đź“… Open Today: Crawl likely open on Sundays
Explore Chicago’s best small pubs and hidden watering holes on this lively pub crawl. Visit three unique venues—Dram Shop, Duffy's Tavern and Grille, and Roebuck—each offering cozy atmospheres, sports on TV, jukebox tunes, and delicious bar food. From rustic craft cocktails and microbrews to tasty thin-crust pizzas, these spots are perfect for a fun night out with friends. Discover the city’s best-kept secrets and enjoy a memorable evening full of good drinks, great vibes, and local charm.
Last updated: June 2025
Kick off your night in Chicago’s Lake View East neighborhood with a laid-back bar hop that cranks up the energy and social fun from the get-go. Begin at Dram Shop, where an epic whiskey lineup pairs with jukebox jams in a super authentic tavern vibe—ideal for kicking back, chatting with pals, and getting the good times rolling. Next, swing over to Duffy’s Tavern and Grille, where tasty bar eats meet live music that lights up the room, pulling you right into the heart of the neighborhood’s buzzing nightlife. Wrap up the fun at Roebuck, a cozy, rustic-chic hangout where local microbrews, craft cocktails, and thin-crust pizzas come together for a chill, satisfying end that mixes character and comfort with every sip and bite.
Kick things off at Dram Shop, a classic Chicago tavern with a killer whiskey selection and a lively jukebox, setting a fun, sociable vibe for the night ahead.
The next spot is just a brisk 15-minute walk south, giving you a great opportunity to soak in the lively Lake View East streets on your way to Duffy’s Tavern and Grille.
Duffy’s amps up the adventure with its mix of spirited live music and hearty bar fare, injecting fresh energy and a festive feel that keeps the good times flowing.
The next stop is an easy 10-minute walk north along Broadway, a buzzing path that leads you straight to Roebuck’s warm, rustic-chic atmosphere.
Wrap up your bar hop at Roebuck, where craft cocktails, house-brewed beers, and wood-fired pizza create a welcoming, rustic spot to savor the night’s final highlights with ease.
This marks the end of the hop, so take your time to settle in and enjoy those last tasty bites and drinks.
This Lake View East bar hop mixes genuine tavern charm, live music excitement, and tasty craft treats into one epic night out. Whether you’re a local or a visitor hunting for Chicago’s vibrant scene, these spots hit the sweet spot for casual hangs and flavor-packed discoveries. Grab your crew, slip on some comfy shoes, and jump into the rhythm of Lake View East— where every sip and step adds to the story of your evening.
Crawl Map