THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
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.
Verified experiences and guided adventures in the surrounding area.
Operated by Holly Jolly Hunt - Holiday Scavenger Hunt · Chicago, Illinois
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.
Chicago’s streets carry layers of history: brick from post–Great Chicago Fire rebuilding, Beaux-Arts facades, and postwar modern towers. Holiday markets and seasonal lights lean on that architectural canvas, while Millennium Park and Daley Plaza provide obvious staging areas for festive clues. The game borrows the city’s culture — from office-window displays on Michigan Avenue to small storefront traditions in neighborhoods like Old Town.
Expect 45–90 minutes of walking at an easy pace, frequent stops for photos, and quick bursts of lateral thinking rather than strenuous exertion. The app includes remote guide chat support, and the experience is private for your group. It’s accessible by public transit and stroller-friendly, so mixed-age teams do well.
Plan for phone battery life and midday windows for best light on photos. If you want fewer crowds, schedule outside peak holiday hours; evenings offer atmosphere but can be colder and busier. Treat the hunt as a way to see familiar streets differently rather than to tick off every major sight—local cafés, public art, and a surprising alley mural often win the most points and the best memories.
easy.
1 hour.
Suitable for all fitness levels; requires light walking and standing for short periods
The standard session is about one hour, though groups can take 45–90 minutes depending on pace and how many challenges they attempt.
Yes. The hunt is stroller-accessible and designed for all physical fitness levels; most routes stay on public sidewalks and plazas.
No; clues guide you and the app includes a remote chat guide for help if you get stuck.
Full refunds are available if you cancel at least 24 hours before the scheduled start time; cancellations within 24 hours are nonrefundable.
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.
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.
Holly Jolly Hunt - Holiday Scavenger Hunt operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
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.
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.
Chicago’s streets carry layers of history: brick from post–Great Chicago Fire rebuilding, Beaux-Arts facades, and postwar modern towers. Holiday markets and seasonal lights lean on that architectural canvas, while Millennium Park and Daley Plaza provide obvious staging areas for festive clues. The game borrows the city’s culture — from office-window displays on Michigan Avenue to small storefront traditions in neighborhoods like Old Town.
Expect 45–90 minutes of walking at an easy pace, frequent stops for photos, and quick bursts of lateral thinking rather than strenuous exertion. The app includes remote guide chat support, and the experience is private for your group. It’s accessible by public transit and stroller-friendly, so mixed-age teams do well.
Plan for phone battery life and midday windows for best light on photos. If you want fewer crowds, schedule outside peak holiday hours; evenings offer atmosphere but can be colder and busier. Treat the hunt as a way to see familiar streets differently rather than to tick off every major sight—local cafés, public art, and a surprising alley mural often win the most points and the best memories.