Race through the Loop with an app in hand and a remote host on speed dial. Operation City Quest turns Chicago’s streets into a two-hour scavenger hunt of photo tasks, local trivia and playful challenges.
More ways to explore the area's outdoor wonders
A brisk wind off Lake Michigan lifts the page of the city map as a group opens the Operation City Quest app and steps into the Loop. Streetlamps throw long shadows on the pavement, the river hums beneath bridges that fold the city into easy-to-navigate sections, and the scoreboard pulses on-screen — every photo, solved riddle and silly challenge nudges teams up the leaderboard.
Difficulty
easy
Duration
2 hours
Fitness Level
Casual walkers; suitable for families and most fitness levels — expect 1.5–3 miles of walking on flat, paved surfaces
Wildlife
History
Chicago’s Loop grew from a 19th-century grid and was reshaped after the Great Chicago Fire; its river and lakefront are products of large-scale 19th- and 20th-century engineering projects.
Conservation
Stick to sidewalks, dispose of trash properly and support local businesses encountered on the route; the Chicago River has seen major restoration efforts, so avoid disturbing wildlife near water.
Reserve your spot on the Chicago Scavenger Hunt by Operation City Quest today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Charge and protect your phone
The app and photo uploads are central — bring a full charge and a protective case or armband for comfortable use while walking.
Plan a flexible route
Choose an order of checkpoints that minimizes backtracking — the app lets you play in any sequence, saving time and energy.
Mind city etiquette
Be polite when shooting photos near shops or residents and avoid blocking sidewalks during busy hours.
Use public transit to reposition
Start or finish near an ‘L’ stop or Metra station to add checkpoints without extra walking time.
Smartphone with camera
Required for the app, photo tasks and chat with the remote host.
Portable battery pack
Keeps your phone charged through photo uploads and navigation for the full two hours.
Comfortable walking shoes
Support for pavement walking and occasional stairs along riverwalks and plazas.
Reusable water bottle
Staying hydrated is key in summer heat and during long photo hunts.
summer