An app-guided, walkable cocktail crawl through Chicago’s Loop: rooftops, speakeasies, and historic bars with views of the river and landmark architecture. Perfect for an independent, grown-up night out.
More ways to explore the area's outdoor wonders
The city unwraps itself in glass and stone as you step out on the Riverwalk and head toward LondonHouse’s rooftop — traffic hums below while the skyline angles toward you like a built horizon. This self-guided cocktail crawl threads six historic drinking rooms through the Loop, each stop a short walk from the last, with river views, vaulted library facades and the odd iron-and-brick monolith punctuating the route.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Light walking fitness; able to walk short distances on flat, urban sidewalks and stand inside venues
Wildlife
History
The Loop’s bar culture evolved through 19th-century saloons, Prohibition-era speakeasies and modern craft-cocktail revival, with many venues interpreting those eras in their menus and ambience.
Conservation
Choose public transit or walking to reduce impact, bring reusable bottles, and support independent bars that source local ingredients when possible.
Reserve your spot on the Chicago Cocktail Adventure Part 1 today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring government photo ID
You must be 21+ to drink — have your ID ready at each bar to avoid delays.
Pace yourself with water and snacks
Rotate cocktails with water and share small plates to keep your energy up during a three-hour crawl.
Wear comfortable shoes
Expect 1–2 miles total on paved sidewalks; supportive footwear reduces foot fatigue.
Keep your phone charged
The eATLAS app provides maps and prompts — bring a portable charger for uninterrupted navigation.
Government-issued photo ID
Required to purchase or sample alcoholic drinks; carry it at all times.
Comfortable walking shoes
Supportive shoes make the 1–2 miles of pavement between stops much more pleasant.
Portable phone charger
Keeps the eATLAS app and maps running through the full adventure.
Reusable water bottle
Staying hydrated helps you enjoy multiple cocktail stops, especially on hot days.
summer