Solve riddles and follow directions on your phone as you walk the Loop and River North, tracing Chicago’s rebirth after the Great Fire and the undercurrent of Prohibition-era gangsters. This 60–90 minute self-guided game mixes architecture, local lore, and urban navigation.
More ways to explore the area's outdoor wonders
You open the Questo app and the street unfurls: the river glints like a seam through the city and the double-deck of Wacker Drive hums beneath your feet. The game nudges you north across the Chicago River, past hotels and Gothic stone, and into a narrative that stitches together the ashes of 1871 with the city’s lawless Prohibition nights.
Difficulty
easy
Duration
60–90 minutes
Fitness Level
Light walking ability; suitable for most fitness levels and families with strollers.
Wildlife
History
The walk traces post-1871 reconstruction and the Prohibition era when Chicago’s rail and port connections fueled organized crime as well as legitimate commerce.
Conservation
River restoration and improved stormwater management have cleaned stretches of the Chicago River—stay on designated paths and avoid feeding wildlife to limit human impact.
Reserve your spot on the Chicago Gangsters: Self-Guided Crime Story Puzzle Walk today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Charge your phone and enable data
The game runs in the Questo app and uses maps and media; a full charge and data access prevent interruptions.
Wear comfortable, weatherproof shoes
Expect 1–2 miles of mostly flat pavement with frequent stops; slip-resistant shoes handle wet riverwalk sections.
Be mindful of traffic and crosswalks
You’ll cross busy streets and bridges—wait for signals and watch for bikes on the Riverwalk.
Start in daylight for best visibility
Clues and historical details are easier to read during the day; if you go in evening, stay on well-lit routes.
Smartphone with Questo app
Runs the game, displays clues and directions, and stores progress.
Comfortable walking shoes
Support for paved city sidewalks and short stair or curb transitions.
Portable battery pack
Keeps your phone powered through media, maps, and photos during the walk.
Light weather layer (shell or jacket)
Chicago winds and sudden showers are common—an outer layer helps between stops.
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