Turn Chicago’s riverfront and plazas into a live gameboard: use an app, solve riddles, and photograph city objects while a remote host scores your antics. Perfect for groups who want a playful, social two-hour urban adventure.
More ways to explore the area's outdoor wonders
You step out onto a broad plaza with the river at your back and a stack of skyscrapers angling skyward; the game pings, the list loads, and downtown Chicago becomes a playground of riddles and photos. The Wacky Walks scavenger hunt routes wind through Heald Square and the nearby Vietnam Veterans Memorial, sending teams into alleys, riverfront promenades, and beneath the ironwork of bridges to find objects, perform dares, and score points.
Difficulty
easy
Duration
2 hours
Fitness Level
Light walking fitness; suitable for people who can walk steadily for 90–120 minutes with short stops.
Wildlife
History
Heald Square Monument honors Revolutionary War financiers and officers, while the nearby Vietnam Veterans Memorial commemorates local service members—both anchor the downtown route in layers of civic memory.
Conservation
Stick to marked paths, dispose of waste in bins, and avoid disturbing riverbank vegetation; Chicago River restoration efforts make the waterfront cleaner but still sensitive to litter and trampling.
Reserve your spot on the Scavenger Hunt in Chicago by Wacky Walks today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Charge your phone
The game runs through an app and requires photo uploads—start with a full battery and bring a power bank.
Comfortable footwear
Expect about two hours of walking on paved city surfaces—supportive shoes reduce fatigue.
Download transit passes
Public transit drops you close to the start—purchase or reload your card ahead of time to save minutes.
Off-peak timing
Avoid weekday rush hours for smoother gameplay and better photo ops along the riverwalk.
Smartphone with camera
Required to run the app, receive riddles, and upload photos for scoring.
Portable charger
Keeps your device powered through photo uploads and messaging with a remote host.
Comfortable walking shoes
Paved sidewalks and riverwalk surfaces demand supportive footwear for two hours of movement.
Refillable water bottle
Staying hydrated keeps energy up—water fountains and refill stations can be sparse along the route.
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