Top 10 Essential Bars in Chicago’s Old Town
Explore the most iconic and beloved bars in Chicago’s Old Town, from historic jazz haunts to cozy cocktail lounges.
Chicago’s Old Town is a fascinating neighborhood brimming with historic charm, lively streets, and one of the city’s most beloved bar scenes. Whether you’re searching for classic cocktails in atmospheric settings, eager to hear jazz in a space with gangster-era mystique, or craving craft beer and new American bites, Old Town offers something for every palate and mood. This guide introduces ten of the most essential bars to experience in Old Town—each with its own unique backstory, style, and specialty drinks.
1. The Old Town Ale House
The Old Town Ale House is the epitome of a neighborhood dive bar, renowned for its irreverent art, unpretentious comfort, and connection to Chicago’s comedy scene. Open since 1958, the Ale House is an institution where laughter, local history, and cheap drinks flow in equal measure. Famed for its eclectic crowd, from writers and comics to neighborhood regulars, and satirical paintings that adorn the walls, it’s a favorite haunt of both locals and visiting celebrities.
- Atmosphere: Unfiltered, quirky, and fiercely independent.
- Signature Experience: Absorb Chicago’s local color over a beer or whiskey, surrounded by cheeky political cartoons and portraits.
- Tip: A visit after catching a show at the neighboring Second City is a true Old Town tradition.
2. The House of Glunz
Steeped in history, The House of Glunz opened its doors in 1888 and still feels like a step back in time. This wine and spirit emporium doubles as a sophisticated bar, offering a unique opportunity to sample rare vintages, fine whiskeys, and perfectly crafted cocktails. The art-glass mahogany bar, original fixtures, and Old World service transport guests to Prohibition-era Chicago, making it a must-see for history lovers and oenophiles alike.
- Atmosphere: Classic, elegant, and historic.
- Signature Experience: Enjoy a glass of carefully curated wine or rare bourbon in an exquisitely preserved late 19th-century setting.
- Tip: The knowledgeable staff is happy to recommend pairings or share stories about the bar’s storied past.
3. Old Town Pour House
Old Town Pour House is a modern gastropub boasting one of the most impressive draft beer selections in Chicago, with over 90 rotating taps. The massive, vibrant space is perfect for gathering with friends, hosting an event, or simply exploring new craft brews. Complement your drink with delicious American fare and enjoy sports on wall-to-wall televisions.
- Atmosphere: Contemporary, bustling, and social.
- Signature Experience: Tap into rare local, national, and international beers accompanied by upscale pub classics.
- Tip: Sample a beer flight to discover new favorites or enjoy happy hour specials during the week.
4. Marge’s Still
Marge’s Still is one of Chicago’s oldest continuously operating bars, tracing its roots back to the Prohibition era. With its elegant tin ceiling, exposed stone walls, and vintage ambiance, Marge’s combines a storied past with innovative cocktails and comforting New American bites. Legend has it that tunnels beneath the bar once aided bootleggers and outlaws in eluding authorities.
- Atmosphere: Cozy, romantic, and steeped in lore.
- Signature Experience: Savor a modern cocktail in a space that feels both timeless and intimate.
- Tip: Try the seasonal cocktails, often inspired by fresh, local ingredients.
5. The VIG Chicago
The VIG offers a playful, vintage sports-club vibe with a chic, contemporary twist. The interior features leather banquettes, retro decor, and a large mural inspired by the city’s rich athletic history. The menus are equally creative, from inventive craft cocktails to shareable bar snacks and hearty brunch options. The VIG is ideal for groups, game days, or an upbeat night out.
- Atmosphere: Sporty, energetic, and stylish.
- Signature Experience: Enjoy a round of specialty cocktails and modern comfort food in a lively setting.
- Tip: Arrive early during big games to snag a seat with optimal TV viewing.
6. Topo Gigio Ristorante
While most famous for its traditional Northern Italian menu, Topo Gigio also shines as a bar destination. The intimate, wood-paneled bar area is perfect for lingering over Italian aperitifs, robust wines, and classic cocktails. Step in for an authentic espresso martini, a glass of Chianti, or simply to enjoy people-watching on Well Street alongside delicious antipasti.
- Atmosphere: Warm, rustic, and authentically Italian.
- Signature Experience: Sip on a Negroni or Campari spritz before or after dinner.
- Tip: Order a selection of appetizers to pair with your drink for the full Italian experience.
7. Zanies Comedy Club Bar
A Chicago comedy mainstay since 1978, Zanies is not only a legendary performance venue—it’s a beloved watering hole for comics and comedy fans alike. The intimate bar area is a great spot to recap the night’s jokes and connect with emerging talent over a well-poured drink or a classic beer. Zanies balances no-frills charm with a sense of cultural history, attracting both locals and out-of-towners for a memorable night out.
- Atmosphere: Playful, casual, and buzzing with laughter.
- Signature Experience: Enjoy a drink before, during, or after a standout comedy show.
- Tip: Shows often sell out—arrive early for best bar seating and preshow atmosphere.
8. Declan’s Irish Pub
Declan’s Irish Pub brings true Dublin spirit to Old Town, delivering a warm welcome alongside hearty fare and a formidable selection of whiskeys and ales. The wooden bar, cozy booths, live music, and Guinness on tap anchor an environment where conversation flourishes. Declan’s is particularly popular for St. Patrick’s Day festivities, but its authentic hospitality draws visitors all year round.
- Atmosphere: Inviting, festive, and authentically Irish.
- Signature Experience: Sip a perfectly poured Guinness or sample Irish whiskey flights surrounded by live folk music.
- Tip: Ask about traditional Irish breakfast during weekend brunch hours.
9. The Fireplace Inn
A neighborhood staple since 1969, The Fireplace Inn is famed for its generous barbecue plates, welcoming staff, and vibrant bar scene that bridges generations. The large stone fireplace and nostalgic décor evoke a sense of classic Americana, making it a favorite stop for both casual nights out and group celebrations. Signature drinks include classic American beers, house margaritas, and boozy milkshakes.
- Atmosphere: Laid-back, cheerful, and community-focused.
- Signature Experience: Enjoy ribs or burgers with a frosty pint or specialty cocktail by the fire.
- Tip: The outdoor patio is perfect for summer evenings and people-watching along Wells Street.
10. 80 Proof
80 Proof stands out for its energetic, party-centric vibe: think bottomless brunches, themed DJ nights, late-night dancing, and creative cocktails served over three distinct levels. Known for social events and eclectic music, 80 Proof draws a lively mix of locals and urban explorers throughout the week. The rooftop bar provides sweeping views of Old Town and a refreshing change of perspective for cocktail enthusiasts.
- Atmosphere: Modern, lively, and multi-level.
- Signature Experience: Join for themed brunch, or dance into the night on weekends.
- Tip: Rooftop seating and group reservations are highly sought after—book ahead for special occasions.
Notable Features of Old Town’s Bar Scene
- Historic Roots: Many bars here operated as speakeasies or gathering spots for artists, musicians, and activists during the 20th century.
- Cultural Landmarks: Several venues, like Zanies and The Old Town Ale House, are woven into Chicago’s entertainment and artistic legacy.
- Diverse Experiences: From jazz and comedy to sports and fine wines, each bar brings its own flavor to the neighborhood.
Comparing Old Town’s Top Bars
| Bar | Best For | Signature Drink or Feature |
|---|---|---|
| Old Town Ale House | Dive Bar Ambiance & Comedy Lovers | Classic Beer, Irreverent Art |
| House of Glunz | History Buffs & Wine Enthusiasts | Rare Wines, Old-School Whiskeys |
| Old Town Pour House | Craft Beer & Sports | Wide Beer Selection |
| Marge’s Still | Romance & Vintage Charm | Seasonal Cocktails |
| The VIG Chicago | Groups & Game Day | Modern Cocktails |
| Topo Gigio | Wine Aficionados | Italian Wines, Aperitifs |
| Zanies Comedy Bar | Entertainment & Comedy Fans | Classic Drinks, Comedy Shows |
| Declan’s Irish Pub | St. Patrick’s Day & Irish Fare | Guinness, Irish Whiskey |
| Fireplace Inn | BBQ & Family Gatherings | Burgers, Cocktails, Beer |
| 80 Proof | Nightlife & Brunch Parties | Craft Cocktails, Rooftop Views |
What Makes Old Town Unmissable for Bar Lovers?
Old Town’s mix of old-school character, dynamic new venues, and a rich cultural backdrop creates a bar-going atmosphere found nowhere else in Chicago. Whether you’re seeking storied taverns where history lingers in the air, or vibrant destinations for party-ready crowds, you’ll find your perfect hangout in Old Town.
Frequently Asked Questions (FAQs)
Q: Are these bars suitable for visitors new to Chicago?
A: Absolutely. Each bar listed offers a unique introduction to Chicago’s history, hospitality, and nightlife culture. Whether you love classic dives or upscale cocktail lounges, you’ll find something memorable in Old Town.
Q: Do Old Town bars offer live entertainment?
A: Yes. Venues such as Zanies Comedy Club and The Old Town Ale House frequently feature live performances—comedy, music, and open-mic events are all popular across the neighborhood.
Q: Is there a dress code at these bars?
A: Generally, Old Town bars maintain a casual to smart-casual dress code. Upscale venues or bars with special events may require dressier attire on weekends—always check ahead if you’re planning a night out.
Q: Are reservations necessary?
A: Most bars accept walk-ins, but reservations are highly recommended for large groups, brunches at 80 Proof, or during sporting event nights at The VIG or Pour House.
Q: What is the best time to visit Old Town’s bars?
A: Weekday evenings offer a relaxed vibe, while weekends see more spirited crowds, live events, and themed parties. For a truly local experience, explore during the annual Old Town Art Fair or St. Patrick’s Day celebrations.
