AUTHOR BIO: With family spread across the Midwest and a job that has her in airports regularly, Jamie Dutton finds herself across the center of the U.S. regularly. She’s partial to BPTs a Bell's.
I don’t like bars, or at least I don’t like what most people mean when they say “bar.” Sticky floors. Music you can feel in your molars. That guy in a backwards Cubs hat yelling at his phone on speaker. If that’s your thing, great—Godspeed. But if the idea of a bar makes you instinctively look for the exit, you might just be going to the wrong ones.
This is a guide to the other kind of bar. The ones where the music never drowns out the conversation, where drinks come in actual glasses and not Solo cups, and where you could plausibly show up alone with a book and not feel like a weirdo.
After years frequenting Chicago bars, and often finding the exact kind of vibe I’m trying to avoid, I’ve found some that are elegant, some that are oddball, and some designed for people who appreciate a well-made drink in a space that doesn’t feel like a college basement. In other words: the bars for people who don’t like bars. Here then are the best bars in Chicago that won’t immediately make you want to ask for the check.
Andy’s Jazz Club
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This is one of the rare places where dinner and live jazz don’t feel like a forced pairing. The vibe is polished but relaxed, with nightly sets that include blues, Latin jazz, and big-band swing. It’s perfect for date night or anyone who wants to feel grown up for a couple hours.
The Aviary
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You’ll need a reservation and maybe a second mortgage, but The Aviary turns cocktails into performance art. The drinks involve smoked glass domes, centrifuged spirits, presentations that arrive in lab equipment, and, as pictured above, a branding iron as hot as Kendrick Lamar. This is, after all, a bar run by the folks behind Alinea, that beacon of molecular gastronomy. The Aviary is perhaps the only Chicago bar where you’ll feel underdressed in a suit.
Green Mill Cocktail Lounge
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This jazz lounge has been around since Capone and still hasn’t sold out. On any night you might find a full swing band, a beat poet, or a woman playing upright bass like her life depends on it. There’s no pretense here—just red booths, cheap whiskey, and a kind of worn-in cool that other bars try to imitate and never get right.
The Hideout Inn
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It looks like someone’s house, and it might actually have been someone’s house. Inside, you’ll find a tight-knit crowd of music lovers, artists, and people who still pay cover in cash—plus beer that’s cheaper than therapy. It’s the kind of place where everything feels like it still matters.
Kibbitznest Books, Brews & Blarney
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This is a bar disguised as a bookstore, or maybe a bookstore disguised as a bar. There’s no wi-fi, and laptops are discouraged, which means people here actually talk to each other. You can nurse a whiskey while reading a 1973 copy of Esquire, and nobody will blink.
The Library at Gilt Bar
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Down a candlelit staircase beneath Gilt Bar, this space feels like Gatsby’s secret reading room. The room has plush leather armchairs, shelves of books you’ll pretend to peruse, and a bar that serves actual grown-up drinks. It’s intimate without trying too hard.
The Office
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Located downstairs from The Aviary and behind an unmarked door, The Office is where bartenders go when they’re off duty. It's part speakeasy and part spirit library, with old leather chairs and vintage booze you’ve never heard of. You can skip the menu and let them surprise you—that’s half the fun.
Three Dots and a Dash
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This is a tiki bar, but not the cringey kind with plastic leis and sugar-bomb drinks. Here, rum cocktails come in skulls, pineapples, and sometimes fire, all made with real technique. The hidden entrance down an alley will impress those friends you convinced to come along.
Uptown Lounge
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This spot is not trendy, not new, and not interested in impressing you. It is a bar for locals, insomniacs, and night-shift workers looking to unwind with a stiff rum and Coke before a karaoke set. It’s also one of the only places in the neighborhood open until 4 a.m. without requiring an exorcism afterward.
6. The Whistler
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The Whistler blends live music, rotating DJs, gallery shows, and well-crafted cocktails in a dimly lit, wood-lined room. You can show up early for acoustic jazz or stay late for vinyl sets, and it never feels like a nightclub—just a beautifully chaotic creative salon. There’s even a small patio out back, perfect for catching your breath between songs.
