City on Your Terms: A Private Scavenger Hunt Through Chicago’s Stories and Streets
An app-led urban game that turns Chicago’s landmarks into a living puzzle
You start at the edge of the river where the city seems to be holding its breath. Steel bridges lift like eyebrows and the water below glints with reflections of glass and brick. The app chimes, a gentle dare; the first riddle unfurls on your phone and then the city answers back. A painted bench, a bronze dog, a plaque that remembers a name from a century ago. The scavenger hunt turns downtown Chicago into a gameboard and the ordinary into a small, repeatable wonder.
Trail Wisdom
Charge Your Device
This tour is app-driven; bring a fully charged phone and a small power bank to avoid interruptions.
Wear Comfortable Shoes
Expect 1.5–2.5 miles of walking on city pavement with occasional stairs—supportive shoes matter more than fashion.
Plan for Weather
Lake-effect wind can change conditions quickly; pack a light windbreaker or layer up during spring and fall.
Start Near Transit
Begin at Millennium Park or the Riverwalk to minimize walking to the starting point and maximize sightseeing time.
Local Knowledge
Hidden Gems
- •A silent memorial bench tucked near a river bridge
- •An old greenhouse tucked behind a civic building that most tourists miss
Wildlife
Peregrine falcon, Canada goose
Conservation Note
Stick to sidewalks and public paths, use public transit to reduce car use, and pack out trash from any snack stops to protect river and park habitats.
Chicago’s post-1871 rebuilding fostered early skyscraper innovations; the Home Insurance Building, completed in 1885, is often cited as the first skyscraper.
Seasonal Guide
spring
Best for: Blossoming public gardens, Fewer tourists than summer
Challenges: Unpredictable lake winds, Occasional rain showers
Spring brings mild temps and flowering trees, but pack a windproof layer and expect occasional showers.
summer
Best for: Longer daylight, Lively street life and festivals
Challenges: Hot temperatures and crowds, Higher service demand at eateries
Summer is energetic with long evenings and busy plazas; hydrate and schedule early starts to avoid peak heat.
fall
Best for: Crisp air and changing light, Fewer tourists and great photo conditions
Challenges: Cooler evenings, Earlier sunsets
Fall offers ideal walking weather and vivid light for photography—bring a warm midlayer for late-day breezes.
winter
Best for: Quiet streets and holiday lighting, Shorter, focused walks
Challenges: Cold, icy sidewalks, Possible closures for severe weather
Winter scavenger hunts are atmospheric but require sturdy footwear and flexible scheduling around weather.
Photographer's Notes
What to Bring
Comfortable Walking ShoesEssential
Support for city sidewalks and short staircases makes the experience more enjoyable.
Portable Phone ChargerEssential
Keeps your device powered for the app and photos throughout the 90-minute tour.
Light Windbreaker or Layer
Useful for spring and fall when lake winds can cool you quickly.
Refillable Water BottleEssential
Staying hydrated is key, especially during summer’s heat and festival crowds.
Common Questions
How long is the scavenger hunt?
The experience runs about 90 minutes and usually covers 1.5–2.5 miles depending on the chosen route.
Is this suitable for kids or older adults?
Yes. The route is mostly flat and the puzzles can be adjusted for difficulty, though moderate mobility is helpful.
Do we need to print anything or meet a guide?
No printed materials are required. The tour is app-led and private, so there’s no guide to meet on-site.
Can we customize the route or start time?
Because this is a private experience you can choose a start location and time that work for your group within available booking windows.
What happens if the weather is bad?
You can reschedule or cancel per the operator’s policies. For light rain, the game can usually continue with umbrellas or rain jackets.
Are restrooms and food stops available along the route?
Yes. The Loop and Riverwalk have public restrooms and numerous cafes and vendors ideal for quick breaks.
What to Pack
Comfortable walking shoes for pavement; Portable phone charger to power the app; Refillable water bottle to stay hydrated; Light windbreaker for lake-effect winds
Did You Know
The Home Insurance Building in Chicago, completed in 1885, is widely regarded as the world’s first skyscraper due to its steel-frame construction.
Quick Travel Tips
Start near Millennium Park to minimize transit; Bring a charged phone and power bank; Wear weather-appropriate layers because the lake affects conditions; Carry small cash for food carts and quick purchases
Local Flavor
After the hunt, grab a deep-dish slice or a Chicago-style hot dog, stop by a nearby craft brewery for a pint, or visit the Chicago Cultural Center for free art and architecture exhibits to extend the urban discovery.
Logistics Snapshot
Closest airports: O'Hare (ORD) and Midway (MDW); Suggested start: Millennium Park or Riverwalk; Driving distance: most Downtown hotels are within 10–20 minutes; Cell service: generally excellent; Permits: none required for the private app-led tour
Sustainability Note
Use public transit to reach the start, avoid single-use plastics by bringing a refillable bottle, and respect public art and green spaces by not climbing or disturbing installations.