In a city where faded Old Style signs swing outside of beloved dive bars and lines snake around the block at trendy cocktail lounges, the best bars in Chicago act as meeting places, date locales and venues for celebrations.
With so many great places to grab a beverage, the list of our all-time favorite bars around town is expansive—and inclusive of taprooms at Chicago breweries, sultry wine bars uncorking bottles of reds and whites, and the finest cocktail bars Chicago has to offer. In a metropolis packed with places to sip and swirl, these watering holes shine even brighter and boozier. Take a look at the best bars in Chicago and find the perfect destination for your next night out.
Best Chicago bars at a glance:
- 🎶 For live music: Green Mill – Historic jazz lounge with nightly performances (Uptown)
- 🍹 For extravagant cocktails: The Aviary – Theatrical cocktail experience (West Loop)
- 😘 For date night: Lazy Bird – Basement bar with intimate vibes and live sets (West Loop)
- 🎉 For group celebrations: Three Dots and a Dash – Tiki cocktails with extravagant garnishes (River North)
- 🍸 For rare spirits: Billy Sunday – Amaro-focused drinks with unusual ingredients (Logan Square)
Updated May 2026: Sometimes you want to let loose in a loud bar after a long week, and sometimes you just want to cozy up at a dive bar with only a beer and your thoughts. No matter the occasion, the best bars in Chicago promise the best of whatever experience you’re seeking. In this updated list of the must-hit spots, we’ve laid out a guide to the city’s finest watering holes, from sprawling rooftop bars to storied dives and low-key basement bars.
Time Out has also instituted a sitewide change in review policies. Our food and drink venues included in guides now have star ratings, with five stars corresponding to “amazing,” four to “great” and three to “good,” and we’ve also standardized how most listings are structured. For more on our new policies, feel free to check out How we review at Time Out.
RECOMMENDED: