5 Of The Best Annual Chicago Neighborhood Festivals

Wednesday, February 6th, 2019

Depending on who’s counting, a list of Chicago’s neighborhoods can number into the 200s. Come summer months, it seems as though each of them hosts a festival of some sort, defined by the local culture, commerce, cuisine — or just a desire to get outside with neighbors and invite the whole city over for a beer.

The beauty of Chicago is finding your favorites. Here are five festivals that are always among the best.

  1. Actually, this is two – Old Town Art Fair and Wells Street Art Festival both take place on the same weekend (June 8 and 9 in 2019), both feature more than 200 artists and coexist a few blocks apart in the beautiful Old Town neighborhood.
      Art Fair is 71 years old and boasts the added feature of a garden walk through more than 50 area backyards. Art Festival came along about 25 years later and is the wilder of the two, offering longer hours to take advantage of the bars and restaurants that dot its Wells Street setting. Old Town’s suggested donation at the gate is $10 and Wells Street’s is $8.
  2. Looking for things to do near Old Town Chicago?

  3. Gorgeous gorging — Taste of Chicago fills Chicago’s front porch — Grant Park’s beautiful greenspace, bordered by Lake Michigan and the high-rise majesty of the Loop and South Loop — with food, music and literally millions of visitors to enjoy it all.

    Looking for things to do near Old Town Chicago?

      The 2018 Taste featured 72 food vendors, including 22 pop-up vendors and 13 food trucks, and an estimated 1.5 million visitors over five days. The 2019 Taste runs July 10-14. Admission is free, but you’ll have to purchase food and drink tickets.
  4. Get Lit — Readers unite! The Printers Row area of the South Loop was once a publishing hub. Since 1985, what was originally the Printers Row Book Fair and is now the Printers Row Lit Fest has celebrated that history. Around 200 authors will be on hand to discuss and sign their works. Dozens of booksellers are browsed by patrons that will number into six digits over two days, June 8 and 9 in 2019. Admission is free, but some events require tickets.
  5. Let it Rainbow — In 1997, a six-block stretch of Halsted Street in the Lakeview neighborhood was recognized by then-Chicago mayor Richard Daley as the first official gay neighborhood in America. By that point, Northalsted Street Market Days already had been celebrating the Boystown lifestyle for 17 years.

    Looking for things to do near Old Town Chicago?

      In 2019, the August 10-11 fest, billing itself as the largest street festival in the Midwest, expects to welcome more than 200,000 visitors to a half-mile stretch of North Halsted, where four stages, 200-plus vendors, food, drink and people-watching will keep the party going. There is a $10 suggested donation for admittance.
  6. Get the Blues — Chicago is where the blues went electric. That heritage gets its due each summer in spectacular Millennium Park with the Chicago Blues Festival, the 36th edition of which will be held June 7-9, 2019.

    Looking for things to do near Old Town Chicago?

    The biggest acts are featured at the Jay Pritzker Pavilion, just across Randolph Street from Lakeshore East’s stunning modern high-rises. Three other stages around the park allow for more intimate performances. Admission is free.

Fests for the Rest

If the preceding festivals don’t pique your interest, don’t give up. Maybe Bike the Drive is more your thing, or Riot Fest or Lincoln Park Greek Fest would be more to your liking. With so many festivals in easy reach, developing your own “best of” is half the fun.

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