đź“… Open Today: Crawl likely not fully open on Sundays
Explore Chicago Loop’s vibrant bar scene with our cocktail crawl! Start at RAISED, a stylish rooftop lounge with skyline views and craft cocktails. Then step into Brando's Speakeasy for vintage vibes, hidden in a historic building with karaoke and dancing. Next, enjoy tropical cocktails and house daiquiris at Three Dots and a Dash’s retro Polynesian setting. Finish at Miller's Pub, a cozy American pub serving up classic bites and brews. Perfect for a fun night out full of drinks, atmosphere, and good times!
Last updated: June 2025
Let's kick off your evening way up high with the stunning Chicago skyline, then dive right into the city's lively heartbeat on this fun cocktail bar crawl. Each stop brings a fresh burst of energy—starting at Raised’s dynamic rooftop lounge, where those sweeping river views and artisanal drinks get the party started. Next, slip into the sultry vibes of Brando’s Speakeasy, where karaoke and classic cocktails spark some playful connections. Then, whisk yourself away to the tropical escape of Three Dots and a Dash, a retro Polynesian spot with exotic rums and amazing tiki drinks. Finally, wind down at Miller’s Pub, a beloved Chicago gem offering hearty American eats and craft brews in a warm, welcoming space. This crawl is perfect for anyone craving an adventurous night out, filled with diverse scenes, great drinks, and that nonstop social buzz.
Kick off your night with those breathtaking skyline and river views at Raised’s rooftop lounge, where approachable craft cocktails and a buzzing atmosphere crank up the excitement high above the Loop.
The next spot is just a short, energizing walk into the heart of the Loop’s nightlife, shifting from that open-air glamour to a cozy, vintage speakeasy feel.
Dive into Brando’s atmospheric speakeasy, where classic cocktails meet karaoke-fueled fun, adding a playful, retro twist with music, dancing, and expertly mixed drinks that keep the energy high.
The next stop is a lively stroll that eases the vibe from jazz-age charm to tropical sophistication in a vibrant tiki setup.
Escape to a Polynesian-inspired oasis where exotic rums and house-made daiquiris whisk you away to an upbeat tiki paradise, pumping fresh energy into your night out.
The next spot is a welcoming walk back toward the Loop’s historic core, grounding the evening with classic pub vibes, hearty fare, and craft brews.
Wrap up your adventure at Miller’s Pub, a timeless Chicago favorite offering hearty American dishes and robust craft brews in a warm, convivial spot that keeps the good times rolling.
The crawl wraps up right here, blending comfort and celebration in the heart of the Loop for a perfect end to the night.
From those epic rooftop panoramas to hidden speakeasy beats, tropical getaways to classic Chicago hospitality, this cocktail bar crawl serves up an electrifying night in the Loop. Grab your crew, follow this easy route, and soak in the city’s best-crafted cocktails and lively vibes. Ready for your next epic nightlife escapade? Chicago’s Loop is calling—here’s to making memories!
Crawl Map