12 Out-of-the-Box Chicago Wedding Entertainment Ideas

red carpet entertainer with guests at masquerade themed charity galaIf “extraordinary” and “unique” are the words you want to hear about your wedding entertainment, these ideas for themed wedding entertainers are for you. You know what we’re talking about: creative entertainers that amaze, unusual entertainment that fit with a one-of-the-kind wedding theme, or an entertaining act that makes guests feel like the ultimate night out in the Windy City.

Steel Drums

Transport your guests to the beach with tropical wedding entertainment. Think of it as a destination wedding at home. Your guests’ll love the signature tropical drinks, delicious tropical dishes, and sounds of a Caribbean island (especially on a cold Chicago day!).

aerialist at event hanging from ceiling

Aerialists

Take your wedding to new heights with aerialists—either for entertainment or for one of the most unique drink servers your guests have ever seen. Aerialists can be an extraordinary addition to an formal wedding or a whimsical touch to an upscale carnival themed wedding.

Performance Art

“Unexpected” is just one of the words your guests’ll be using as they are entertained by a unique performance art act. Contact an entertainment agent to select the right act compatible with the desired wedding atmosphere.

Magician

Bring the magic of you are as a couple to life with this unusual wedding entertainment. Contact an experienced pro who can select the right magician that can customize their act. To up the ante, ask your entertainment agent to coordinate the act into a surprising part of the wedding reception program.

Carnival Performers

Make your wedding more than just another event. Bring on the show! Plan a spectacular wedding with a fabulous dance troupe and a glamorous flare.

wedding entertainers

Artists

Art is a fantastic wedding entertainment that can entertain wedding guests of all ages. Face painters are a terrific way to entertain children (and some adults too). Caricature artists give guests an unexpected memory from a fun evening. A wedding painter can capture the wonder of a wedding and provide a wonderful painting for the future.

Tropical Bands

Heat up your wedding reception with a mariachi or reggae band. Your guests’ll appreciate the exceptional sounds, and bask in the feel of a tropical wedding atmosphere.

mardi gras entertainer with pink and purple dress and drink servers on the skirt

Champagne Girl

Champagne girls are an awesome and unexpected detail that has a BIG impact on guests. Guests’ll enjoy the entertaining aspect and uniqueness of the service. (Hopefully they’ll also enjoy the drink served, if you choose carefully!)

Jazz Band

Nothing completes a vintage wedding or jazz lounge atmosphere like jazz entertainment. And like this one-of-a-kind entertainment choice, a professional entertainment pro can help you choose the right act for your big day.

Celebrities

A celebrity can be just the entertainer than can spice up a wedding reception, but we don’t all have the budget to fly in our fave. However, your wedding reception can still feel like a Hollywood ball with visits by top look a-likes that can make everyone feel like they are in the presence of greatness.

great gatsby entertainers

Period Entertainers

Nothing takes a guest back to the period of a vintage wedding like a group of entertainers dressed in the styles of the 1920’s, 1930’s, 1950’s—really any period. Period entertainers can mingle, perform acts, or do anything that makes a wedding feel authentic. To connect with the right entertainers, contact an entertainment agent that is familiar with local acts that can put a wedding reception over-the-top.

Holiday Show

A Halloween Mystery or a Holiday Caroling Show is not what any guest expects to see at a wedding—and is what makes this out-of-the-box wedding entertainment so spectacular. These seasonal entertainers are a great match for a holiday themed wedding where a couple wants a one-of-a-kind main stage entertainment.

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