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6 Creative Chicago Picnic Entertainment Ideas

Every year, we look forward to picnic season and the relaxing days, delicious lunches and fun-filled afternoons it brings. Picnics are fun all by themselves—after all, a mouthwatering cheeseburger and lively conversation provide a much-needed break from the work day—but we challenge you to elevate your corporate picnic to the next level.

Exotic Animal Show at Company Picnic
What is the most enjoyable way to enhance your event? The answer is simple: find creative entertainment. We work with amazing vendors and have many, many years of picnic experience, so we have gathered these six incredible Chicago picnic entertainment ideas and paired them with menu items and theme suggestions to inspire your next corporate picnic.

Innovative Entertainment Ideas to Elevate Your Chicago Picnic

Fortune Teller

Have you ever wondered what lies in your future? Whether you believe in the mystical or not, it is always fun to imagine a life of adventure, mystery or luxury. You and your guests will enjoy the sometimes serious, sometimes seriously funny predictions that a fortune teller makes.

Fortune Teller at Company Picnic

  • Possible theme: Myths & Magic
    Magic is captivating, so any event with a hint of the mythical will be absolutely entertaining. Style your picnic around ancient Greece or medieval wizardry and your guests will be enchanted.
  • Suggested menu item: A Very Mediterranean Picnic
    If you do decide to host a Grecian picnic, there is nothing more delicious and fitting to serve! Enjoy chicken souvlaki skewers, red pepper hummus and much more.

Stilt Walker

Children and adults alike will marvel at the colorful people towering over them. Stilt walkers add dimension to your picnic, fearlessly strolling among your guests and becoming an easy conversation starter.

  • Possible theme: Circus Celebration
    We cannot think of an event more entertaining than the circus. Daring acrobats and sweet treats make for a truly memorable day.
  • Suggested menu item: Rodeo Grill
    The circus is full of life and laughter, so the food should reflect that. Bursting with smoky, sweet and savory flavors, you will love the 18-hour smoked brisket, molasses baked beans and more.


Who wouldn’t want to have Elvis at their picnic? Impersonators are not just topics of conversation, they can have one with you! See which famous person your guests would like to meet most and make their day.

Impersonator for Company Picnic

  • Possible theme: Hollywood
    We all dream of fame and fortune, and you could make your guests’ dreams come true, even if just for a day. Let them live the glamorous life for a few hours and they are sure to make many memories.
  • Suggested menu item: Food Truck Fusion
    When it is lunch time on set, celebrities do not need to walk to the closest fast food place. Instead, they dine on delicious, creative food truck cuisine like Asian pulled pork sliders and street tacos.

Sand Artist

These innovative artists are becoming very popular—and for good reason. Their temporary and ever-changing art is the object of wonder and awe for many and is sure to produce the same reactions in your guests.

  • Possible theme: Tropical Paradise
    Smooth, warm sand reminds people of summer and the beach. Delight your guests with a mini-vacation by transforming your company picnic into a tropical paradise.
  • Suggested menu item: Caribbean Pig Roast
    The flavors of the Caribbean are oh so delicious and immediately make you want to relax on a beach. Enjoy the summer sun with Barbados-style barbecue, sliced golden pineapple and more.

Trackless Train

This one is more for the kids, but adults are welcome too! A trackless train gives rides around the entire celebration, delighting its passengers all day long. Your youngest guests are sure to enjoy their adventure while the adults socialize.

Trackless Train on Company Event

  • Possible theme: Around the World
    Typically, employees have to take a day off to travel. With this picnic theme, going into work becomes a vacation, with entertainment, cuisine and more from all across the globe.
  • Suggested menu item: Oktoberfest Pig Roast
    Not everyone can go to Germany for Oktoberfest, but you can bring a taste of the delicious festival to your guests with dishes like bratwurst and German potato salad.

Exotic Animal Show

From brightly-colored birds to wild jungle cats, mysterious reptiles and adorable miniature mammals, an exotic animal show entertains guests of all ages, allowing them to experience their own private zoo.

  • Possible theme: Into the Wild
    Nothing is more exciting than a safari. Though you probably cannot take your guests to the jungle, you can bring the thrill of adventure to them.
  • Suggested menu item: Baja Picnic
    A wild picnic theme deserves wild flavors, and the Baja Picnic is packed with delicious bites, including citrus barbecue chicken and mexicali rice.

Whatever entertainment, theme or menu you choose, we are always more than happy to help you create and coordinate the most successful, memorable company picnic. Call us today at 847-593-2000 or contact us to begin planning the perfect corporate picnic.

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