How to Book Corporate Entertainment in Chicago That Actually Delivers
How to Book Corporate Entertainment in Chicago That Actually Delivers
If you’re planning a corporate event in Chicago, you already know the pressure’s on. There are a million options in this city, venues with skyline views, rooftop patios, Michelin-starred catering… but the one thing that will stick in everyone’s mind? The entertainment.
As a corporate magician who performs all over the Midwest, I’ve learned that entertainment is the piece most often overlooked until it’s too late. But done right, it can completely change how people experience your event.
Why Entertainment Can Make or Break Your Event
Look, most corporate events follow the same template: name tags, awkward chit-chat, dry presentations, and a buffet. When you throw in unforgettable entertainment, you flip the script. Suddenly people are laughing, clapping, taking videos, and talking about your event long after it ends.
It’s not just about having fun (although that matters). It’s about connection. Team morale. Client impressions. Culture.
Exploring Entertainment Options for Corporate Events
Chicago’s full of talented performers, from jazz trios to keynote speakers. I’ve seen them all, and there’s value in each depending on your goals. But I’ve found that magic—especially the kind I do, which blends mentalism, sleight of hand, and comedy—hits that sweet spot between classy and crowd-pleasing.
It works because:
It’s interactive and personalized
It suits formal galas just as well as casual parties
It gets people genuinely engaged
It plays well to a wide range of ages and personalities
Magic in a corporate setting isn’t about pulling rabbits out of hats. It’s about creating moments of surprise that make people say, "how the hell did that happen?" And then laugh about it with the person next to them.
Choosing the Right Entertainer: What to Keep in Mind
Here’s what I’d recommend keeping an eye out for:
Corporate experience. You don’t want someone whose last gig was a birthday party.
Professional communication. This includes everything from first email to post-show follow-up.
Tone awareness. Can they be funny without being inappropriate?
Adaptability. Because things never go exactly to plan.
Tech-friendly. Mic-ready. Plug-and-play. No drama.
Questions You Should Ask (Yes, Even Me)
Have you worked events like ours before?
Do you require any special tech or setup?
Can you keep the material work-appropriate but still fun?
Can I see some reviews or video clips?
What happens if we run behind schedule?
If someone can’t answer those easily, they’re not the right fit.
What I Bring to the Table
I offer three main options for corporate clients:
Strolling Close-Up Magic – Ideal for receptions, cocktail hours, or during dinner. I move table to table or group to group, creating little magic moments that get people talking.
Comedy Magic Show – A high-energy, interactive stage show that’s built for business audiences. Think laughter, mind-reading, and a few "did that really just happen?" moments.
Full Experience – I combine both strolling magic and a formal show for events that need entertainment from start to finish.
Every show is tailored to the vibe of the event. Whether you're hosting clients at a high-end venue or throwing a holiday party for your internal team, I’ve got you covered.
Great Chicago Venues That Work Well With Entertainment
Here are a few local spots I’ve worked that pair beautifully with live entertainment:
Artifact Events – Modern-industrial feel with great AV support.
The Dalcy – Upscale and versatile, perfect for formal gatherings.
Morgan MFG – Big, flexible, and ideal for larger groups.
City Hall Events – High ceilings, stylish decor, and a great flow for strolling magic.
If you’re still figuring out logistics, I’m happy to make suggestions based on the size and format of your event.
Let’s Make Your Event a Hit
If you're planning a corporate event in Chicago and want it to stand out—not just on paper, but in people's actual memories—reach out. I’d love to help you pull off something unforgettable.
Let’s chat about your event and see if I’m a good fit.