đź“… Open Today: Crawl likely open on Mondays
Discover Chicago’s best hidden and historic pubs on this unforgettable crawl! Start at Brando's Speakeasy, a cozy vintage space with drinks, karaoke, and dancing in a secretive setting. Then, head to Kasey's Tavern, a classic sports bar serving top-shelf beers and catching all the games. Finish at Miller's Pub, a warm, American-style pub serving craft brews and hearty bites since 1935. Perfect for a fun night out filled with great drinks, music, and good vibes across three iconic venues!
Last updated: June 2025
Hey, ready to dive into the fun of Chicago's Loop pub scene? This compact adventure kicks things off with the hidden charm of Brando’s Speakeasy, where vintage vibes mix with lively karaoke and dancing to get the night pumping. Then, soak up the energy at Kasey’s Tavern, a go-to spot for an epic beer selection and that classic game-day buzz that keeps everyone chatting. Finally, wind down at Miller’s Pub, a beloved downtown hangout serving up hearty eats and craft brews in a cozy atmosphere that makes you want to linger. It's all about weaving together cool spots for a seamless night of laughs, great drinks, and good times right in the heart of the city.
Kick off your night behind the sneaky doors of Brando's Speakeasy, where old-school glamour meets a fun karaoke stage. This place gets everyone hyped with its mix of retro charm and upbeat dancing, making it the perfect spot to warm up and spark some impromptu sing-alongs.
The next stop is just a short, lively walk through Chicago’s buzzing streets, keeping the good vibes flowing as you head to Kasey’s Tavern.
Jump into the lively vibe at Kasey’s Tavern, where a killer lineup of craft and international beers pairs with big screens showing all the top sports action. It's a welcoming hangout that builds on the fun from Brando’s, adding a competitive edge and plenty of chances to chat with new friends.
The next stop is a quick, energizing stroll deeper into the Loop’s core, leading to classic pub grub and easygoing chats at Miller’s Pub.
Wrap up your adventure at Miller’s Pub, a true Chicago favorite where solid American dishes and tasty craft brews keep the energy high. This warm, friendly spot is ideal for toasting your night of exploration with good food, drinks, and that timeless Loop charm.
This marks the end of the crawl, leaving you in a prime spot to keep the night going or head out with some awesome memories.
From those secretive speakeasy feels to hearty pub toasts, this Chicago Loop pub hop serves up a tight, high-energy ride through some of the city's most fun drinking spots. Whether you're belting out karaoke hits, clinking glasses over brews, or digging into iconic Chicago eats, every stop adds to the excitement. So, grab your friends, hit the streets, and let the Loop's lively spirit lead you to an epic night you'll talk about for ages.
Crawl Map