
Is there anything more alluring than a summer night in Chicago? The lakefront beaches, the meandering pathways, the festivals and street foods, the hidden gardens where free art productions are staged, whatever you like, you can find it in the city during summer evenings. There is no shortage of parks to explore or cultural events to experience, thanks in part to the Mayor’s Night Out in the Parks program that partners with organizations to stage free artistic experiences in neighborhood parks all around the city. One such organization kicked off its summer series with a spectacular – and free – performance of Shakespeare’s As You Like It, now playing throughout Chicago parks through August 2nd.
Shakespeare’s As You Like It is a comedy that follows Rosalind and Orlando, two lovers who each run away from their own political and familial problems and escape into the Forest of Arden. Disguised as a shepherd boy, Rosalind finds Orlando and convinces him to woo her under the guise of curing him of his love for Rosalind. Multiple couplings occur, lessons of life and love are expounded on, and, as every Shakespeare comedy does, As You Like It ends with a wedding – four to be precise.

foreground - Thomas Russell and Connor O. Locklin. Photo by Steven Townsend, Distant Era.
As You Like It is the 2026 production of Midsommer Flight, a theatre troupe that stages high-quality, accessible performances of Shakespeare’s plays in Chicago. Directed by Producing Artistic Director Beth Wolf, this summer’s production continues to delight audiences and draw crowds, presenting free performances to Chicago communities that aim to bring people together. Midsommer Flight is an Arts Partner with Chicago Park District and a participant in the Mayor’s Night Out in the Parks initiative. They will be performing the classic Shakespeare comedy throughout the summer at different neighborhoods throughout the city, but if you think you’ve seen a Shakespeare production, (seen one, seen them all, right?) I beseech you to venture to one of the parks. At the best of times, Shakespearean stories can be difficult to follow: analogous phrasing, double entendres, prosaic old-timey insults, and slurs; it’s not always easy to follow. Midsommer Flight, however, gives the old texts modernity, witty asides, and an expressive atmosphere that makes the play easy to follow and understand. The acting is superior, and the inclusivity is a delightful and refreshing display of humanity at its finest. Talent of the Midsommer Flight cast would rival that of any Shakespearean theatre company, charging hundreds of dollars for seats, and staging productions in grand halls. And the best part? The productions are completely free to the public. The accessibility, the garden park scenery, and the flowy costuming truly provide a magical experience, embodying the spirit, humanity, and beauty of the arts.
There are many benefits to living in and around the Chicagoland area, but summertime really brings out the best and brightest Chicago has to offer. Night Out in the Parks is but one of the many incredible accessible programs bringing cultural events to neighborhoods to “amplify the artistic and cultural vibrancy of our city in every neighborhood and enhance quality of life across Chicago.” Find out more about Night Out in the Parks here. When initiatives such as this meet the grassroots talent and love shown by Midsommer Flight, magic happens. Whether you like it because it’s in your local park or you like it because it is free, there is truly something for everyone this summer in Chicago. You can truly have it just as you like it. As You Like It will be performed outdoors at six Chicago parks through August 2nd. Learn more about Midsommer Flight and its mission, and check out the list of upcoming performances at parks throughout Chicago and reserve your free space today!
MidsommerFlight is a not-for-profit theatre company committed to presenting Shakespeare’s plays to everyone in an IDEA manner: Inclusive, Diverse, Equitable, and Accessible; and to bringing the Shared Joy that results to underserved communities about Chicago.
MidsommerFlight has staged productions of ‘As You Like It’, ‘The Tempest’, ‘Macbeth’, ‘Hamlet’ and others, in various parks around the city. TWELFTH NIGHT has been its Holiday production since 2015 (skipping 2020) and is held in the lush Chicago Conservatory. Admission is pay-what-you-can (suggested donation $30).
Though TWELFTH NIGHT is MidsommerFlight’s perennial production, directors are rotated to offer a range of conceptual approaches to the comedy. This year’s Director, Bex Ehrmann (they/them) is queering up the Bard with a cast of diverse, trans and non-binary actors of various and sundry genders, races [albeit all human], and body types. Jack Morsovillo (he/him/his) is the Musical Director.
The basic plot is (relatively, for Old Will) simple: twins Viola and Sebastian are separated when their ship is wrecked. Then as ever, it’s hard for women to find a good job, so Viola undergoes non-surgical gender reaffirmation, renames herself Cesario and is hired by bluff and blustering Orsino to woo the Lady Olivia on his behalf. Lady Olivia contrarily falls for Cesario, (who is Viola in disguise), who in turn pines for Orsino … Oy! Hilarious antics unfold.
Every member of the MidsommerFlight troupe is a superb actor, dancer, and singer, and the cast of TWELFTH NIGHT is extensive. The cast is authentic and features an incredible amount of talent - Rusty Allen (he/him/his, Malvolio), Laurel S. Barrett (she/her/hers, Antonia), John Drea (he/him/his, Orsino), Becca Duff (she/her/hers, Fabian, U/S Feste), Courtney Feiler (she/her/hers, Valentine/Officer/Musician, U/S Olivia), Caleb Gibson (he/him/his, swing, u/s Orsino, Antonio, Sir Toby), Rae Hamilton-Vargo (they/them/theirs, Sebastian, u/s Malvolio), Reginald Hemphill (he/him/his, Sir Toby Belch), North Rory Homewood (he/him/his, Feste), Jessica Love (she/her/hers, Maria), Ebby Offord* (she/they, Olivia), Victoria Olivier (she/her/hers, swing, u/s Viola, u/s Sir Andrew, u/s Sea Captain/Priest/Musician, u/s Curio/Valentine/Officer/Musician), Travis Shanahan (he/him/his, Sir Andrew Aguecheek), Maddy Shilts (they/he, Viola/Cesario), Noelle Simpson (they/them/theirs, swing, u/s Sebastian, Curio, Valentine, Officer, Musician, u/s Sebastian), Natalie Welber (she/her/hers, Sea Captain/Priest/Musician, u/s Maria and Fabian).
The crew is just as superb. Text Captain Bobby Bowman (he/his) makes iambic pentameter accessible to ears still ringing from Janis, Jimi, and Mick, and further manages to enact the story despite ejaculations like “But soft!” As ever with Shakespeare, the tasks of Fight and Intimacy Directors Thomas Russell (he/his), (Fight), and Charlie Baker (he/they), (Intimacy) tend to overlap.
Cindy Moon (she/her) does a terrific job with costumes, and the music, composed by Elizabeth Rentfro and Alex Mauney, with additional composition by Music Director Jack Morsovillo along with Becca Duff, Courtney Feiler, North Rory Homewood, Victoria Olivier, McKell Rae, Noelle Simpson, and Natalie Welber is a delight – flutes and lutes and mandolins, oh my! Alyssa Mohn (she/her) (Scenic and Props), exploits the wondrous backdrop of the Chicago Conservatory.
TWELFTH NIGHT is being performed Thursdays-Sundays through December 18th at the Lincoln Park Conservatory (2391 North Stockton Drive, Chicago). For tickets, performance times and more show information click here.
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