đź“… Open Today: Crawl likely not fully open on Sundays
Explore Chicago Loop’s vibrant bar scene with our cocktail crawl! Sip craft cocktails at RAISED, enjoy vintage vibes at Brando's Speakeasy, indulge in tropical classics at Three Dots and a Dash, and unwind at Miller's Pub. Whether you’re into rooftop views, hidden speakeasies, or classic American pubs, this crawl has it all—perfect for a fun night out with friends. Discover four iconic venues packed with great drinks, good times, and unforgettable memories!
Last updated: June 2025
Hey, let's dive into the heart of Chicago's Loop for a lively cocktail adventure that's packed with energy and style. Start your night with those stunning skyline views and cleverly crafted cocktails at a buzzing rooftop bar. Then, ease into the cozy charm of a vintage speakeasy, where karaoke and dancing bring the fun. Next up, whisk yourself away to a retro Polynesian paradise with tropical drinks and rums stealing the show. Wrap it up at a beloved Chicago spot, enjoying hearty eats and craft brews that keep the good times rolling. This whole adventure is a mix of social vibes and diverse spots – ideal for anyone wanting more than just drinks, but a night that'll stick with you.
Kick things off high above the city with awesome craft cocktails and those sweeping river and skyline views. This hip rooftop spot sets a fun, lively tone with its blend of indoor-outdoor energy and stylish decor – just the perfect spot to launch your adventure.
The next stop is a quick, refreshing walk through the bustling Loop streets, swapping open-air vibes for a cozy, hidden lounge.
Step into this vintage-inspired speakeasy that cranks up the excitement with its intimate vibe and lively karaoke stage. It's all about bespoke cocktails, spirited sing-alongs, and dancing in a historic setting that keeps the energy high.
The next stop is an easy walk that shifts from that sultry speakeasy feel to a vibrant tropical escape, blending old-school charm with island fun.
Plunge into a retro Polynesian paradise where exotic rums and classic tiki cocktails create a festive atmosphere. This upscale yet playful venue adds a splash of color and excitement, keeping your night fresh and the drinks full of imagination.
The next stop is a straightforward walk back into the Loop's historic heart, moving from tropical vibes to an iconic Chicago classic.
Wind down at this Chicago favorite, where hearty American dishes pair with craft brews in a warm, welcoming space. It's the perfect way to cap off the night, with familiar flavors and a convivial crowd that's great for sharing stories and enjoying those last drinks.
This marks the end of the journey, smack in the middle of the Loop, so you can either keep the night going or head home feeling fulfilled.
From those sky-high cocktails to the thrill of a hidden speakeasy, tropical twists, and that classic pub feel, this Chicago Loop adventure delivers a night full of flavor and excitement. Whether you're hanging with friends or making new ones, each stop brings a fresh wave of fun. Ready to make it your own? Grab your crew, slip on some comfy shoes, and let the Loop's vibrant cocktail scene take the lead.
Crawl Map