There are so many fun things to do this weekend in Chicago including these cultural events, concerts, festivals and more.  Enjoy – you deserve it!


1. The Rolling Stones

  • When:   June 21 & 25, 2019 at 7:30 pm.
  • Where:  Soldier Field, 1410 S Museum Campus Dr, Chicago IL 60605.

Why this is fun:  Just a few weeks after postponing its North American tour so that Mick Jagger could undergo heart surgery, the Rolling Stones have announced that it’s back on again. Any other aging front man might have taken a bit more time to recuperate, but Jagger is already posting Instagram videos of himself dancing and strutting like a regular “Jumpin’ Jack Flash.”

As has been the case for the past decade, the Stones don’t have any new music to promote (though the group recently released yet another greatest hits compilation), so you can expect a setlist that’s heavy on the group’s sizable trove of singles. Plus, the Stones are known for trotting out a few surprise guests—during the band’s three-night stand at the United Center in 2013, Taylor Swift, Sheryl Crow, Taj Mahal and Mick Taylor joined the band onstage. It’s anyone’s guess as to who the band might rope in for its latest triumphant jaunt through the states.

For more details, visit the website. 


2. Chicago Jerk Festival

  • When:  June 23, 2019, doors open at 10:00 am until 10:00 pm.
  • Where:  Washington Park, 5533 Russell Dr, Chicago IL 60601.

Why this is fun:  The 2nd Annual Chicago Jerk Festival is gearing up to welcome thousands of patrons to Washington Park Sunday June 23rd from 10am until 10pm. The South Side will experience the sights, sounds and spicy aromas of the Chicago Jerk Festival, a daylong extravaganza featuring exotic Caribbean and American food— many grilled to perfection— live music, authentic Caribbean influenced arts and crafts souvenirs and activities for kids of all ages. The Jerk Festival concept which highlights Caribbean food and entertainment has become a national concept.

For more details, visit the website.


3. Chicago Pride Fest

  • When:  June 22 and 23, 2019 starting at 11:00 am.
  • Where:  Boystown from 3600 to 3800 N Halsted, Chicago IL 60613.

Why this is fun: The 19th annual Chicago Pride Fest®, June 22-23, 2019, is a legendary two-day street festival held the weekend leading up to the Chicago Pride Parade with up to 100,000 expected to attend, celebrating LGBTQ+ life, culture and community. This year marks a milestone as we honor the 50th anniversary of Stonewall and the birth of the Pride movement.

The festival features live music by popular artists, 4 stages, food and drink, 100+ arts/craft and merchant vendors, DJ’s and dancing, drag shows, pet parade, Out At Wrigley National Anthem Singing Contest, sponsor booths and more.

For more details, visit the website.


4. World’s Largest Block Party

  • When:  June 21 & 22, 2019 – Friday 5:00 pm to 10:30 pm & Saturday at 2:00pm to 10:30 pm.
  • Where:  Old St. Patrick’s Church, 700 W Adams St, Chicago IL 60661.

Why this is fun:  While it may not set any world records with its attendance, this annual bash at Old St. Patrick’s Church is a beast of a block party, benefiting the institution’s social justice and outreach programs. World’s Largest Block Party fills a parking lot near the church with food, beer, a bags tournament and music from local cover bands 16 Candles and 7th Heaven. Lock down your ticket before June 10 to score a free drink upon arrival or show up between 5 to 6pm on June 21 for free entry to the event.

For more details, visit the website.


5. Dragon Boat Race for Literacy

  • When:  June 22, 2019 from 8:00 am until 5:00 pm.
  • Where:  Ping Tom Memorial Park, 1700 S Wentworth Ave, Chicago IL 60616.

Why this is fun:  The Chinese Dragon Boat Race dates back to over 2,000 years and is a popular sport amongst Chinese and Asian communities all over the world. Started in 2000, the Chicago Dragon Boat Race for Literacy is a family-fun activity enjoyed by visitors from all over the city and surrounding suburbs.

Thirty-two dragon boat race teams will compete on the south branch of the Chicago River in beautifully decorated dragon boats, each consisting of up to 20 members: 18 paddlers, 1 drummer and 1 flag catcher. The 18 paddlers row to the beat of the drummer, while the flag catcher of each team pulls a flag positioned in the water at the finish line. Races begin at 8 am. The Opening Ceremony begins at 9 am.

In addition to the exciting races, guests can enjoy riding a free Chinatown Trolley which will travel from the park and loop around Chinatown during the event from 9 am – 4 pm. There will also be children’s activities, vendor booths and entertainment programming throughout the day including beautiful Chinese dancers, exciting performances by the Hōkūleʻa Academy of Polynesian Arts, music and more!

For more details, visit the website.


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