đź“… Open Today: Crawl likely open on Sundays
Join us on a vibrant cocktail bar crawl through Chicago’s coolest spots! From cozy, tucked-away watering holes with sports on TV and vintage jukeboxes to intimate, gay-friendly lounges with vintage decor and DJs, this crawl has it all. Discover the literary-themed Irish pub with leather banquettes and an extensive beer list, or enjoy craft cocktails and house microbrews paired with delicious thin-crust pies. Perfect for a fun, unforgettable night out with friends!
Last updated: June 2025
Kick off an exhilarating night in Chicago’s Lake View East, where every sip feels like a story waiting to unfold and each stop cranks up the fun. This laid-back cocktail hop guides you from a cozy, whiskey-packed spot with that classic tavern charm to a stylish lounge with vintage vibes and DJ beats that get the energy flowing. Then, soak in the literary flair and hearty eats of an upscale Irish pub, before ending with rustic-chic vibes, killer craft cocktails, and wood-fired pizzas. It's all about exploring cool atmospheres, sparking easy chats, and keeping the adventure alive with bold tastes and lively crowds.
Launch your evening at Dram Shop, where the old-school tavern vibe meets an impressive whiskey lineup. Friendly bartenders and a lively jukebox keep things warm and inviting, setting a fun, spirited tone that gets everyone connecting right away.
The next spot is just a short, easy stroll north on Broadway, keeping the good times rolling as you head to a sleek, atmospheric cocktail lounge.
Step into Wang’s for a smooth transition to sophistication, with vintage Chinese-inspired decor, dim lights, and curated DJ tracks creating a cozy yet upbeat space. Here, classic and creative cocktails blend seamlessly for a memorable vibe.
The next stop is a quick, breezy walk south along Broadway, adding a dash of excitement as you approach a literary-inspired Irish pub.
At Wilde, enjoy the blend of upscale Irish pub elegance and modern American dishes – think plush seats and a great beer selection that sparks lively chats and group energy. It's all about that comforting, sophisticated twist on pub fun.
The next stop is a short, welcoming walk further south on Broadway, building anticipation for a relaxed yet vibrant spot with a foodie edge.
Wrap up your night at Roebuck, where rustic-chic style meets craft cocktails and house-brewed beers, paired with artisanal thin-crust pizzas for a cozy, energetic finish. It's the perfect spot for lingering conversations and making memories.
This marks the end of the crawl – a great spot to unwind, soak in the night's highlights, and savor the local flavors.
This Lake View East cocktail hop is your go-to for a night packed with personality, flavor, and that easy social buzz. From the welcoming charm of a classic tavern to the stylish beats of a vintage lounge, through the cozy comforts of an upscale pub to a rustic-chic pizza spot, every stop ramps up the fun and keeps things fresh. Get ready to treat your taste buds and lift your spirits – Chicago's cocktail world is primed for your next epic night out.
Crawl Map