- Chicago, IL
- Oldies Music
- $575-$2500
Paul D. said
“Jerry was an absolute professional and did an awesome job as an Elvis impersonator. Would definitely book him again. Thanks! ”
The 36 Best Oldies Music Groups for hire in Chicago, IL
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102 Oldies Music Groups serving Chicago, IL
The Saratogas
New member- Schaumburg, IL
- Oldies Music
- 26 miles from Chicago
- Contact for rates
Playing retro hits from the 60s thru the 80s: Motown, Soul, Yacht Rock & Classic Rock with some dance and party music to keep the party going! You'll love...
Gary Jacklin Band
1 Verified booking- Chicago, IL
- Oldies Music
- $500-1200
Gary, Andy and Pat first met in high school and have been performing virtually all of their lives. They've racked up hundreds of shows in musical acts across...
- Elmhurst, IL
- Oldies Music
- 16 miles from Chicago
- $175-$600
Kathryn B. said
“I hired Leslie for a gig in another state as a present. She was very organized and detailed in her communication, and I have every confidence she led a lovely holiday sing along. ”
- Des Plaines, IL
- Oldies Music
- 17 miles from Chicago
- $200 and up
Johnathan W. said
“I am very biased when it comes to musical entertainers and their abilities, especially when it is a work function and my reputation is on the line. They have to communicate extremely well in... ”
RetroActive
2 Verified bookings- Tinley Park, IL
- Oldies Music
- 23 miles from Chicago
- $300 and up
RetroActive is an exciting band playing the hits of the 60's, 70's, & 80's! There are 4 musicians in the group - all of whom sing. The result is great harmonies...
The Saddle Shoe Sisters
- Lyons, IL
- Oldies Music
- 11 miles from Chicago
- $425 and up!
Betsy K. said
“The audience at The Little Traveler was delighted by the performance of The Saddle Shoe Sisters. We were singing along and, by the end, people were dancing in the aisles. Liz Berg and her... ”
- Oak Lawn, IL
- Oldies Music
- 13 miles from Chicago
- $100-$150 per hour
Sing good old-time rock and roll and soul from the 50s thru 80s. I will turn your party or event into a sock hop. Your attendees can dance to my music as I sing...
Estimate the cost
We’ve gathered average pricing for hiring Oldies Music in Chicago, IL using data from quotes sent through GigSalad.
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Quick facts for Oldies Music in Chicago, IL
3,701 quotes sent
In the past year, Oldies Music have sent 3,701 quotes to event planners.
59th most popular
Oldies Music rank #59 in popularity out of 539 categories on GigSalad.
5 out of 5 stars
There are 1,982 Oldies Music reviews on GigSalad with an average rating of 5 stars.
1.6 days on average to book
From request to booking, it takes 1.6 days (on average) to hire a Oldies Music.
Chicago ranks #1
Chicago is the most popular city for Oldies Music requests in Illinois.
Popular events
Oldies Music are typically hired for Festivals, Wedding Receptions, and Birthday Parties in Chicago, IL.
Illinois ranks #3
Illinois is the 3rd most popular state for Oldies Music requests in the United States.
Past events for Oldies Music in Chicago, IL
Wonderful entertainment for Christmas Eve
Oldies Music
5.0
December 25, 2025
1 hour
Greg came to my Xmas Eve dinner. It was a last minute request. He was able to sing vintage frank sinatra and all the classic Christmas songs I grew up listening to with my father. My family loved the addition of live music. He read the room and interacted with everyone. He was great!
Event total
$153
About booking Oldies Music in Chicago, IL
Take a trip down memory lane with some live oldies music! Fill your next event with nostalgic hits from the 1950s, 60s, and 70s. Hire an oldies band or musician to play fun dance music at your wedding reception, prom, corporate event, anniversary, or decade-themed party. Check out the profiles above to find local oldies bands for your special event.
The cost of booking oldies music in Chicago, Illinois can vary depending on the length of the event, the size of the group, and their skill level. Large party bands with full costumes and years of experience may charge more for their performances but are well worth the price. Contact oldies music acts near you to get a quote customized for your event.
When browsing profiles for Chicago oldies music groups, look through photos, listen to audio samples, and watch videos to learn more about their services and style. Then read reviews from past clients to see what it would be like to work with them. When talking with professional oldies groups, discuss important details like arrival times, setup requirements, costume preferences, and any song requests you might have.
Once you find an oldies band or musician to hire, finalize the booking through GigSalad. Our full-service platform makes it easy to book live music for public events and private parties. You can message the performer, confirm the agreement, and make a secure payment all in one place. Every GigSalad booking is protected by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and enjoy the show!
Oldies Music serving the Chicago, IL area
These Oldies Music serve the wider Chicago and Cook county area and travel to Lincoln Park, Cicero, Irving Park, Oak Park, Berwyn, Stickney, Forest Park, Forest View, Elmwood Park, North Riverside, River Forest, Lincolnwood, Riverside, Amf Ohare, Lyons, Hines, Maywood, Harwood Heights, River Grove, Summit, Summit Argo, Burbank, Hometown, Evergreen Park, Broadview, Norridge, Melrose Park, Evanston, Brookfield, and Skokie.