Theatreworks Chicago Tour

Chicago Tour - October 2023

Introducing: Theatreworks Chicago Tour

October 12-16, 2023

Theatreworks has long taken an annual trip to London to share the joy of travel with our patrons, and to explore the exciting theatre offerings in a different city. That tour yields artistic inspiration, fellowship, and relationship building, and while the London trip will continue for years to come, we're excited to introduce a more accesible theatre tour, a little closer to home, in the Windy City: Chicago! Spend a long weekend with the Theatreworks team, and come see the cutting edge American work Chicago has to offer. 

Chicago theatre is famous for two specific styles-- in the 1970s, theatres like Steppenwolf produced a major style of American realism with playwrights like Sam Shepard and David Mamet, and actors, like the famous ensemble at Steppenwolf itself-- John Malkovich, Joan Allen, and Gary Sinise. Then in the 2000s, Chicago premiered high physical theatre from companies likes Lookingglass and the Neo-Futurists. Throughout, it is Chicago's theatre storefront ecosystem, where smaller companies perform in former storefronts, that have proven to be a major incubator for artists and new work. Chicago is also a wonderful city for lovers of art and architecture city! With the Art Institute, the Museum of Contemporary Art, Frank Lloyd Wright's studio, and waterfront architecture tours, there are amazing visual art opportunities in the city as well.

Your $1750 registration includes*:

  • 4 nights accommodation at the Millenium Knickerbocker Hotel. Just off the Magnificent Mile, the hotel offers easy access to many attractions, including several major theaters. 
  • Tickets to 4 shows (titles below) at some of Chicago's most iconic venues. 
  • Morning meetings to discuss the plays and Chicago's theatrical landscape with other travelers, lead by Theatreworks Artistic Director Caitlin Lowans. 
  • A $500 contribution to Theatreworks (along with our boundless gratitude and an “arts patron” line for your resume).

 Ready to join us?

Secure Your Spot Today!

If you have other questions about the tour, please reach out to Lily DiSilverio or stay tuned for an information session coming in June!

Email Lily DiSilverio

*To accommodate individual preferences for travel, please note your airfare is SEPARATE from your tour registration. $875 is due at registration to secure your space, with full payment due September 15. 

Your Host

  • Caitlin Lowans (Theatreworks Artistic Director)

    Caitlin Lowans

    Caitlin Lowans is a theatre director, arts educator and community-builder, currently serving as the Artistic Director at Theatreworks Colorado Springs, the professional theatre in residence at the University of Colorado Colorado Springs. Prior to Theatreworks, Caitlin came from Chicago, completing coursework for their MFA in Directing at Northwestern University, with thesis currently in process (yes, Mom, it will get done!). Prior to Northwestern, Caitlin served as the Associate Artistic Director and Director of Education at Greater Boston Stage Company (formerly Stoneham Theatre), an Equity Theatre north of Boston, as well as freelance director, teaching artist, and dramaturg in New England.

Your Shows

  • By Martyna Majok, Directed by Steph Paul 

    From the Tony award winning company that developed August: Osage County, and launched countless Broadway transfers along with the careers of luminaries like Tracy Letts, Laurie Metclaf, and Gary Sinise, comes a new play by Pulitzer Prize Winner Martyna Majok. Newark, NJ. Post-9/11. Two teenagers, brought to America as children, now face an unlikely foe: unexpected, unreciprocated love. Their friendship is no longer enough (for one of them) and their adopted country doesn’t love them back. Majok brings light to the sacrifices made by DREAMers, lovers and life-long friends in the heartbreaking and hopeful Sanctuary City.

  • By Pearl CleageDirected by Lili-Anne Brown

    Chicago's oldest and largest non-profit theatre (with a history of major transfers, and a regional Tony to it's name) mounts a new work by one of America's sharpest theatrical voices. Every year since Emancipation, The Nacirema Society of Montgomery, Alabama introduces six elegant African-American debutantes to a world of wealth, privilege and social responsibility. For these young ladies, bus boycotts and freedom marches are less interesting than making a perfect entrance—or plotting the perfect blackmail. As the Society celebrates its centennial…with young love brewing, old flames simmering and national media attention abounding…what would dare go awry?

  • By Stefano Massini, Directed by Nick Bowling and Vanessa Stalling

    Winner of the 2022 Tony Award for Best Play, The Lehman Trilogy weaves together nearly two centuries of family history in an epic theatrical event charting the humble beginnings, outrageous successes, and devastating failure of the financial institution that would ultimately bring the global economy to its knees. Told in three parts over one evening, The Lehman Trilogy is the quintessential story of western capitalism, rendered through the lens of a single immigrant family.

  • By Lucille Fletcher, Directed by Georgette Verdin

    What’s more nightmarish: not being able to trust those around you… or not being able to trust yourself? Moonlit streets, a restless mind and a large window have become Elaine’s nightly routine in her luxurious city townhouse. But insomnia is the least of her worries when a dead body appears in the window of an abandoned, squalid unit across the street. To make matters worse, the body disappears before her husband, best friend or maid have a chance to witness the atrocity. This suspenseful revival is filled to the brim with tricks and twists, leaving audiences on a psychological rollercoaster until the very. last. second.

Can't wait to come aboard? We would absolutely love to have you. Register below! More questions? Reach out to Lily DiSilverio ( to learn more about the tour.

I'm Ready to Join the Tour!