Chicago Singing Waiters Dazzle

Chicago Singing Waiters dazzle at a Chicago Fundraiser

The Amazing Waiters had recent privilege to celebrate Greek Heritage here in Chicago, Illinois recently. Celebrating the Greek City of Tripoli, Greece, the organization gets together one time a year for its annual fundraiser and is always looking for fun and unique entertainment.


Chicago Singing Waiters entertained at a fundraiser for the people of Tripoli, Greece


The President and organizer of this year’s event, Dino, was excited to try to have us this year. “Last year, we tried to make it happen, but our singing waiters were so new in Chicago that we were unable to fulfill the request”, stated James Anest, General director of The Amazing Waiters. “So, we decided to table it until next year…sure enough, I pleased to receive a call from Dino asking if our Chicago Singing Waiters were able to make it happen this year and I said “you bet!” we’re going to make it happen!”  


We were very excited to work on this show for many reasons.  One, it is in our Regional “backyard”, being Singing Waiters in Chicago, but other is much closer to James’ heart….and heritage…a Greek-American himself, he was very excited to put together a fun and entertaining show with a special surprise twist to reflect Greek Heritage as well as the various musical tastes that this dynamic group of people would appreciate. “You guys knocked it out of the park!”, Dino exclaimed. “You hit every age group in the audience and they absolutely loved it. It was great!”

The Amazing Waiters in Chicago, IL

Hard to take photos of the actual show when you’re the surprise entertainment


It especially wonderful watching the younger audience members intrigued interested in what the show was delivering. Singing everything from Broadway, Opera, to Rat Pack-inspired music, made famous by The famed Las Vegas Trio in the 1950’s and 60’s, the diverse show was incredibly successful. To top it all off, James  surprised and entertained the guests by speaking Greek and seamlessly finishing with the Greek classic from Zorba the Greek, “Never On Sunday”, with James and Cassandra, (our latest addition who is also Greek) a Chicago native, singing and clapping along with the guests.  Even our third waiter, Chris who is not Greek had great fun dancing the Greek folk Style. 🙂


With one, two, and three waiters entertainment, our regional branch of The Amazing Waiters, Chicago Singing Waiters offer the most diverse and dynamic customized singing waiters shows in the United States. Find out how you can get the best Chicago Surprise Entertainment available, by calling 312-473-2919




Opera Singing Waiters Event Entertainment in Chicago

Opera Singing Waiters Event Entertainment just got more accessible in Chicago!

Entree Entertainment and The Amazing Waiters are happy to announce the availability of Opera Singing Waiters Event Entertainment in Chicago, Illinois.  Recently opening our latest regional branch in the Windy City, we are looking forward to working locally with many fabulous performers and clients to make the Chicago Live Entertainment scene just that much better.

Singing Waiters Midwestern Region Coverage

Our Chicago-based Singing Waiters will cover “local” areas across the Midwest, including Milwaukee, Bloomington, South Bend, Indianapolis, Detroit, Columbus and Toledo and all regions in between.

Amazing Singing Waiters Shows

For ideas on how The Amazing Waiters can be a great addition to your Wedding Reception, Business Meeting, Holiday or Small Party, see TAW website, or call toll free 855-899-7701 we are happy to discuss your event  with you!


With offices in southern california, las vegas, new york and now chicago.  See why the Amazing Waiters are the premiere surprise entertainment act in the united states.