THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
An app-led bar crawl that doubles as a scavenger hunt across downtown Chicago. Expect 1.5–2 hours of photo challenges, neighborhood trivia, and short bar stops with flat, walkable routes.
An app-led bar crawl that doubles as a scavenger hunt across downtown Chicago. Expect 1.5–2 hours of photo challenges, neighborhood trivia, and short bar stops with flat, walkable routes.
A late afternoon wind from Lake Michigan pushes through a block of brick and glass as your group unlocks the Let’s Roam app and spills onto the sidewalk. The game maps a 1–2 mile loop through downtown and neighborhood streets, alternating quick puzzle stops, photo challenges, and short bar breaks that reward creativity as much as speed.
Verified experiences and guided adventures in the surrounding area.
Operated by Let's Roam · Chicago, Illinois
A late afternoon wind from Lake Michigan pushes through a block of brick and glass as your group unlocks the Let’s Roam app and spills onto the sidewalk. The game maps a 1–2 mile loop through downtown and neighborhood streets, alternating quick puzzle stops, photo challenges, and short bar breaks that reward creativity as much as speed.
Chicago’s streets carry layers of history — from the 19th‑century rebuilding after the Great Fire to the Prohibition-era speakeasy routes that shaped the modern bar scene. Geology is subtle here: the city sits on glacial sediments and the lake’s edge, so expect flat, paved terrain and long sightlines along the river and the lakefront. The culture is convivial and competitive: neighborhoods trade local beer recommendations like postcards, and public art and plaques become clues in the hunt.
Practically, this is a self-guided, app-led experience that runs about 90–120 minutes and is best started in late afternoon to hit bars as they open. Terrain is entirely urban — sidewalks, crosswalks, occasional steps — with negligible elevation gain. Bring a charged smartphone, a valid ID, and comfortable shoes; the app times and tracks challenges, but you control pace and stops.
Expect photo tasks, trivia tied to plaques and statues, and quick social activities that reward teams for clever answers. Be mindful of peak evening crowds on weekends, keep valuables secure, and plan a transit route home. This blend of city history, pub culture, and navigation makes for a playful way to explore Chicago with friends while testing your local savvy.
moderate.
1.5–2 hours.
Light to moderate fitness — able to walk 1–2 miles and stand for short periods
No — this is self-guided. Once you redeem your voucher in the Let’s Roam app you can start when you’re ready during operating hours.
The typical hunt lasts 1.5–2 hours and covers about 1–2 miles; the number of bars depends on the route and how many stops your team chooses.
Yes — the provider notes wheelchair accessibility, but check individual bars for ADA details such as step-free entry and restroom access.
The experience is flexible — non-drinkers can participate fully in clues and photo challenges and enjoy non-alcoholic options at stops.
The route echoes Chicago’s cocktail culture born from Prohibition-era speakeasies and the city’s rapid post‑fire rebuilding that reshaped downtown circulation.
Support local businesses by limiting litter and using public trash; urban tours should respect private property and keep noise down in residential areas.
Let's Roam operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
A late afternoon wind from Lake Michigan pushes through a block of brick and glass as your group unlocks the Let’s Roam app and spills onto the sidewalk. The game maps a 1–2 mile loop through downtown and neighborhood streets, alternating quick puzzle stops, photo challenges, and short bar breaks that reward creativity as much as speed.
A late afternoon wind from Lake Michigan pushes through a block of brick and glass as your group unlocks the Let’s Roam app and spills onto the sidewalk. The game maps a 1–2 mile loop through downtown and neighborhood streets, alternating quick puzzle stops, photo challenges, and short bar breaks that reward creativity as much as speed.
Chicago’s streets carry layers of history — from the 19th‑century rebuilding after the Great Fire to the Prohibition-era speakeasy routes that shaped the modern bar scene. Geology is subtle here: the city sits on glacial sediments and the lake’s edge, so expect flat, paved terrain and long sightlines along the river and the lakefront. The culture is convivial and competitive: neighborhoods trade local beer recommendations like postcards, and public art and plaques become clues in the hunt.
Practically, this is a self-guided, app-led experience that runs about 90–120 minutes and is best started in late afternoon to hit bars as they open. Terrain is entirely urban — sidewalks, crosswalks, occasional steps — with negligible elevation gain. Bring a charged smartphone, a valid ID, and comfortable shoes; the app times and tracks challenges, but you control pace and stops.
Expect photo tasks, trivia tied to plaques and statues, and quick social activities that reward teams for clever answers. Be mindful of peak evening crowds on weekends, keep valuables secure, and plan a transit route home. This blend of city history, pub culture, and navigation makes for a playful way to explore Chicago with friends while testing your local savvy.