Best Cocktail Bars in Old Town
Updated June 16, 2026 · Ranked by combined rating and review volume
Where to find the best cocktail bars in Old Town
The VIG Old Town offers a vibrant, upbeat atmosphere perfect for any occasion, from lively happy hour gatherings to delicious weekend brunches. This hip, warehouse-style gastropub is renowned for its attentive service and a menu that truly impresses, featuring standout items like their unforgettable steak sandwich and delectable lobster deviled eggs. Guests consistently praise the excellent food, solid happy hour deals on cocktails and bites, and the welcoming vibe.
Dearly Beloved
Dearly Beloved is an exquisite cocktail lounge that captivates with its edgy yet classy decor, featuring plush velvet seating and a sophisticated, uncrowded atmosphere. Patrons rave about the top-tier drinks, including unique smoky concoctions, complemented by delicious appetizers like caviar and pho soup. The exceptional customer service, from the warm welcome to attentive staff like Genesis, ensures every visit is a breathtaking and memorable experience.
Winnie's Chicago
Winnie's Chicago is quickly becoming a beloved Old Town staple, celebrated for its fantastic atmosphere, especially for sports enthusiasts with TVs galore, and incredibly friendly staff who treat everyone like family. Beyond the lively game-day vibe, this spot shines with an amazing food menu that offers surprisingly healthy options alongside classic bar favorites like their perfect fries and a unique club sandwich. Guests consistently rave about the quick drink service, even when packed, and the genuine care from the owner.
Old Town Ale House is a true Chicago institution, a laid-back, cash-only dive bar that has retained its old-school charm since 1958. It's renowned for its storied past, classic jukebox tunes, and unique, often humorous, artwork by the owner that sparks conversation. Patrons appreciate the cheap drinks, friendly bartenders who craft excellent Irish mules, and the unpretentious atmosphere, making it a perfect pre-show stop near Second City.
LUXBAR offers a refined yet inviting atmosphere, boasting a sophisticated wood-and-brass, two-level setting complete with a charming patio. It's a consistently recommended spot where guests can enjoy top-notch drinks and a diverse menu featuring everything from sliders and steaks to fresh salads. The exceptional service truly stands out, with staff like Emma and Ryan ensuring every diner feels welcomed and well-cared for, making for a pleasant and attentive dining experience.
Contenders
Places submitted by the community. The top contender with more points than #5 gets promoted.
How we ranked the best cocktail bars in Old Town
Every place on this list is scored by a Bayesian weighted formula combined with a volume bonus. It rewards consistent positive feedback at scale, not just a high average rating — a 4.9-star place with 12 reviews ranks below a 4.6-star place with 800.
score = (v / (v + m)) × R + (m / (v + m)) × C + γ × log₁₀(v)
The prior m adapts to each neighborhood: it's the median review count among local candidates. So 200 reviews counts as “small sample” in dense markets like the West Village, but “solid” in quieter neighborhoods. Places with extreme review volume that clearly dominate their peers are promoted to #1. No paid placements — every spot earns its position via the public data.
Frequently asked about Old Town cocktail bars
What is the highest-rated cocktail bar in Old Town?
Winnie's Chicago has the highest Google rating in our list of the best cocktail bars in Old Town, with 5.0 stars across 236 reviews.
Which cocktail bar in Old Town has the most reviews?
The VIG Old Town has the most reviews of any cocktail bar on this list — 3,785 ratings averaging 4.7 stars on Google.
How are the best cocktail bars in Old Town ranked?
Each place is scored using a Bayesian weighted formula that combines its average Google rating with its review count. This pulls small-sample places toward the local mean — so a 4.9-star spot with 12 reviews is ranked below a 4.6-star spot with 800 reviews. Volume and consistency matter, not just an inflated average.
When was this ranking last updated?
This ranking of the best cocktail bars in Old Town was last refreshed in June 2026 using the latest Google ratings and review counts. Restaurants and bars change constantly — always verify hours and current status before visiting.
Why isn't my favorite cocktail bar on the list of best cocktail bars in Old Town?
To be considered, a place needs enough Google reviews for the rating to be statistically meaningful (at least 5 reviews, ideally 25+). Newer or hyper-local spots can be excellent but score lower until enough people review them. Boundaries also matter — a spot just outside the Old Town area may show up on a neighboring ranking instead.