Discover 53 professional Dixieland bands available in Chicago, Illinois, United States for weddings, parties and special events. These traditional jazz ensembles bring authentic New Orleans style music with classic brass sections and vintage charm, backed by 123 reviews from real clients averaging 5 out of 5 stars.
All 53 suppliers listed here are willing to travel to Chicago. The nearest is based in Saint Charles, 34 miles away.
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Rates for Dixieland ensembles in Chicago typically run from about $160 to $1,700+, with an average booking fee of $850. Pricing reflects line-up size, performance duration and the group's experience. Many acts offer flexible configurations from intimate quartets to traditional seven-piece arrangements, allowing you to match both musical preferences and budget requirements. Contact the supplier you like for an accurate quote.
Based on 141 enquiries for Dixieland Bands at events in the United States, made through this site in the last two years. Updated 19 October 2026.
Big City Dixieland Band
"Big City Dixieland was a HUGE hit in our City Parade! Audiences from all ages were singing along, clapping and even dancing in the grass! Big City Dixieland sounded great! From what we (the organizers) could hear, they played a good variety of lively, well-known Dixieland Music, including a patriotic song. It was very easy to work with Maureen and Michael, their band arrived early, and everyone was very professional. We will definitely be hiring Big City Dixieland band for our next event in 2025!"
The Sidewalk Crusaders
"Great energy!!
We are so happy we booked The Sidewalk Cruisaders for our wedding. They brought so much energy and fun to our cocktail hour. My guests raved about them. Very easy to work with and willing to tailor the song list to our likes and interests."
Russell Wilson
"Russell was a wonderful addition to our party, not only his wonderful music, but also his fun personality."
Jazz Vocalist & Clarinetist Rick Bogart
"“ONE OF THE GREAT CLARINETISTS OF OUR ERA” - Danny Stiles WNYC Radio"
Texas Gypsies
"In a word... FABULOUS! These guys gave us just the sound we needed for our fun Prohibition-theme wedding. It is now two weeks later, and all we keep hearing is "Man, that band was fantastic!" They are worth the asking price (which is very reasonable to begin with!) Steve Curry is a great guy and very easy to deal with. I would recommend them without any reservations."
Efrayim Fischbacher
"I'm a professional I respect the music. I've never signed anything like this before."
