Banner image for 1940s Era Entertainment
0%

Just a couple more things…

We need some additional information to ensure we find the perfect talent for your event!

91 1940s Era Entertainers serving Chicago, IL

The Irving Sisters

4.80 (1)
2 Verified bookings

  • Chicago, IL
  • 1940s Era Entertainment
  • $500 and up

Marta L. said “The Irving Sisters put on a great show that is entertaining to the young and old alike. Those of advancing years will be brought right back home to the songs of their youth. But these songs are... ”
Featured

John Behling Guitarist

5.0 (59)
Top Performer
93 Verified bookings

  • Chicago, IL
  • Guitarist / 1940s Era Entertainment
  • $300-$1500

Barbara G. said “John was prompt, personable and provided music appropriate for our fiesta themed event. Very positive response from our guests. Highly recommend him if you are looking for talented musician who... ”
Featured

Greg Rogalinski

4.93 (80)
Top Performer
150 Verified bookings

  • Chicago, IL
  • Frank Sinatra Impersonator / 1940s Era Entertainment
  • $100 ‐ $1,000

Bruce S. said “If you are looking to bring the magic, warmth, and effortless cool of Frank Sinatra to your event, look no further than Greg Rogalski. From start to finish, Greg was a absolute dream to work... ”
Featured

The Jazz Arts Duo

4.95 (18)
Top Performer
29 Verified bookings

  • Chicago, IL
  • Jazz Band / 1940s Era Entertainment
  • $500 - $2000

Sharon L. said “Will definitely hire again. They were great for the venue and vibe we were looking for. ”

Estimate the cost

We’ve gathered average nationwide pricing for hiring 1940s Era Entertainment using data from quotes sent through GigSalad.

See pricing

Book with confidence

When you hire a Chicago 1940s Era Entertainer through GigSalad, you’re backed by our Worry-Free Guarantee. From secure payments to reliable support, we’ve got your back.

Learn more

Quick facts for 1940s Era Entertainment in Chicago, IL

242 quotes sent

In the past year, 1940s Era Entertainment have sent 242 quotes to event planners.

263rd most popular

1940s Era Entertainment rank #263 in popularity out of 539 categories on GigSalad.

5 out of 5 stars

There are 816 1940s Era Entertainment reviews on GigSalad with an average rating of 5 stars.

Chicago ranks #1

Chicago is the most popular city for 1940s Era Entertainment requests in Illinois.

Popular events

1940s Era Entertainment are typically hired for Birthday Parties and Corporate Events in Chicago, IL.

Illinois ranks #3

Illinois is the 3rd most popular state for 1940s Era Entertainment requests in the United States.

About booking 1940s Era Entertainment in Chicago, IL

From swinging big band sounds and close-harmony vocal trios like the Andrews Sisters to the classic World War II era USO-style shows and vintage variety acts, 1940s era entertainment brings the elegance and spirit of a legendary decade to life. Whether you’re planning a nostalgic birthday bash, a vintage-themed fundraiser, or a formal corporate affair, a 1940s act can transport your guests back in time with smooth tunes, dapper style, and captivating stage presence.

The average cost to hire 40s entertainers in Chicago, IL will depend on several factors, including the type of performance, the number of entertainers, the distance they need to travel, and the length of the show. Share as many event details as possible when reaching out so performers can provide a personalized quote.

Before hiring Chicago 1940s entertainment, explore each act’s GigSalad profile. You’ll find videos, audio clips, and reviews from previous clients to help you get a feel for their performance style and how they’ve wowed audiences in the past.

Once you find the perfect performer, group, or band you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book talented entertainers. You can message the performers directly, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and enjoy the vintage vibes!

1940s Era Entertainment serving the Chicago, IL area

These 1940s Era Entertainment 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.