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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.


The ultimate event for Chicago foodies, this high-end festival features 10 parties at 10 iconic locations, as well as cooking demos by celebrity chefs including Rick Bayless, Stephanie Izard, and more. The main event in Millennium Park showcases over 250 Chicago restaurants, as well as hundreds of vintners, spirit makers, and breweries from throughout the world.

  • When: Tue Sep 19 – Sun Sep 24
  • Where: see schedule
  • Hours: see schedule
  • Admission: starts at $40
  • More Info:


The best of international LGBTQ cinema, showcasing a range of genres and voices, are presented along with multiple opportunities to speak with the filmmakers themselves. Reeling is the second longest-running festival of its kind, and offers everything from social documentaries to experimental shorts.

  • When: Thur Sep 21 – Thur Sep 28
  • Where: Landmark Century Centre (2828 N Clark) and Music Box Theatre (3733 N Southport)
  • Hours: see schedule
  • Admission: Screenings $10 – $12, passes $45 – $130
  • More Info:


The acclaimed creator of A Prairie Home Companion offers a singular evening of Midwestern storytelling, captivating audiences with a unique blend of comedy, class, charisma, and wisdom. Keillor is one of America’s most treasured radio personalities, and his live show is certain to brighten your mood.

  • When: Sat Sep 23
  • Where: Center Theatre (9501 Skokie Blvd, Skokie)
  • Hours: 8pm
  • Admission: starts at $63.50
  • More Info:


Featuring 11 stages across Hyde Park, this festival is stacked with notable local talent, including Andrew Cyrille and Bill McHenry, Amina Claudine Myers, the Jeremy Pelt Quintet, and much more. This year will also mark the 100th birthday of jazz legend Thelonious Monk with four special programs.

  • When: Sat Sep 23 – Sun Sep 24
  • Where: see schedule
  • Hours: Sat 1pm – 12am, Sun 1pm – 7pm
  • Admission: Free
  • More Info:


This internationally acclaimed contemporary dance company led by MacArthur Genius Grant recipient Shen Wei comes to Chicago for the first time to debut two of his signature works: Folding and Rite of Spring. Shen draws on a myriad of influences, and is most famous for his awe-inspiring choreography featured in the 2008 Olympics Opening Ceremony in Beijing.

  • When: Sat Sep 23 – Sun Sep 24
  • Where: Auditorium Theatre of Roosevelt University (50 E Congress Pkwy)
  • Hours: Sat 7:30pm, Sun 2pm
  • Admission: starts at $29
  • More Info:

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