The Cliff Dwellers Presents
A St. Patrick’s Day Showcase
Jamie O’Reilly’s
In Old Chicago: Stories & Songs of a Beloved City
Thurs March 14 at 6 PM
The Cliff Dwellers Arts Club
200 S Michigan Ave  22nd Floor
Chicago, Il.
Ph (312) 922-8080;

Listen to a sample here, Tex joins up

Listen to Annie Laurie

March 14, 2024
In Old Chicago: Stories and Songs of a Beloved City
Jamie O’Reilly & Friends

Part memoir & part concert, this program captures an explosive time in Chicago history as a great city comes of age. It grew out of an extensively researched legacy project by singer /writer Jamie O’Reilly of her Irish-American family and their 120-year roots in Chicago.

Heard on the WFMT Midnight Special 70th Anniversary Broadcast in spring of 2023, In Old Chicago will feature actors Christopher O’Reilly, Judi Cogan Heikes and Victor Holstein reading poetry and excerpts from family memoirs that recall Chicago, from the turn of the 20th century into the outbreak of WWI and the early 20s: the newspapers, the neighborhoods, the union halls, activism, and the arts.

Songs of the era, performed by Jamie in turn-of-the century style, include stirring anthems, ballads, and sing-a-longs, with fine accompaniment by pianist John Erickson. We’ll also hear some favorite songs of the late Studs Terkel, i.e., Annie Laurie and His Eye is on the Sparrow (the signature song of Mahalia Jackson). This program also features two stirring videos illustrating the songs. Among these, “Sanctuary City,” celebrates Chicago’s immigrant history and includes photos from the community.

Here is a fine way to celebrate both St. Patty’s Day and Women’s History Month.


Watch the “Aunt Dorothy” video here:


Jamie O’Reilly hosts the Heritage Bake Sale & Raffle at Chief O’Neill’s Pub. A one-night only event, featuring baked goods from home cooks created from treasured family recipes gathered from Roots Salon community. Hosted by Judi Heikes and Jamie O’Reilly, the bake sale will take place at Chief O’Neill’s Pub during her Legacy Concert event. Offering homemade foodstuffs for sale to take-home. We will also offer several premium items in a Raffle!

Jamie O’Reilly & Co bring In Old Chicago: Stories and Songs of a Beloved City” to Stage Left Cafe in historic Woodstock, Illinois —Hosted by Off Square Music. And the Woodstock Folk Festival.

ENSEMBLE (pictured here with Marilyn Rae Beyer)
John Erickson, piano. Jamie O’Reilly,  Judi Cogan Heikes, Christopher O’Reilly and Victor Holstein.

Off Square ticket link:

When & Where
Off Square On Air Series
July 7 @ 7:00 pm – 9:00 pm CDT
Doors open at 6:30 PM
Zoom Sign-in at 6:45
Stage Left Cafe
125 W Van  Buren St.
Woodstock Il

This is a hybrid show. Off Square On Air brings you a unique concert/interview in this fourth show in the series. Choose to be there – live at Stage Left Cafe or watch on Zoom.

In Old Chicago — part memoir, part concert — is the work of singer/writer Jamie O’Reilly and captures an explosive time in Chicago history as a great city comes of age. Through stories and songs, she shares the roots of a vocal tradition and rich history of her Irish American family, who have been in Chicago for over 120 years, and how that tradition led to the singer/activist she is today.

Recently featured on the WFMT Midnight Special 70th Anniversary Broadcast, In Old Chicago also features Christopher O’Reilly, Judi Cogan Heikes and Victor Holstein reading poetry and excerpts from family memoirs of Chicago from the turn of the 20th century into the outbreak of WWI and the early 20s: the newspapers, the neighborhoods, the union halls, activism, and the arts. And more.

This is a Preview of this Year’s Woodstock Folk Festival
In Old Chicago previews the upcoming July 16 Woodstock Folk Festival. Off Square On Air is brought to you by Off Square Music and the Woodstock Opera House.

Off Square On Air
is a series of two-hour concert/interview shows. In this fourth event in the series, Jamie and her group bring us  music, history and stories. Before the concert, they chat with the host about the show and the Voices of Old Chicago Legacy Project.  The live audience is invited adding to the experience with their own questions, comments, and stories.  Zoom attendees are invited to join as well via chat.

Attend at Stage Left. Tickets are $15.00/pp to attend in person at Stage Left Cafe.

Attend via Zoom. You can also enjoy the concert from home! Tickets are $10.00/pp to attend via Zoom. Get your Zoom tickets below. (Zoom tickets must be purchased no later than one day in advance in order to receive the Zoom link via email on time.)

Watch the video SANCTUARY CITY

Watch the Video  She Would Sing the Kerry Dances

TESTIMONIALS: What People Say…
“Jamie is especially gifted, with her vibrant voice and a passion for life.” ~ Studs Terkel

“Jamie O’Reilly brought such lilting beauty to our Bloomsday Chicago at Chief O’Neill’s, her captivating voice perfectly capturing mood and tone throughout our evening. Her voice was as lambent light across and even through the very words of our play, a gift of whimsy and romance, a reflection on love and loss, a perfect complement to our take on James Joyce’s grand story.” ~ JR Sullivan, Theatre Director/Writer/Producer

“It moves me every time I hear you…She’s one of a kind, ladies and gentlemen. One of a kind.” ~ Rick Kogan, WGN Radio 720

“Jamie not only has the voice of an angel, but possesses an adventurous spirit that allows her to create shows and moments and memories that are real and lasting…She is a Chicago treasure.” ~ Rick Kogan
WGN Radio, Chicago Tribune

“Together their musical palette is pretty astonishing.” ~ Chicago Magazine

“Your voice was gifted to you but then your soulful spirit took it deeper. Some sing the notes, some take those notes and it becomes MUSIC. When you sing, your voice is pure, bell-like. You bring your story to your audience, phrasing each lyric with a genuine delivery.“ ~ a fan

With her distinctive lilting voice and broad vocal range, Jamie O’Reilly approaches folk music with the passion of a theater artist and the attention of an art song interpreter. Her programs include songs reminiscent of by-gone eras, traditional, and original work in the singer/songwriter genre. Vocal selections range from romantic standards from the 1920s – 40s, to sultry ballads and Celtic folksongs, to arts songs and parlor songs, contemporary folk, and Americana ballads. She is accompanied by the finest musicians on guitars, piano and more.

Jamie is accompanied at Off Square by the pianist John Erickson. ( While creating new work on a regular bass, Jamie’s programs also revisit the songs she sang when she was coming up as a young professional and throughout her 40-plus year career as a ballad singer; those she performed on radio, for concerts, tributes, and in cultural arts series throughout the Chicago area. Programs heard at the Chicago Cultural Center, the Poetry Foundation, the Chicago Humanities Festival, and myriad arts venues. She specializes in period pieces — music for the centenary of the 1893 World Columbian Exposition, Irish Vaudeville, European-style cabaret and songs from the folk canon. Highlights from the award-winning musical revue Hello Dali: From the Sublime to the Surreal, created with Michael Smith, are also included in Jamie’s programs.