Cassandra Kaczor

Chicago, IL

$300-$1200

Travels up to 120 miles

Get a free quick quote
Promotional video thumbnail 1 for Cassandra Kaczor

Jumpstarted (Jukebox the Ghost Cover)

Promotional video thumbnail 2 for Cassandra Kaczor

Tennesee Whiskey (Chris Stapleton Cover)

Promotional video thumbnail 3 for Cassandra Kaczor

Many the Miles (Sara Bareilles Cover)

Promotional video thumbnail 4 for Cassandra Kaczor

Put Your Records On (Corinne Bailey Rae Cover)

Promotional video thumbnail 5 for Cassandra Kaczor

Dueling Pianos in Downtown Chicago

Gallery photo 1 of Cassandra Kaczor
Gallery photo 2 of Cassandra Kaczor
Gallery photo 3 of Cassandra Kaczor
Gallery photo 4 of Cassandra Kaczor
Gallery photo 5 of Cassandra Kaczor
Gallery photo 6 of Cassandra Kaczor

Picture by Jacob Floyd Photography

Overview

I can take requests for and perform over 1000 songs on the spot! From birthday parties to corporate events, or any sort of get-together, casual or formal, I would love to entertain your guests. Guests may write down or verbally suggest their favorite song, and I will sing it, play it, and encourage everyone to sing along! I can perform in most genres: pop, rock, country, blues, classical, musical theatre and even hip-hop! Every performance and event is entirely unique, tailored specifically to your guests' musical preferences. I bring the gear and the party to YOU!

I also hold a master's in music and can perform any type of music (such as classical) at more formal events such as weddings.


Reviews

4 reviews

Small thumbnail image for reviewer Tim W.

Tim W.

June 17, 2025

Huge hit outside at Bacino’s Grill at Diversey Driving Range

Cassandra just started playing on Tuesdays outside in Lincoln Park at Bacino’s Grill, and the lawn filled up quickly. Cassandra was talking requests and singing covers that pulled so many dog-walkers, cyclists and neighbors to pull up an open lawn chair and order a beer. It was amazing and fun. So glad she is a regular on Tuesdays at Bacino’s Grill and now a regular musician at Amasa Eatery every Thursday (amazing Food Truck) just steps south along the Harbor path). Cassandra is making summer way more fun!

Hired as: Keyboard Player, Singing Pianist


Small thumbnail image for reviewer Jacob P.

Jacob P.

February 25, 2025

One of the best in the business

I’ve had the pleasure of seeing Cassandra perform for years. Her showmanship is uncanny, being able to rapidly read an audience and change the show to better suit them.

With an amazing voice and some of the most diverse playing styles I’ve seen in a long time, one can expect any variety from rock and boogie woogie to classical and jazz. Rarely does a talent like Cassandra come around and anyone would be lucky to have her as a performer.

Hired as: Singing Pianist


Small thumbnail image for reviewer Alex D.

Alex D.

February 24, 2025

A Phenomenal Talent Who Creates Unforgettable Experiences

We’ve had Cassandra perform at our Christmas parties multiple years, and she is nothing short of extraordinary. Her talent as both a pianist and vocalist is unmatched, and her ability to play virtually any song on request keeps the energy high and the crowd engaged. She doesn’t just perform—she creates an experience, making each event feel personal and unforgettable. Our friends still talk about those nights because of the atmosphere she helped create.

Beyond her talent, Cassandra is a joy to work with in the planning process—she is personable, responsive, and incredibly accommodating when coordinating event details. From selecting the perfect setlist to working through logistics, she communicates seamlessly and ensures everything is set up for a great performance. If you’re looking for someone to elevate your event with incredible music and an engaging presence, Cassandra is the one to book.

Hired as: Singing Pianist


Small thumbnail image for reviewer Thomas S.

Thomas S.

February 19, 2025

Professional and Fantastic

Cassandra has done work for me over the years and is always professional, on time, courteous and a wonderful performer. She is thoughtful and is a team player. I always know Cassandra is going to hit a home run.

Hired as: Singing Pianist

Write a review

Booking information

Price range: $300-$1200

Languages: English

Gig length: 60 - 240 minutes

What to expect

I am enthusiastic and qualified to perform at the following: weddings, birthday parties, corporate events, college/student events, bars/music venue events, and many more! Because I have a master's in music, I can perform your wedding ceremony music, then turn around and put on an all-request rock and roll piano show at the reception!

The great part about hiring an all-request entertainer is that no event is exactly the same. The clients and their guests pick the songs and the artists or make special dedications, and I encourage everyone to sing and dance along!

I also have a full gear setup, so the party comes to YOU, no hassle, no additional support needed!

About

Cassandra Kaczor is a Chicago-based composer, pianist, singer, multimedia artist, multi-instrumentalist, and entertainer. She has performed piano, drums, bass, and as a vocalist in nineteen states, on cruise ships, and in Europe. She obtained her master's in music in 2017 from Roosevelt University's Chicago College of Performing Arts.

Cassandra works as a professional piano bar entertainer with a catalogue of over 1000 songs that guests can request on the spot.

She lives in Northwest Chicago with her husband is currently pursuing a second master's in Clinical Mental Health Counseling.

Additional booking notes

I have a Yamaha keyboard, mics and keyboard stands, a bench, a mixer, cables, and two JBL speakers that can fill any room with full sound!

Set list

I know over 1000 songs across genres. If you are looking for specific songs or artists ("must-plays", if you will) and I do not know them, I will learn them for your event at no extra charge!

Influences and inspiration

I am comfortable performing artists from Sinatra and the Beatles to Dr. Dre and Taylor Swift. I do not discriminate by genre! Country, pop, rock, blues, R&B, hip-hop, and classical music are all within my wheelhouse.

Setup requirements

Outlets

Check out these featured profiles

Matt Griffo

4.97 (72)
Top Performer
121 Verified bookings

  • Chicago, IL
  • Singing Pianist
  • $100 - $1,500

Frank C. said “Matt is versatile, not only able to handle almost any music request, but also an accomplished ukulele player. He's always able to any situation that comes up ”
Featured

Rachel Bachman

5.0 (72)
Top Performer
106 Verified bookings

  • Chicago, IL
  • Singing Guitarist
  • $200-$2500

Kaitlynn R. said “I live six plus hours one way from my sister. I wanted to send her some cheer. She is a Swiftie. I booked on Gig Salad which is easy. Rachel Bachman is a star. Everyone who has seen the joy on my... ”
Featured

Sarah Lightman

4.96 (75)
Top Performer
45 Verified bookings

  • Miami, FL
  • Singing Guitarist
  • $999-4,999

Nicole K. said “Sarah was hired for an outdoor cocktail party. We had a beautiful, comfortable venue for our guests that required a cool vibe from a musician. Sarah provided that! Her voice and song choices were... ”

Carl on Keys

5.0 (6)
Top Performer
6 Verified bookings

  • Lisle, IL
  • Singing Pianist
  • $150 and up

Jessica D. said “Carl was professional, fun and entertaining for our holiday party! He sang a variety of songs and mixed in a bunch of fun Christmas songs. He brought microphones and shakers so we could sing and... ”