Chicago's Old Town neighborhood boasts a rich history, and its vibrant bar scene perfectly reflects that heritage. From cozy, intimate pubs to lively, modern cocktail lounges, there's a watering hole for every taste in this charming area. This guide highlights 15 of the best bars in Old Town, offering a mix of classic Chicago experiences and unique finds. This list of the best bars in Old Town Chicago considers atmosphere, drinks, history, and overall experience.
Classic Chicago Charm: Old Town's Traditional Watering Holes
The North Pond
This isn't just a bar; it's a Chicago institution. The North Pond offers an upscale, sophisticated ambiance with a stunning patio overlooking a pond – a true oasis in the city. Their cocktail menu is extensive and innovative, utilizing seasonal ingredients. The North Pond is perfect for a romantic date night or a celebratory gathering.
The Pony Inn
A true Old Town staple, The Pony Inn exudes a classic Chicago tavern vibe. This cozy spot features a friendly atmosphere, affordable drinks, and a regular clientele who appreciate its down-to-earth charm. Expect a lively atmosphere on weekends, especially when live music is playing.
Old Town Ale House
This lively pub offers a wide selection of craft beers on tap, along with classic pub fare. The Old Town Ale House is a great place to catch a game, socialize with friends, or simply enjoy a relaxed evening. Its casual atmosphere makes it ideal for groups of all sizes.
Hidden Gems and Unique Experiences
The Purple Pig
While known for its Mediterranean-inspired tapas, The Purple Pig also boasts a fantastic wine list and a stylish bar area. The atmosphere is lively yet sophisticated, making it a versatile choice for a pre-dinner drink or a more substantial evening out.
Gibsons Bar & Steakhouse
A Chicago classic with an Old Town location, Gibson's offers a sophisticated atmosphere and an extensive cocktail list. The ambiance is upscale, and the service is impeccable, making it a perfect choice for a special occasion.
Benchmark
For a more modern, trendy bar experience, head to Benchmark. This stylish spot features creative cocktails, a sleek atmosphere, and an impressive selection of spirits. Their knowledgeable bartenders are always happy to recommend something new.
Lively Lounges and Late-Night Spots
The Second City
While primarily a comedy club, The Second City also features a bar that's a great place to grab a drink before or after a show. The atmosphere is lively and social, often filled with other theatre-goers and locals alike.
Kingston Mines
A Chicago blues institution, Kingston Mines offers a high-energy atmosphere and world-class music. The bar area is often crowded, but the energy is infectious, and the music is truly unforgettable.
The Green Mill Cocktail Lounge
Another legendary Chicago spot, The Green Mill boasts a long and storied history, steeped in jazz and literary lore. Enjoy live music, classic cocktails, and a unique atmosphere in this historic venue.
Dive Bars and Casual Hangouts
Butch McGuire's
A quintessential Chicago dive bar, Butch McGuire's offers a no-frills atmosphere, cheap drinks, and a friendly, unpretentious crowd. It's a great place to experience a truly authentic Chicago bar.
Schubert's
This iconic Old Town establishment has been a neighborhood favorite for generations. Schubert's offers a cozy atmosphere, classic cocktails, and a relaxed vibe. It's a perfect spot for a quiet drink or a casual get-together.
Unique & Thematic Bars
Blind Barber
This speakeasy-style bar is cleverly hidden behind a working barbershop. This unique concept adds to its charm, and the cocktails are top-notch. Expect a sophisticated atmosphere and a carefully curated drink menu.
Estereo
For those who enjoy a vibrant Latin American atmosphere, Estereo is the perfect choice. This lively bar offers delicious cocktails, a vibrant atmosphere, and regular live music.
Finding Your Perfect Old Town Bar
Choosing the right bar depends entirely on your preferences. Consider the following when planning your Old Town bar crawl:
- Ambiance: Do you prefer a cozy, intimate setting or a lively, bustling atmosphere?
- Drinks: Are you looking for a specific type of drink (e.g., craft beer, cocktails, wine)?
- Food: Do you want to enjoy food along with your drinks?
- Music: Do you prefer live music or a more relaxed atmosphere?
- Crowd: Are you looking for a specific type of crowd (e.g., young professionals, families, tourists)?
This guide provides a starting point for exploring the diverse and exciting bar scene in Old Town Chicago. Remember to check individual bar websites for hours of operation, specials, and reservation policies. Enjoy your Old Town pub crawl!
