The cozy, all-season crown jewel of Time Out Market Chicago is anchored by a sprawling bar that serves a curated selection of wines, beers and signature cocktails. If the sun is shining, wander outside with a drink to take in skyline views on the breathtaking terrace.
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 extra bright and boozy. Take a look at the best bars in Chicago and find the perfect destination for your next night out.
RECOMMENDED: The best whiskey bars in Chicago
August 2025: This month, we've refined the list to an exclusive ranking of the top 20 absolute best bars in Chicago. You might notice this list is missing one of the city's most iconic cocktail institutions, The Violet Hour, which unfortunately had its final curtain call this summer after 18 headline-making years. Luckily, there's a bevy of other hotspots to grab a bev. So sip your way through these top spots (not all in one night, please), and discover the libations that have put Chicago on the map as a world-class mixology hub.
Curious about how we narrowed down this list to just 20 spots? Check out how we curate and review at Time Out.