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.
More ways to explore the area's outdoor wonders
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.
Difficulty
moderate
Duration
1.5–2 hours
Fitness Level
Light to moderate fitness — able to walk 1–2 miles and stand for short periods
Wildlife
History
The route echoes Chicago’s cocktail culture born from Prohibition-era speakeasies and the city’s rapid post‑fire rebuilding that reshaped downtown circulation.
Conservation
Support local businesses by limiting litter and using public trash; urban tours should respect private property and keep noise down in residential areas.
Reserve your spot on the Astounding Chicago Bar Crawl: Chi-Town Showdown today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring a charged smartphone
The experience is app-led; keep battery and mobile data available for maps and photo uploads.
Carry a valid ID
Most stops include alcohol options — a government ID is required for anyone drinking.
Plan for flat urban walking
Expect 1–2 miles on paved sidewalks; comfortable shoes will make the route more enjoyable.
Hydrate between drinks
Alternate alcoholic beverages with water to stay alert while navigating busy streets.
Smartphone with data
Required to run the Let’s Roam app, receive clues, and upload photos.
Comfortable walking shoes
Paved city streets and standing at bars are easier with supportive footwear.
Portable charger
Preserves battery through map use, photos, and messaging during the hunt.
Light rain jacket or shell
Quick showers are common; a compact jacket keeps you moving between stops.
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