Jamie sings John Dale, the poignant story of a street painter who paints the portrait of an elusive lady. Michael Smith introduced the song to us. . Here she honors her late a partner on the 3rd anniversary of his passing. Accompanied by John Erickson.


The evening is presented dinner-theater style starting at 7 PM, with Chief’s offering its extensive menu and drinks.  This two-set show begins at 8:00 PM.

Jamie will be joined by John Erickson piano, daughters Meg Broz and Nia O’Reilly-Amandes singing harmonies, and Judi Cogan Heikes – who co-hosts the event.

Read the full press release: https://www.jamieoreilly.com/jamie-oreilly-legacy-cd-release-heritage-bake-sale-at-chief-oneills-pub/

A highlight of the evening will be the Heritage Bake Sale & Raffle, featuring baked goods from home cooks created from treasured family recipes gathered from the community. The Great American Baking Show finalist Sarah Chang (@onweekendswebake on Insta) and esteemed food writer, cook and photographer Monica Rogers (https://www.mkrogersfoodbeauty.com/) will contribute premium bakes to a Raffle.
Read my blog about Monica here: https://www.jamieoreilly.com/meet-monica-kass-rogers-heritage-bake-sale-premier-baker/
Other raffle prizes include restaurant gift certificates, and an Irish tea time gift basket.  Buy $20 raffle tickets here: https://www.jamieoreilly.com/legacy-project-heritage-bake-sale-raffle/
Listen to Jamie sing Annie Laurie

Listen to Jamie sing White Cliffs of Dover

$30.00 admission*. Purchase advance tickets via Zelle: jamiejoanoreilly@gmail.com
(OR) *PayPal via the button below *includes $2.50 handling charge.

Note: O’Reilly family receives $10 off admission. $20 tickets.  For Zelle use jamiejoanoreilly@gmail.com  

Make it easy and fill out the ticket/donor form here: Purchase using PayPal Donor form (add $2.50 handling fee).

Paying by check? download the order form.
Ticket order form


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. (johnericksonpiano.com) 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.


Join Us Downtown Chicago for a Very Special Evening!
Tough Broads & Tender Lasses: Songs of Resilience
With Jamie O’Reilly, vocals
And John Erickson, piano
with Judi Cogan Heikes, narration

Thursday, March 23
The Cliff Dwellers
200 S. Michigan Ave 22nd Floor
Chicago, IL 60604
RSVP to Sally Farmer reservations@cliff-chicago.org
or call (312) 922-8080

Cash Bar: opens at 5:00 PM. Dinner: 6:00 PM. Program: 7:15 PM.
Dinner & program: $48, Program only (limited seating): $20
Parking at 17 E. Adams (discounted with coupon held at the bar).

Vocalist Jamie O’Reilly pays honor to the 20th century chanteuse — women who met adversity and struggle with tenacity and vigor — leaving behind classic songs and rich stories. These are women who weathered the stormy entertainment world with determination and vivacity, surviving world wars, poverty, and personal loss. (Among this group is Judy Garland, Mahalia Jackson, Sophie Tucker, Jeanette MacDonald, Ella Fitzgerald, Edith Piaf, Vera Lynn and Joan Baez).

We’ll hear songs our mothers sang to us; radio hits played during the war years; songs from old movie classics, and tunes widely sung in parlors, music halls, cabarets, and around the dinner table. Also featured are some of the signature songs Jamie wrote with her late partner, Michael Smith, for their critically celebrated theater productions and recordings. Lyrical jazz pianist John Erickson will accompany Jamie on this captivating musical journey in splendid celebration of Women’s History Month.

Listen to Jamie sing Sophie Tucker’s Blue River