In Old Chicago: Stories & Songs of a Beloved City

A Note from Producer/Writer Jamie O’Reilly
Sept 2023
This page features updates on this growing, exciting production,
In Old Chicago, which is part of my Voices of Old Chicago Legacy Project.
For updated information on videos, recordings, events and historical background,
please visit my BLOG and EVENT pages on this website. Listen to my songs interspersed here as well. Read my latest Enewsletter.
Jamie O’Reilly
for In Old Chicago

Sept 21 Event at Chief O’Neill’s Pub
CD Release of two-album set, Legacy and In Old Chicago

Read more:

Past Performance Friday, July 7, 2023
Jamie O’Reilly’s IN OLD CHICAGO
with John Erickson, piano & Ensemble
Stage Left Cafe – in the Woodstock Opera House
125 W Van Buren
Woodstock, Il
Preceded by a live interview with the ensemble

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

Special hybrid show! Off Square On Air offers a unique experience live at Stage Left Cafe or watch on Zoom, with an interview with the performers before the show. *Doors open at 6:30 PM. Zoom Sign-in at 6:45 PM.

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. Songs of the era are performed in turn-of-the century style including stirring anthems, ballads, and sing-a-longs. Jamie also sings songs by Michael P. Smith and Anne Hills.

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.

Click here for tickets for In Old Chicago in Historic Woodstock, hosted by Off Square Music!


Watch our two stirring videos, produced this winter:
Sanctuary City video

She Would Sing the Kerry Dances here:

Listen to my Rick Kogan WGN interview on my blog here.

Dorothy O’Reilly

“It was not a pretentious house nor was it furnished in grand style but it was comfortable and warm with love and happiness. The south parlor led into a large kitchen dining room which was the heart of the whole place.”

Memoir, Dorothy (Dottie) O’Reilly

In Old Chicago brings songs and stories of Chicago’s vibrant early 20th century history — Its people and neighborhoods, rich with arts and culture. Feisty activists. Family lore. Period songs and poetry by one of Chicago’s most treasured artists.

In her program In Old Chicago, singer/writer Jamie O’Reilly 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.

“THANK YOU!!! That was an absolutely beautiful, inspiring, instructive, fun show in which to participate. So much great music, readings, poems, Chicago local history and family experiences. It was a wonderful experience – that we will recall and discuss for the rest of our lives, and will be passed on to our families. We hope you will do it again locally, so our family members and friends will be blest with this experience.”

Chuck Ripp, Oak Park, IL commenting on In Old Chicago
Listen to Love’s Sweet Song

Jamie sings accompanied by John Erickson on WFMT’s grand piano

The program celebrates Chicago’s vibrant history and her connection to it, as she reflects on forty-five years in a beloved city, with tales of its neighborhoods, and stories of her Irish and German ancestors and other immigrant groups: artists, writers, and feisty activists around the turn-of-the last century, into and following the first world war.

Jamie debuted the In Old Chicago program in October, 2019 at Chief O’Neill’s glorious pub in Chicago, to a full house and standing ovation. In fall of 2021 and again in 2022, with pandemic challenges, Jamie and Company returned with revised versions of the In Old Chicago program. She is accompanied in the live presentations by gifted pianist John Erickson. Judi Cogan Heikes, Christopher O’Reilly and Victor Holstein provide narration and read poetry.

Jamie at Chief O’Neill’s Pub, Albany Park


Bring Voices of Old Chicago as a Legacy program to community venues. Contribute YOUR old photos to our multimedia project! Contact Jamie to schedule an event in your community. Email:; Text 773.203.7661

Jamie, whose expansive voice can navigate a wide range of musical genres and styles, embodies the vocal tradition of her ancestry in lush interpretation of songs; from the front parlor to chamber concert repertoire; from vaudeville and music hall stages. Songs showcase Jamie’s signature soprano in songbird-style ballads, romantic standards, sultry gypsy ballads, parlor songs, Americana ballads, and Irish songs. There are also songs written for her by late musical partner, esteemed songwriter Michael P. Smith (Grapes of Wrath, Steppenwolf).

Listen to Jamie sing Sanctuary City
Listen to Jamie sing Annie Laurie

Nell O’Reilly Tucker at the Socialist Convention, 1907

Published memoirs, and poetry from Edward (Tex) O’Reilly, Irwin St. John (Friar Tuck) Tucker, Ellen (Nell) O’Reilly Tucker, Mame O’Reilly and Dorothy O’Reilly provide a substantial part of the text in the program. Integral to the piece is the role that radio played in her career, and a bit of lore from and about Studs Terkel (a friend of Jamie’s), the truest voice for a by-gone era.

Chicago’s connection to the Celtic Revival, initiated here by the 1893 World Columbian Exposition and the Irish Literary Renaissance, is a fascinating time, with international demand for Irish Home Rule and the emergence of many Irish artists on the world stage. Among them: the über gifted Yeats family, provocative Lady Gregory, and masterful James Joyce, (whose seminal novel Ulysses celebrated its centenary last June). As the Industrial Revolution took hold, the eight-hour day was furiously fought-for, and a heretofore unseen number of immigrants arrived, the humanities and intellectualism were alive and thriving in Chicago. The new Art Institute of Chicago acquired its masterpieces, grand museums were built, and lakefront parks were created.

Nell, Mary Ann, Mame (front) Tex, James (back)
Humboldt Park, early 1900s

Jamie’s ancestors were feisty activists, writers and artists. Great Uncle Tex, Great Uncle Tuck cousins Ernest, Dan and Ernie Tucker and Great Aunt Nell all wrote for newspapers. The Chicago newspapers — from the Inter-Ocean to the Chicago Tribune — for over 100 years.

Tex and Nell

Tex is the subject of the Lowell Thomas’s biography The Greatest Living Soldier of Fortune. Tuck and Nell contributed to poetry columns (Tribune’s Line-o-Type among them). Nell attended the School of the Art Institute. Tex fought in foreign wars. Jamie’s aunts Mame and Dottie taught in public schools. They participated in the Hobo College (offering classes to migratory workers), and Bughouse Square (with its soapboxers). They joined the Dil Pickle Club, a social club for arts, crafts, literature, and science, shared rituals with the Winnebago Tribe, attended Socialist gatherings, and organized for the Chicago Federation of Labor, and the Chicago Federation of Teachers as Chicago became a union town.

And they all sang — hosting salons where music, poetry, politics and philosophy merged in spirited gatherings. These traditions and events inspired Roots Salon, which Jamie established in 1993. Jamie’s aunts, uncles, parents and siblings (her late father James O’Reilly was a respected classical actor at Court Theater and Body Politic Theater) have contributed to the Chicago music and theater scene for over 95 years. Now the sixth generation of O’Reillys is part of the cultural landscape of Chicago: Jamie is a grandmother of three.

CARRY IT ON! What will you leave behind?
What stories, heirlooms and artifacts are part of your family legacy!
It’s long been thought the folksinger is a storyteller, as the troubadour once carried the tales of people and place, now we, the silver-haired, grace the audience with our songs and stories. Jamie’s current Legacy Programs are “In Old Chicago,” Roots Salon, and the Voices of Old Chicago Multimedia Project.
How do you explore your roots and family history – the music and stories, heirlooms and artifacts – and integrate them in your art. Create YOUR legacy? In Old Chicago Legacy Programs include our performance, followed by a talk and audience discussion.

“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 a 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, Director 2022, Bloomsday Chicago 


“A Voice for the Soul of the City”
Performer, writer, producer, cultural activist, historian

Many titles in the arts nomenclature can be assigned to Jamie O’Reilly.  It is her love of singing, an expansive creative spirit, and a fiercely held belief in the value of the artist in community that fuel her active and vibrant world.

With her distinctive lilting voice and broad vocal range, Jamie 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 gypsy ballads and celtic folksongs, to parlor songs and Americana ballads.  She is accompanied by the finest musicians on guitars, piano and more.

poster for Tough Broads & Tender Lasses

As a theater and music producer, Jamie is known for the powerful productions she brings to the stage, and the projects she brings to the recording studio, among these are Pasiones: Songs of the Spanish Civil War, and the award-winning Hello Dali: From the Sublime to the Surreal, a box office hit during the 2001 Victory Gardens Theater’s Tony-Award winning season.  Other celebrated programs include Songs of the Kerry Madwoman, which sets the poetry of Patricia Monaghan. The Gift of the Magi, performed with WGN Radio Host Rick Kogan, has been a highlight. 

In Old Chicago, researched, written and performed by Jamie, features songs and stories celebrating the culture of Chicago during the Arts Revival of pre-WWI Chicago, highlighting family history, local lore of Chicago neighborhoods and its connection to Dublin and Paris, and other vibrant cities.

Roots in the Garden, Tre Kronor, North Park

In 2021, Jamie produced the Roots in the Garden Series during the pandemic. In 2022, she produced Tough Broads & Tender Lasses: Songs of Resilience. She hosts a Storytime for Children at the Sweden Shop. This fall brought an indoor Salon Series to local treasure Tre Kronor Restaurant. 

As A Voice for the Soul of the City, Jamie’s work includes essays, stories, poetry and memoir, and pieces further exploring the range of the artist’s voice in community.  Jamie is known for her moving essays and creative writing on her Blog. Her frank and personal reflections focus on what inspires and challenges her as an artist and activist.  And how we make our way in the rapidly shifting cultural landscape 

Musical/Theatrical Programs about Chicago history are among Jamie’s specialties. She has created programs with historic themes including Irish American Vaudeville and Music Hall (Irish American Heritage Center), the 1893 World Columbian Exposition and Irish Pavilion
(for Smart Museum, Chicago Cultural Center), the Irish famine (Facing History), and Pasiones: Songs of the Spanish Civil War, the much celebrated folk cabaret, honoring the Abraham Lincoln Brigade.

Pasiones: Songs of the Spanish Civil War,
a favorite of Studs Terkel

In 1990, she co-created the original work A Season and a Time (the preview to In Old Chicago) for the A City Comes of Age Series for the Chicago Historical Society (Chicago History Museum). The rich and lively world of her Irish ancestors and the working immigrant experience, pre-WWI through WWII, continue to provide the landscape for In Old Chicago.

Jamie O’Reilly’s Roots Salon began in 1993 with a performance series hosted by Jamie and brother Beau, answering the need of Chicago artists seeking an intimate venue. Located in Jamie’s home, events at Roots were word-of-mouth happenings presenting music, visual art, poetry and theater. Jamie expanded her role as the Salonnière for the Roots Salons hosting neighborhood caroling at Christmas, a monthly women’s salon, membership events that included a master speaker series, and Rootsfest, a summer music festival.

Recommended links
Recent Article
“Singer Jamie O’Reilly is hosting a children’s story time this weekend

 — but the real story has been her life.”  – Rick Kogan, Chicago Tribune 10/11/22

 —Video Roots in Ireland

 —Blog SongNotes Mame’s White Fire Letter

 —Blog In Old Chicago Program

 —Blog Halcyon Days Songs in the Parlor,  Jamie Revives a Vocal Tradition

 —Blog In Old Chicago reimagined: Jamie sings Love’s Old Sweet Song and other songs