Set off on a thrilling 5-day motorcoach journey to the heart of the Midwest — Chicago — where world-class sightseeing meets an unforgettable interactive mystery experience! Your adventure includes a relaxing four-night stay in the Chicago area, but this isn’t just a getaway… it’s a case waiting to be solved.
From the moment you board, clues begin to unfold.
Your itinerary is packed with the city’s best: enjoy a comprehensive Guided Tour of Chicago while uncovering suspicious details hidden in plain sight. Experience the fun and vibrant atmosphere of historic Navy Pier — but keep your eyes open… not everyone in your group may be who they claim to be. Relax on a beautiful Skyline Cruise across Lake Michigan, taking in spectacular views of Chicago’s iconic architecture — and perhaps gathering vital clues as the plot thickens.
Get a bird’s-eye perspective from 1,000 feet up at 360 CHICAGO on the famed Magnificent Mile, where you’ll also enjoy free time for shopping at Water Tower Place Mall. But even during free time, the mystery continues — secret alliances may be forming.
Delve into discovery at two world-class institutions: the Field Museum of Natural History (home to “Sue,” the T-Rex) and the acclaimed Museum of Science and Industry. Somewhere between ancient fossils and cutting-edge innovation, an important item disappears… and the suspects are among us.
Round out your fun with an evening of gaming at a Chicago-area casino — where luck, strategy, and deception all come into play.
Throughout the trip, guests will enjoy a fully immersive, lighthearted mystery woven into the journey. Meet colorful characters, uncover motives, collect clues, and work together to solve the case before the final reveal. Whether you’re a master detective or just along for the ride, this experience adds a whole new layer of excitement to an already unforgettable adventure.
With included dinners, iconic sightseeing, interactive fun, and non-stop surprises, this is not just the ultimate Chicago experience — it’s a mystery waiting to be solved.
Departure Date: Monday, June 22, 2026 from Walmart, 730 US-66 E, Tell City, IN
Price: $769* per person, double occupancy
Final Payment Due: April 15, 2026.
Travel insurance information for Diamond Tours can be purchased through Travel Confident.
Please check their website for pricing and other information. Insurance can only be purchased through the website.
Your deposit holds your seat on any of our trips. Please send your deposit as soon as possible.
To pay with check, make it payable to Diamond Tours and mail them to
215 N 4th St, Cannelton, IN 47520