Best Whiskey & Bourbon Cocktails in West Town, Chicago
The 3 top-rated whiskey & bourbon cocktails in West Town, Chicago, ranked by flavor score.
The top choice is manhattan at The California Clipper (1002 N California Ave), with a flavor score of 85 out of 100 from 17 diner ratings. Flavor scores come from what real diners say in their reviews. Last updated August 27, 2026. How flavor scores work →
Best Whiskey & Bourbon Cocktails across Chicago→- Ranked #1At The California Clipper1002 N California Ave
The Manhattan is praised for its well-mixed, tasty flavor and the addition of a whiskey-soaked cherry.
- Ranked #2At Matchbox Bar768 N Milwaukee Ave
A well-balanced Manhattan made with Bulleit rye and garnished with brandy-soaked cherries earns high praise for its rich flavor.
- Ranked #3At Chop Shop2033 W North Ave
The Manhattan features a smooth blend with cherry vanilla simple syrup and real black cherry garnish, earning high praise from many.
Which one is the GOAT?
You can crown one per category, so choose wisely.