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.
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)
October 15, 2025: This month, we've refined the list to an exclusive ranking of the top 24 absolute best bars in Chicago. This expanded ranking features a trio of new entries: Old Town Ale House, which is by no means new but certainly deserves a spot on this list; Gus' Sip & Dip, Lettuce Entertain You's new-ish walk-in-only watering hole inside the former Hub 51 space (RIP); and Cindy's, which was recently named the best rooftop restaurant in Chicago. There's a bevy of hotspots to grab a bev in this town, 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.
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.
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