đź“… Open Today: Crawl likely open on Mondays
Discover the vibrant Chicago cocktail scene with our exclusive bar crawl featuring three amazing venues. Start at Brando's Speakeasy, a vintage lounge with secret vibes, karaoke, and dancing. Then head to RAISED, a stylish rooftop bar offering craft cocktails and skyline views perfect for sunset sips. Finish the night at Kasey's Tavern, a lively pub with great drinks and sports on the TVs. Whether you're into hidden speakeasies, rooftop lounges, or classic pubs, this crawl has something for every night owl looking for fun and flavor in the Windy City!
Last updated: June 2025
Dive right into the heart of Chicago’s Loop on this quick cocktail bar crawl, packed with vibrant energy and those unmissable social vibes. Start tucked away in the sultry, vintage charm of Brando’s Speakeasy, where you’ll find expertly crafted drinks, live karaoke thrills, and a dance floor that’s begging to be hit. Then, head up to Raised, a chic indoor-outdoor rooftop spot with stunning river and skyline views, plus inventive cocktails and shareable bites that keep the night buzzing. Finally, wind down at Kasey’s Tavern, a go-to Chicago pub with a solid beer selection and that warm, welcoming atmosphere— the ideal place to cheers with new pals and swap stories. This whole crawl is all about excitement and easygoing adventure, blending unique spots into one smooth night out.
As the crawl’s lively starting point, Brando’s Speakeasy pulls you into vintage glamour and karaoke fun, kicking off the night with top-notch cocktails and a buzzing dance floor.
The next stop is a brisk, scenic walk to Raised rooftop, offering a refreshing shift from cozy vibes to open-air views.
RAISED amps up the energy with its trendy indoor-outdoor setup, panoramic city views, and a craft cocktail menu made for sharing, turning the night into a fun, elevated urban bash.
The next stop is a lively stroll through the Loop’s busy streets, leading you to Kasey’s Tavern’s charming, laid-back spot.
Kasey’s Tavern wraps up the crawl with its classic Chicago pub charm, serving up a great beer selection and a welcoming space to end the night with easy chats and local flavors.
The crawl ends here, giving you the perfect vibe to look back on the night’s highlights.
This quick Chicago Loop Cocktail Bar Crawl is your go-to for an epic night full of dynamic energy, killer views, and real local tastes. Whether you’re singing karaoke, enjoying rooftop sips, or checking out a pub’s beer lineup, each spot flows seamlessly into the next for a spirited adventure. Grab your crew, plot your path, and dive into the Loop’s cocktail scene— Chicago’s nightlife is ready to wow you.
Crawl Map