Bar hopping isn’t just another weekend activity in Chicago — it’s an experience. Chicago has earned its place as one of the country’s best cities for a night out. Whether you’re a local looking to rediscover your neighborhood or a tourist searching for the city’s best-kept secrets, bar hopping in Chicago promises an adventure.
This guide will walk you through Chicago’s impressive bar scene. We'll share practical tips for a successful experience and recommend routes and venues that truly capture the city's heartbeat.
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Why Bar Hopping in Chicago Is a Must-Do
What makes bar hopping here special is the city’s eclectic mix of neighborhoods, each offering its own distinct vibe. From high-energy sports bars to moody speakeasies, lively rooftop bars, and craft breweries, you’ll find variety at every corner.
The city’s reputation as a culinary and hospitality hub also ensures that each bar you visit is serving more than just drinks. Many venues boast expertly crafted cocktails, microbrews brewed in-house, and bar snacks that rival full dinners.
Interested in a guided experience? Book a Prohibition Speakeasies Bus Tour or Walking Tour.
Chicago’s Neighborhoods and Bar Scene
Every Chicago neighborhood has its own personality, and that extends to its bars. Here’s an overview to help you pick the best areas for your night out:
Wrigleyville
Known for its proximity to Wrigley Field, Wrigleyville is the go-to for sports fans. The streets are lined with high-energy sports bars, karaoke spots, and rooftop lounges that perfectly amplify the game-day excitement.
Bars to Visit:
- Murphy’s Bleachers for classic pre-game vibes.
- Sluggers for its iconic batting cages and energy on Clark Street.
- Bamoboo Club for Instagrammable cocktails and themes.
West Loop
West Loop is home to upscale cocktail bars and chic lounges that attract foodies and trend-setters. It’s the perfect neighborhood if you like your drinks to come with a side of sophistication.
Bars to Visit:
- Aviary for inventive cocktails that are as much about art as they are about taste.
- Blind Barber for a speakeasy experience hidden behind a functioning barbershop.
- Lazy Bird for a cozy, jazz-inspired ambiance.
Logan Square
Casual, artsy, and a little offbeat, Logan Square offers a mix of hip microbreweries, laid-back dives, and bars specializing in craft cocktails.
Bars to Visit:
- The Whistler for its rotating cocktail menu and intimate performances.
- Scofflaw for gin lovers—it’s their specialty.
- The Owlfor its 4:00 AM closing time and live music sets.
River North
River North thrives on an energetic nightlife scene filled with trendy rooftop bars, dance-friendly spots, and lounges perfect for groups.
Bars to Visit:
- Three Dots and a Dash for an unforgettable tiki bar experience.
- Joy District Rooftop for unparalleled views and a lively atmosphere.
- Underground for late-night dancing and drinks.
Wicker Park
This eclectic neighborhood is a magnet for young professionals, artists, and lively crowds. Expect dive bars, live music venues, and trendy spots with craft beers.
Bars to Visit:
- Queen Mary for an elegant, British-inspired pub experience.
- Emporium for a lively barcade scene with vintage arcade games and craft beers.
- Ina Mae for a taste of New Orleans with its delicious Cajun food and cocktails.
Lincoln Park
A popular destination for DePaul University students, Lincoln Park offers a variety of bars and pubs to explore, from sports bars to upscale lounges.
Bars to Visit:
- The Red Lion Pub for an authentic British pub experience and good food.
- Armitage Alehousefor a laid-back atmosphere and a wide selection of beers.
- Old Town Ale House for a dive bar experience with local art and cheap drinks. It's also a favorite of the late Anthony Bourdain!
- Replay Lincoln Park for an arcade bar with a rotating selection of craft beers.
Tips for a Successful Bar-Hopping Night
Here are a few pro tips and tricks for bar hopping in Chicago:
Plan your route
Picking neighborhoods or bars ahead of time can save you from wandering aimlessly in the cold—or trying to decide after a couple of drinks. Aim for areas like Wicker Park or Logan Square, where bars are walkable, or keep Uber/Lyft handy for hopping between farther locations.
Budget wisely
Bar hopping can get pricey, especially with Chicago’s cocktail culture. To make your night wallet-friendly, seek out happy hours or drinking establishments with specials. Sharing apps and splitting large cocktails or pitchers can also stretch your budget while keeping the fun flowing.
Stay safe
With drinks flowing, it’s essential to stay safe.
- Keep yourself hydrated by alternating cocktails with glasses of water.
- Make sure to eat beforehand or grab a snack during the night. Chicago bars often have excellent bar food, so take advantage!
- If you're traveling as a lone wolf, update a trusted friend with your plans and locations.
Dress for the occasion
Chicago weather can be unpredictable, so dress appropriately. Especially if you’re bar hopping on foot. Comfortable shoes are non-negotiable, and a warm coat is a must during the city’s colder months.
Final Thoughts for Your Perfect Bar Crawl
Chicago’s bar-hopping scene is one of its greatest treasures. It offers something for everyone, from beer lovers and cocktail connoisseurs to sports fans and music fans. With a bit of planning and this guide in hand, your next night out in the city is bound to be unforgettable. Don't forget to try a Chicago Handshake!
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