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The 3 Best 1920s Era Entertainers for Hire in Milwaukee, WI

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87 1920s Era Entertainers serving Milwaukee, WI
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1. Browse 1920s Era Entertainers in Milwaukee and contact your favorites

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2. Communicate with the 1920s Era Entertainment you select to work out the details of your event

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3. Book them through GigSalad and be covered by our 100% awesome guarantee!

1920s Era Entertainment Pricing

Pricing

Using data from quotes sent through GigSalad, we’ve gathered average pricing for hiring 1920s Era Entertainment in your region.

Our Worry-Free Guarantee

Worry-Free Guarantee

Booking a Milwaukee 1920s Era Entertainer through GigSalad offers you extra protection you can’t get anywhere else. You can rest easy knowing that your payment is secure, and that we’ll have your back in the event of any trouble that may occur. Learn more

What Milwaukee Users Say

5-star review

“Provided a perfect experience” – Phillip I., reviewing Chicago 1920s Era Entertainer The Gatsby Gang Jazz Band. More reviews

The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin Featured vendor banner
The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin

The Gatsby Gang Jazz Band

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5.0 (5)
  • Map pin icon Milwaukee, WI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Check mark icon 9 Verified Bookings

Debbie said “WOW - just WOW! We had a social event at our office and wanted to have some light jazz playing in the background. The group that came was just GREAT!…”

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Background Jazz Band - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin Featured vendor banner
Background Jazz Band - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin

Background Jazz Band

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4.91 (12)
  • Map pin icon Milwaukee, WI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Check mark icon 23 Verified Bookings

Amy C. said “Great music. Musicians that’s showed for my wedding were kind and professional. The first dance went smoothly. No concerns!”

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Crook & Company - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin Featured vendor banner
Crook & Company - Jazz Band / 1920s Era Entertainment in Milwaukee, Wisconsin

Crook & Company

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5.0 (4)
  • Map pin icon Milwaukee, WI
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Check mark icon 3 Verified Bookings

David V. said “We hired Crook and Company for our garden wedding reception outside Green Bay. They traveled 2 hours to get to us. They played as a duet for the cocktail…”

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Quick facts
1920s Era Entertainment in Milwaukee, WI

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1,152 quotes sent

In the past year, 1920s Era Entertainers have sent 1,152 quotes to event planners

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123rd most popular

1920s Era Entertainers rank #123 in popularity out of 542 categories on GigSalad

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5 out of 5 stars

679 1920s Era Entertainer reviews on GigSalad with an average rating of 5 stars

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1.2 days on average to book

From request to booking, it takes 1.2 days (on average) to hire 1920s Era Entertainer

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1920s Era Entertainment in Milwaukee, WI


If you’re planning a wedding, corporate event, or birthday party with a Roaring Twenties or Great Gatsby theme, you’ll need authentic 1920s era entertainment to pull it off. Get your guests doing the Charleston with live music from a jazz band or jazz singer. Or, hire flapper dancers to show them how it’s done. You can also keep the audience in their seats with a captivating vaudeville act or magic show.

The cost of booking 1920s entertainment in Milwaukee, WI will vary depending on the performance length, the type of performer you want, and the complexity of the show. A full show with a 1920s theme complete with multiple jazz musicians and flapper dancers in costume will charge more than a solo performer with a simpler setup. Contact the local 1920s entertainers above to get a quote customized for your event.

While browsing Milwaukee 1920s era entertainment, look through profiles to see photos and watch videos of their performances. Then read reviews from past clients to see if they have experience with events like yours and what it will be like to work with them. When talking with performers, discuss important details like setup requirements, event schedule, and any special requests for costumes, props, or songs.

Once you find the band or performer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to hire 1920s entertainment. You can talk with performers, confirm the details of 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! Search for 1920s Era Entertainment in Milwaukee, Wisconsin above.

Please note that these 1920s Era Entertainment may also travel to Shorewood, Saint Francis, Whitefish Bay, Glendale, Greendale, Fox Point, Elm Grove, Brown Deer, River Hills, Butler, Bayside, Hales Corners, Thiensville, Lannon, Pewaukee, Caledonia, Sussex, Raymond, Cedarburg, Colgate, Big Bend, Lisbon, Franksville, Wind Lake, Grafton, Richfield, Hubertus, Tichigan, Jackson, and Waterford.

Find 1920s Era Entertainment in nearby cities

Wauwatosa West Allis Cudahy Greenfield South Milwaukee Brookfield
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