Turn Chicago’s streets into a holiday playground with Holly Jolly Hunt—an app-led scavenger hunt that sends teams hunting for festive sights, photo challenges, and local quirks across the Loop. Perfect for families, co-workers, or a spirited outing with friends.
More ways to explore the area's outdoor wonders
A crisp winter wind threads between glass and stone as a group taps their phones and disperses into the Loop — the city becomes both playground and puzzle. Holly Jolly Hunt turns sidewalks, storefront displays, and public art into checkpoints; teams follow photo prompts, complete lighthearted challenges, and race a live leaderboard visible in the app.
Difficulty
easy
Duration
1 hour
Fitness Level
Suitable for all fitness levels; requires light walking and standing for short periods
Wildlife
History
The Loop’s rebuilt streets and civic plazas reflect post–1871 fire reconstruction and a layering of architectural styles; holiday markets like the Daley Plaza Christkindlmarket draw on German-American traditions.
Conservation
Keep the game low-impact by photographing from public areas, disposing of trash in city bins, and supporting local small businesses you encounter rather than altering displays.
Reserve your spot on the Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Charge your phone
This app-based hunt depends on a charged smartphone—bring a portable battery to avoid interruptions mid-game.
Choose off-peak times
Late mornings or weekday afternoons reduce crowds and make photo challenges easier to complete.
Dress in layers
Chicago weather can swing quickly—wear insulated outerwear and removable layers for comfort between moving and standing.
Respect private property
Take photos from public sidewalks and approved vantage points; avoid entering restricted spaces for clues.
Smartphone with the Holly Jolly Hunt app
Required to receive clues, submit photos, and view the leaderboard.
Portable phone charger
Keeps your device powered through photo-heavy play and app usage.
Comfortable walking shoes
City pavements and quick sprints between clues make supportive footwear important.
Weather-appropriate outer layer
Windproof coat or hat and gloves in winter; a light rain jacket in wet seasons.
winter