m. Saturday-Sunday
Randolph Street from Peoria to Racine
For 28 years, Taste of Randolph has brought some of the city’s best cuisine and live entertainment to West Loop. Some food vendors this year include Pitaki, Prince Street Pizza, Porkchop, Gaijin, Matcha Cita and Cafe Tola.
Admission is free, but there is a $10 suggested donation upon entry. Learn more and find the full schedule here.
Art along the Loyola Park lakefront wall from a past Artists of the Wall fest. Credit: Courtesy Rogers Park Business Alliance
Artists Of The Wall Festival
9 a.m.-3 p.m. Saturday-Sunday
Loyola Park’s lakefront wall from Farwell to Morse Avenue
Each year, neighbors and artists come together to decorate a 600-foot wall along the Loyola Park lakefront. There are 160 “artist spaces” of various sizes and shapes, and there will be live music, food, a children’s art tent among other activities while artists color the wall once more. Their art will remain on display until May 2026, when the wall will be whitewashed and prepped for the next fest, which has become a neighborhood tradition.
Learn more about the fest and find the full schedule here.
The Old Town Art Fair in 2019. Credit: Provided/Old Town Art Fair
Old Town Art Fair
10 a.m.-7 p.m. Saturday, 10 a.m.-6 p.m. Sunday
Old Town Triangle Center, 1763 N. North Park Ave.
The Old Town Art Fair is back — and celebrating 75 years since it launched in 1950 — with over 200 artists, a garden walk, live music, a food court and a children’s corner. The event draws tens of thousands of attendees each year.
There is a $12 suggested donation per adult upon entry. Learn more here.
Wells Street Art Fair
10 a.m.-10 p.m. Saturday, 10 a.m.-9 p.m. Sunday
This art fair is back for its 49th year with over 175 artists, food from local restaurants, music performances and art activities for kids.
There is a $10 suggested donation upon entry. Learn more here.
Friday
Kickoff To Summer Picnic
11 a.m.-2 p.m. Friday
Griffin Museum of Science and Industry, 5700 S. DuSable Lake Shore Drive
Enjoy a free community picnic at the Griffin Museum of Science and Industry on Friday. There will be music on a family stage, games, food, hands-on activities and demonstrations.
Learn more here.
Summer Of Peace Kickoff Rally & March
7 p.m. Friday
1210 W. 78th Place
The Faith Community of Saint Sabina is protesting gun violence in Chicago with its Summer of Peace rally and march featuring rapper Vic Mensa and thought leader 19 Keys. There will be free T-shirts for the first 1,000 people.
Learn more here.
Saturday
The Englewood Village Market kicks off this weekend and takes place on select Saturdays through October. Credit: Grow Greater Englewood/Facebook
Englewood Village Market
9 a.m. Saturday
5822 S. Halsted St.
Grow Greater Englewood’s 6th annual Englewood Village Market connects South Side residents with Black-owned businesses, community resources, wellness activities rooted in Black tradition and arts performances. There will be a variety of low-cost fresh produce and prepared food from local businesses.
Learn more here.
Lakeview East 4th Annual Adopt & Shop
11 a.m.-2 p.m. Saturday
Broadway from Belmont to Hawthorne
There will be eight animals shelters along Broadway with dogs up for adoption, local merchants, complimentary goodies for pups and people, pet photo booths and free nail trims at this 4th annual event.
Learn more here.
Festival Del Niño
11 a.m.-3 p.m. Saturday
Harrison Park, 1852 W. 19th St.
Hosted by the National Museum of Mexican Art, this event honors Día del Niño, a spring holiday in Mexico, and children’s well-being. There will be art activities, music and dance performances, games and wellness resources.
This fest is free to attend. Learn more here.
Bronzeville 2025 Juneteenth Celebration
11 a.m.-5 p.m. Saturday
3500 S. King Drive
Celebrate Juneteenth with live performances, art showcases, family fun and shopping from local vendors and small businesses. The theme for this year’s Bronzeville event is “Honoring the Legacy of Freedom: Remembering the Past, Inspiring the Future.”
General admission tickets are free. Tickets for a body scrub-making session are $8.45 and children’s play zone tickets are $8.45. Learn more and buy tickets here.
9th Annual Black Bar Crawl: Beach Edition
11 a.m.-10 p.m. Saturday
Bellagio 223, 2229 S. Michigan Ave.
This 9th annual Juneteenth bar crawl is a celebration of culture and community with music, food and drink specials. There will be a complimentary brunch at Bellagio’s for the first 200 people and an open bar beach party afterward at a secret, to-be-announced location.
Guests are encouraged to wear Afrocentric or Black pride attire with colors like black, green and red. Tickets start at $23.18. Learn more here.
Paw-Fest
Noon-6 p.m. Saturday
Chicago Animal Care and Control, 2741 S. Western Ave.
Chicago Animal Care and Control is waiving all adoption fees for every pet at this springtime adoption event. Every adopted animal will go home spayed/neutered, vaccinated and microchipped.
Learn more here.
Juneteenth Family Fest
Noon-7 p.m. Saturday
110th Place and Longwood Drive
This free Beverly and Morgan Park fest will bring together thousands of attendees for DJs and live music, African dance, family activities, face painting, shopping, food and more.
Learn more here.
Southeast Side Pride Rally
1-5 p.m. Saturday
G.O.D Community Center, 8832 S. Commercial Ave.
There will be food, dancing, live music, vendors, raffles and resources at this 5th annual South Chicago rally.
Learn more here.
A vendor set up a stand to sell Puerto Rican-inspired clothing, jewelry and flags ahead of the Puerto Rican Pride festival and parade, as seen on May 28, 2024. Credit: Ariel Parrella-Aureli/Block Club Chicago
Puerto Rican People’s Day Parade
2 p.m. Saturday
Division Street from Western to Sacramento avenues
The parade is part of Humboldt Park’s Puerto Rican Fest, complete with Bomba y Plena performances, Parrandas and more that will flow into Humboldt Park.
Learn more here.
‘Halation’ Art Show Opening Reception
6-10 p.m. Saturday
Happy Gallery Chicago, 902 N. California Ave.
Chicago-born, Philadelphia-based artist Lily Cozzens is celebrating her solo show “Halation” with an opening reception Saturday evening. Her work is mainly done with oil paint and ballpoint pen and often features horses and dogs “due to their perennial joint history with humankind” and “contradictory nature,” according to her website. For example, horses are strong but easily injured and stubborn but emotive.
The show is up through July. Learn more here.
The Shedd Aquarium is celebrating Pride Month festivities with its annual Pride Night this weekend. Credit: Facebook
Shedd Pride Night
6-10:30 p.m. Saturday
Shedd Aquarium, 1200 S. DuSable Lake Shore Drive
Celebrate Pride Month with a 21-and-older night at the aquarium with DJs and an ocean-themed drag showcase.
Tickets are $14.95-$39.95. Learn more here.
Goddesses, Rage! Artemis Singers Pride Concert & Dance
7-9:30 p.m. Saturday
VanderCook College of Music Great Hall, 3125 S. Federal St.
Artemis Singers, a Chicago lesbian feminist chorus and nonprofit group, is back for a special Pride concert and dance celebrating women’s power and “standing up to The Man.”
Tickets are $27.27 for general admission, or on a sliding scale for $12-$50. Tickets for children 12 and younger are free, and no one will be turned away due to lack of funds. Learn more and buy tickets here.
Sunday
9 a.m.-7 p.m. Sunday
La Cueva Del Indio Cafe, 3500 W. Armitage Ave.
La Cueva Del Indio Cafe and Top Shelf Smoke Shop are hosting its annual Father’s Day block party with food, music by Orquesta Carabali, open mic poetry, a bounce house and vendor tables by Puerto Rican and Latin-owned businesses.
Learn more here.
The American Writers Museum. Credit: Provided/Charlie Simokaitis
Free Day At The American Writers Museum
10 a.m.-5 p.m. Sunday
American Writers Museum, 180 N. Michigan Ave. (2nd floor)
On the third Sunday of each month, the American Writers Museum offers free admission to explore 400 years of history through writing, from exhibits on Chicago writers to Dungeons & Dragons and game writing. There will also be a family-friendly story time at 11:30 a.m.
Online registration is recommended but not required. Learn more here.
The Ramova Theatre. Credit: Joe Ward/Block Club Chicago
Bridgeport Makers Market
11 a.m.-4 p.m. Sunday
Ramona Theatre, 3520 S. Halsted St.
Celebrate Father’s Day with a local market featuring more than 70 artists and makers, food and drinks and a free Father’s Day card-making table. This dog- and kid-friendly event will take over the Ramova Theatre and its beer garden for the day.
Learn more here.
Attendees pose for a picture as they grill chicken during a past Real Men Cook event. Credit: Parnethia Luke/Provided
Real Men Cook
3-6 p.m. Sunday
The Quarry Event Center, 2423 E. 75th St.
This 36th annual event features bites from local cooks, drinks, live music, vendors and family-friendly fun. It’s a celebration of fathers, culture and community.
Tickets are $40 for general admission and $20 for children and seniors. Learn more and buy tickets here.
Event winners Korey Flowers (in blue) and Shaye Scott (in red) pose with Broken Arrow Riding Club founder Murdock, The Man with No First Name, at the 2019 Speed and Action Rodeo Horse Show. Credit: Provided
Speed & Action Rodeo Horse Show
3-8 p.m. Sunday
South Shore Cultural Center, 7059 S. South Shore Drive
Presented by the Broken Arrow Horseback Riding Club, 36th annual Speed & Action Rodeo Horse Show is back this Father’s Day. It will celebrate Black cowboy heritage and urban horsemanship with fast-paced rodeo events, family-friendly fun, vendors, food and more.
Tickets are $15 for general admission and $12 for children and seniors. Learn more and buy tickets here.
Rock Against Tyranny Show
5 p.m. Sunday
Liar’s Club, 1665 W. Fullerton Ave.
Chicago bands TRIPLE, Medicine Ball, the Paper Cups and Mike From Letterbomb will be playing at a Rock Against Tyranny show this weekend. Spend Father’s Day rocking out to “protest songs against authoritarian dictators, war, environmental degradation, extinction of animals and protecting the rights of the LGBTQ+ community.”
Learn more here. A portion of proceeds will go to the American Civil Liberties Union.
The inside of one of Chicago’s lesbian bars, Dorothy, 2500 W. Chicago Ave. Credit: Provided//Riané Human
The Bi Wives Club: A Stand-Up Comedy Showcase
7 p.m. Sunday
Dorothy, 2500 W. Chicago Ave.
This often-sold-out, bi-monthly comedy show is hosting a Pride Month edition this weekend “for all outsiders who hide in plain sight.” The showcase touts itself as being intimate, playful and reliably hilarious.
Tickets are $19.76 online or $20 at the door. Learn more and buy tickets here.
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