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Hidden Gems: Top 10 Bars in Chicago’s Old Town You Must Visit

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by Torrie Pitzer

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Chicago's Old Town is a lively neighborhood filled with history, charm, and some of the best bars in the city. Whether you're a local or just visiting, this area offers a unique mix of cozy pubs, trendy cocktail spots, and classic taverns. Each bar has its own vibe, making it a perfect place to unwind after a day of exploring. From craft beer enthusiasts to cocktail lovers, there's something for everyone. The vibrant atmosphere and friendly locals make it easy to feel at home. So, if you're looking to experience the best of Chicago's nightlife, Old Town is the place to be. Get ready to sip, savor, and enjoy the hidden gems that make this neighborhood a must-visit destination.

Discover Chicago's Old Town Nightlife

Chicago's Old Town is a vibrant neighborhood brimming with history, charm, and some of the city's best bars. Whether you're a local or a visitor, these spots offer unique experiences that are sure to make your night memorable. Let's dive into the top 10 bars you must check out.

Classic Pubs with a Twist

Old Town is home to several classic pubs that offer more than just your average pint. These places blend tradition with a modern flair, creating an atmosphere that's both cozy and exciting.

  1. The Old Town Ale House
    Known for its eclectic decor and lively crowd, this bar has been a staple since 1958. It's the perfect spot for those who appreciate a dive bar vibe with a touch of history.

  2. Twin Anchors Restaurant & Tavern
    Famous for its ribs and classic cocktails, this spot has been serving patrons since 1932. It's a must-visit for anyone who loves a good meal with their drink.

Craft Cocktails and Chic Ambiance

For those who prefer a more refined drinking experience, Old Town offers several bars that specialize in craft cocktails and chic settings.

  1. The VIG Chicago
    This bar combines sports and sophistication, offering a wide range of craft cocktails in a stylish setting. It's a great place to catch a game while sipping on something fancy.

  2. The Up Room
    Located atop The Robey, this rooftop bar provides stunning views of the city skyline. Enjoy a handcrafted cocktail while taking in the breathtaking scenery.

Hidden Speakeasies

If you're in the mood for something a bit more secretive, Old Town has a few hidden speakeasies that will transport you back in time.

  1. The Violet Hour
    Behind an unmarked door lies this elegant speakeasy known for its inventive cocktails and intimate atmosphere. It's a hidden gem that's worth the search.

  2. The Drifter
    Tucked beneath the Green Door Tavern, this speakeasy offers a rotating menu of unique drinks and live performances. It's a place where history and creativity collide.

Lively Music Venues

For those who love live music, Old Town has bars that double as music venues, offering a chance to enjoy great tunes with your drink.

  1. The Second City
    While known for its comedy shows, this venue also features a bar where you can enjoy a drink before or after a performance. It's a lively spot with plenty of entertainment.

  2. Old Town School of Folk Music
    This venue offers a bar where you can grab a drink while enjoying live folk music performances. It's a unique experience that combines music and community.

Cozy Hangouts

Sometimes, you just want a laid-back spot to relax with friends. Old Town has several cozy bars perfect for unwinding.

  1. Corcoran's Grill & Pub
    With its warm atmosphere and friendly staff, this bar is a great place to kick back and enjoy a casual night out. It's a neighborhood favorite for a reason.

  2. Woodie's Flat
    Known for its laid-back vibe and extensive beer selection, this bar is ideal for those looking to relax and enjoy good company. It's a welcoming spot for all.

Discovering Old Town's Unique Bars

Chicago's Old Town offers a vibrant mix of bars that cater to every taste. From the historic charm of Old Town Ale House to the modern vibes at The VIG, each spot provides a unique experience. The Fireplace Inn is perfect for those who enjoy a cozy atmosphere, while Woodie's Flat offers a lively setting for sports enthusiasts. For cocktail lovers, The Rabbit Hole and The Glunz Tavern serve up creative drinks that delight the senses. Corcoran's Grill & Pub and Benchmark are ideal for social gatherings with friends. Happy Camper and Broken English Taco Pub bring a fun twist with their themed interiors and delicious bites. Exploring these hidden gems in Old Town not only promises great drinks but also a chance to soak in the local culture. Whether you're a local or a visitor, these bars are worth a visit.