Chicago Theatre Tour

August 30 – September 4, 2023

Join us for four shows at iconic Chicago theaters and let us show you why the “Windy City” is such an important part of the American Theatre scene.

What are former travelers saying?

“So well organized! Great seats at all the shows!” 2022 Chicago Traveler


Trip Includes:

  • Round Trip airfare with American Airlines between Portland and Chicago
  • 5 nights stay at Omni Hotel in Downtown Chicago
  • Breakfast every day at the hotel
  • Dinner 3 of 5 evenings with wine included
  • Tickets to 4 Broadway quality productions from prominent Chicago theaters
  • Diamond Suite tickets to the White Sox vs Tigers game
  • $500 tax deductible donation to MSMT
  • Transfers to airport and theaters
  • Baggage handling at hotel
  • Fully Escorted by Artistic Director Curt Dale Clark, Managing Director Stephanie Dupal, and Development Director Morgan Rodgers
  • All taxes and gratuities for all services stated above

Per person trip fees:

  • $4,870 – Double Occupancy, one bed
  • $4,973 – Double Occupancy, two beds
  • $5,760 – Single Occupancy


Limited space available! Reserve your spot with a deposit of $500. For more details, please contact Morgan Rodgers at 207-725-0150 or




MJ The Musical – The National Tour at the Nederlander Theatre

The music. The showmanship. The icon. Now, the unparalleled artistry of the greatest entertainer of all time comes to Chicago as MJ, the Tony Award®-winning new musical centering on the making of the 1993 Dangerous World Tour, begins a tour of its own. Created by Tony Award®-winning Director/Choreographer Christopher Wheeldon and two-time Pulitzer Prize winner Lynn Nottage, MJ offers not just Michael Jackson’s singular moves and signature sound, but also a thrilling glimpse into the creative spirit and obsessive mind that created the biggest pop superstar the world has ever known.

Little Shop of Horrors– at Paramount Theatre

From the genius duo behind Aladdin, The Little Mermaid and Beauty and the Beast, comes the doo-wop R&B sensation Little Shop of Horrors. Join us on Skid Row as meek and mild Seymour Krelborn discovers a strange and unusual plant he names Audrey II – one that feeds on human blood. Seymour becomes caught up in a wild scheme of trying to acquire fresh blood for his carnivorous plant – all while attempting to save the love of his life from her evil dentist boyfriend. Little Shop of Horrors is a wild ride filled with some of the catchiest songs including “Suddenly Seymour” and “Suppertime.” But remember…DON’T FEED THE PLANTS!

Gypsy – at Marriott Lincolnshire Theatre

The mother of all musicals! Gypsy is the tale of the ultimate ambitious stage mother, fighting for her daughters’ success while secretly yearning for her own. Arthur Laurents’ landmark show explores the world of two-bit show business with brass, humor, heart, and sophistication. This lavish classic boasts a celebrated score by Jule Styne and Stephen Sondheim including: “Everything’s Coming Up Roses,” “Let Me Entertain You,” “Some People,” and “Together Wherever We Go.”

Personality: The Lloyd Price Musical – at Studebaker Theatre

From humble beginnings in his hometown of Kenner, Louisiana, Lloyd Price overcame incredible obstacles on his way to a revolutionary musical career. He became the first Black man to open a nightclub below Harlem in New York City, and the first recording artist of any color to create his own record label, generating more hits like “Stagger Lee” and “Personality,” and spreading the New Orleans R&B sound throughout the world.

White Sox vs Tigers – at Guaranteed Rate Park

Artistic Director Curt Dale Clark got his start in Chicago and many of you will know him to be die-hard White Sox fan, so this year we are adding a box at the game! We have a private Diamond Suite at the game, so even if you aren’t a huge baseball lover, come enjoy America’s pastime in style with one of the Sox biggest fans.