With summer (finally, belatedly) upon us, Chicagoans might be more inclined to hit the beach or their neighborhood street festivals than to waste daylight sitting in a dark theater. But enjoying the summer heat and taking in a play don’t have to be mutually exclusive — the warmer months bring a slew of theater productions to Chicago’s parks, from Shakespeare to kids’ shows to documentary plays. With 2019 designated the Year of Chicago Theatre, there’s more programming this summer than ever. And every performance listed here is free to attend. Grab your camp chairs, spread a blanket, pack a picnic, and see a story unfold under the sun or stars.

Millennium Park Summer Theatre Residencies

Millennium Park will be the backdrop for nine local troupes from July to October. Highlights include Chicago Dance Crash’s Belly of the Whale, a hip-hop rendition of Pinocchio’s encounter with marine life staged in Crown Fountain (July 26–27), and La gran tirana: Descarga teatral (The Great Tyrant: A Theatrical Descarga), a Spanish-language piece from Aguijón Theater inspired by Cuban soul singer La Lupe (August 13–17). View the full schedule at millenniumpark.com.

Theater on the Lake

Theater on the Lake isn’t as outdoors as it used to be, or at least since the renovation to make it suitable for year-round use was completed in 2017. But the Lincoln Park facility still has stunning lakeshore views, and it continues its summer tradition of hosting short-run remounts of the past year’s buzziest Chicago storefront productions — a mini-festival for FOMO-averse theatergoers. This year’s best bets include the Neo-Futurists’ Tangles & Plaques (August 13–16) and Steep Theatre Company’s staging of Ike Holter’s Red Rex (August 27–30). This summer’s shows are all free to attend, but since seating is limited, reservations are recommended; get all the info at theateronthelake.com.

Chicago Shakespeare in the Parks

Chicago Shakespeare Theater packs up for an annual tour of Chicago Park District venues, bringing a kid-friendly cutting of one of the Bard’s best to a green space near you. This summer’s offering is The Comedy of Errors, a goofy farce involving two sets of twins and lots of opportunities for mistaken identity, presented in a 75-minute abridgement. The troupe’s stage on wheels will visit more than a dozen parks around the city until August 18; see the complete itinerary at chicagoshakes.com/parks.

Midsommer Flight

Every summer since 2012, this ensemble has mounted no-frills outdoor stagings of one of Shakespeare’s best-known works, proving you need little more than actors and words to hold an audience’s attention. This year the company tackles The Tempest, the fantastical tale of vengeance and romance set on an enchanted island; Stephanie Monday plays the traditionally male role of the wizard Prospero. The touring production bounces back and forth among four different parks through August 25; find the full schedule at midsommerflight.com.

Free Street Theater

Marking its 50th anniversary this summer, Free Street looks back and ahead in Still/Here: Manifestos for Joy and Survival. The new performance is born out of story workshops held across the city, in which facilitators asked local residents to imagine Chicago’s ideal future. Catch one-off performances at the South Shore Cultural Center (July 25), Humboldt Park (July 27), Cornell Square Park in Back of the Yards (August 1) and Walsh Park in Bucktown (August 3), culminating in a weeklong run at Cloud Gate Plaza in Millennium Park (October 6–12). Visit freestreet.org for details.


This two-decade-old company has evolved its mission in recent years to become explicitly focused on social-justice issues affecting Chicago. So Collaboraction’s erstwhile annual event Sketchbook, a festival of new short works mounted in a DJ-driven, clublike atmosphere, is now Peacebook, touring the city’s parks with programs of theater, dance, and spoken-word pieces that share a more activist-leaning, community-organizing mindset. This year’s edition launches with a weekend of performances at Kennedy-King College (August 15–16) before visiting La Follette Park in North Austin (September 13–14), Douglas Park (September 20–21) and Hamilton Park in Englewood (September 28–29). Book of Peace, a collection of highlights from five years of Peacebook, will follow at Millennium Park (October 4–6). Get more information at collaboraction.org.

Walkabout Theater

For something a little more avant-garde, look to this intermittently active troupe whose creations are often site-specific. Some of Walkabout’s memorable past projects include a mesmerizing movement piece staged in a laundromat (2005’s Psycho-So-Matic), a clownish take on “Captain” George Streeter performed in community gardens (2008’s War Garden), and a moving anthology of short works set throughout a Lincoln Square church (2013’s All Rise). So while details are still sketchy on The Raveling, described as a surrealist family-history drama, we’re already intrigued. Catch it at Near North Side’s Seward Park (September 10–11), Independence Park in the Irving Park neighborhood (September 13–14), Burnside’s Tuley Park (September 19), or Sherman Park in Back of the Yards (September 21). Check out walkabouttheater.org for updates.