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5 Things to Do Around Chicago This Weekend

Celebrate that you finally made it through the week with five awesome events around Chicago this week! Every week we at Dream Town scour the city and handpick five things we’re excited about.

From culture and history, to weird culture and history, to checking out some art and theatre; you’ll have no shortage of things to talk about next Monday.

Block Party

World’s Largest Block Party

Now in its 35th year, Old St. Pat’s annual fundraiser draws crowds from all over the city for a jam-packed weekend of music, food, and fun. Funds from this unique event help strengthen the organization’s mission of social justice—get out and party for a good cause!

  • When: Fri Jun 21 – Sat Jun 22
  • Where: Old St. Pat’s Campus (Monroe St and Desplaines St)
  • Hours: 5pm – 10:30pm Fri, 2pm – 10:30pm Sat
  • Admission: $10
  • More info:

90s Run

I Love the 90’s 5K Run

Ready to get jiggy with it? Take a run back in time to the days of plaid flannel shirts and flip phones this Saturday. Be sure to check out the post-race 90s celebration, immediately after the fun run. Grab those fanny packs and run!

  • When: Sat Jun 22
  • Where: Montrose Harbor (601 W Montrose Dr)
  • Hours: 8am
  • Admission: $49
  • More Info:


Vegandale Festival

Back for its fourth year in Chicago, this all-vegan fest highlights some of the best plant-based bites and drinks. 100% vegan—from food to merchandise—this unique fest is a great way to experience something new.

  • When: Sat Jun 22
  • Where: Grant Park Butler Field (100 S Lake Shore Dr)
  • Hours: 11am – 7pm
  • Admission: $15
  • More Info:

Pride Fest

Chicago Pride Fest

Celebrate diversity, equality, and the Chicago LGBTQ+ community at Pride Fest! Featuring live music, dancing, 100+ arts/craft merchants, a pet parade, and so much more, this year’s love-filled festival marks the birth of the Pride movement.

  • When: Sat Jun 22 – Sun Jun 23
  • Where: Halsted St, from Addison to Grace St
  • Hours: 11am – 10pm
  • Admission: $10 suggested donation
  • More Info:

Evanston Garden

Evanston Garden Walk

Go behind the scenes of some of the suburbs’ most amazing gardens! Showcasing 9 private and public gardens—including a century old hidden garden listed on the National Registry of Historic Places—proceeds from the 30th annual Evanston Garden Walk help provide scholarships for children to attend the Evanston Ecology Center’s summer camps.

  • When: Sun Jun 23
  • Where: Various locations
  • Hours: 12pm – 5pm
  • Admission: $20 – $30
  • More Info:

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