Chicago: Murder Mystery Walking Tour & True Crime Game

Summary

Chicago’s secrets unfold as you play detective solving a murder

You’ll dive into Chicago’s true crime legends as you play detective on foot, solve clues with your group, interrogate “suspects,” and wander historic neighborhoods from Water Tower Place to Gold Coast. Expect laughter, surprises, and real stories that stick with you long after your mugshot photo goes home with you.

What’s the experience like?

I’ll admit, I didn’t expect to start my Saturday standing outside Water Tower Place, nervously clutching my “detective badge” sticker. Our guide—who actually called himself Detective Mike—handed it out with a grin and asked if any of us had ever solved a crime before. (I hadn’t, unless you count losing my keys.) The city felt extra alive that morning: sirens somewhere distant, the smell of roasted peanuts from a vendor, and this weird sense that maybe we were about to uncover something real beneath all the skyscrapers.

We moved through Michigan Avenue, not just gawking at shops but listening to stories about Chicago’s wild Prohibition days. Detective Mike would pause—sometimes mid-sentence—to point out where some gangster supposedly ducked into an alley. At one point, he had us “interrogate” each other in front of the National Portrait Gallery. My friend tried her best tough-cop impression; it was honestly terrible but made everyone laugh (even Mike). The whole murder mystery game part was more fun than I thought—clues tucked into corners, little details you’d miss if you weren’t looking.

The best part for me? When we wandered through Gold Coast, past these old mansions with iron fences and perfect lawns. There was this moment on the lakefront trail where the wind picked up and I could smell the water mixed with something sweet—maybe someone’s cologne or bakery nearby? We were supposed to be eliminating suspects but I got distracted by the view for a second. Oh, and those souvenir mugshot photos at the end—I look ridiculous in mine but it still makes me smile when I see it on my fridge.

Step-by-step itinerary

Day 1 — Chicago murder mystery walking tour

• Meet lead detective at historic building
• Explore busy commercial district
• Interrogate suspects in wealthy neighborhood
• Eliminate suspects along lakefront trail

Top questions

How long is the Chicago Murder Mystery Tour?

The tour covers about 1.2 miles over 2 hours.

Is the tour wheelchair accessible?

Yes, all areas and surfaces are wheelchair accessible.

Are children allowed on this tour?

Yes, infants and small children can join in a stroller or pram.

Where does the tour start?

The experience begins outside Water Tower Place in Chicago.

Do I need to bring anything special?

No special equipment is needed; just dress for outdoor walking.

Are service animals allowed?

Yes, service animals are permitted on this tour.

Is public transportation nearby?

Yes, there are public transportation options close to the meeting point.

What’s included in the price?

You get guided walking tour activities plus souvenir mugshot photos.

What’s included

Your day includes an outdoor walking tour through Chicago’s historic streets led by a local guide playing “lead detective,” interactive murder mystery game elements along famous spots like Water Tower Place and Gold Coast, plus souvenir mugshot photos to take home as a reminder of your detective skills before heading off on your own adventures again.