About Last Weekend

Coming home, singing Sondheim, and thinking about my Dad

Jun 19, 2025

Hello Friends,

Greetings from 30,000 feet above... somewhere. I’m on my way to Los Angeles and gave myself this flight as a deadline to write about last weekend—a homecoming I’ll never forget.

I actually wrote a “shitty first draft” to send out last week in advance of my trip to Chicago, but decided to bless and release it—and spend that time enjoying being back in my hometown.
And what a weekend it was.

It Wasn’t a Gig—It Was an Event

A little background on how this came to be: I had been wanting to bring this show to Chicago for quite some time. I’ve done it so many places—including New York, Los Angeles, San Francisco, The Kennedy Center, London, and Madrid—but somehow never in my hometown.

I knew my friend Seth Rudetsky had been performing in Chicago, so I asked if he had any venue suggestions. He told me to get in touch with Brian Maschka, who had produced his recent concerts at the Studebaker Theater. I called Brian, we had a great talk—and he said he’d be happy to produce my return to Chicago.

The Studebaker is a gorgeous 600-seat theater. I’d been thinking more like a 200-seater—could we really fill a place that big? Brian thought we could. So I bet on myself.
Doing this show in that historic theater turned what was a gig into an event. Thank you, Brian!

What made it extra-special is that my sister Ann flew out from Tucson for the concert! She hadn’t seen me do a solo show in person since she and Kari moved to Tucson seven years ago. I can’t tell you how much it meant to have them both there, cheering me on.

I was struggling to put into words what Saturday night meant to me, and then I read the Facebook post Ann wrote on her flight home. I asked if I could share it here, and she said yes.

Isn’t that beautiful? It made me weepy. As Ann said, it was so special to have so many friends and family in attendance. It actually felt like my wedding, almost 40 years ago!

At the end of my concert, I gave a shout-out to my friends from New Trier East High School and my pals from Marriott’s Great America theme park in Gurnee, IL—my first professional job—when I was 16 and still wearing braces. One of my solos back then? “Send in the Clowns!”

It was wonderful to have Dad’s friends and colleagues from WTTW at the show. He’s been on my mind so much lately—and being in Chicago on Father’s Day weekend made me miss him even more.

And I’m so grateful Nicholas could come to Chicago to sing “Move On” with me. When the song finished, he blew a kiss to his beloved Grandpoppy in heaven.

A Song for My Dad

Dad loved to sing, and his go-to song was “Embraceable You.”
This is for you, Dad.

I had a lot of press opportunities for this show—a testament to how beloved Dad is in this city—and it gave me the chance to talk about him more than I ever have before. Here’s an excerpt from an interview I did with Marc Vitale for WTTW. You can read the full interview here.

I also had the chance to do two TV interviews—something that doesn’t usually happen for a one-night concert! One on ABC-7 and includes some great clips, and the other was live on WGN, where I sang “Our Time” on two hours of sleep!

The one thing I didn’t get to do on this trip (which would have made it perfect) was sing at a Cubs game. My dad loved his Cubbies and always supported my love of the Mets. It was his dream to sing “Take Me Out to the Ballgame” during the seventh-inning stretch at Wrigley.
When he finally got the chance, in 2008, halfway through the game the skies opened—and the game was rained out.
Someday, I’ll finish what he wasn’t able to do. Mark my words.

Where in the World Is Liz?

I’m in Pasadena now, and so happy to be working with Michael Feinstein and Joshua Henry again at Saturday’s Pops concert. I have some very fun gigs coming up—including concerts in Lisbon! (I’ve never been, so any recommendations are welcome.)

Here’s where you’ll find me the next few months:

June 21 ARCADIA, CA Pasadena Pops with Maestro Michael Feinstein and Joshua Henry

June 26 FLUSHING, NY National Anthem New York Mets vs Atlanta Braves

June 28- July 3 TECATE, MEXICO Rancho La Puerta

July 10-12 LISBON, PORTUGAL Broadway in the Park, 2025 with Santino Fontana and Seth Rudetsky

July 19 WAINSCOTT, NY Broadway & Beyond

Sept 3-4 NEW YORK, NY The Wizard and I: Liz Callaway Sings Stephen Schwartz

CLICK HERE FOR MY FULL SCHEDULE

That’s it for this issue of Between Flights.

I’m grateful I can share these experiences with you. Thank you for reading!

xoxo, Liz

P.S. Thanks for the kind words and thoughtful responses to my last newsletter about seeing Johnny Mathis’s final live performance. I was very touched by how many of you shared your personal experiences with me. In case you missed that issue, you can read it here.