It’s a story as old as the city itself: Back when railroads were all the rage-i.e., the mid- to late-19th century-Chicago, fresh off 1871’s devastating fire, rose to prominence as America’s number one transit hub. Thanks to competing lines, it was impossible for an East Coaster to make their way west without changing trains, and vice-versa. And as a centrally located industrial powerhouse with an already thriving freight presence, Chicago was a natural place for passengers to transfer from one line to the other. There was a catch, however: Schedules didn’t often align perfectly, forcing many travelers to spend their overnight layovers exploring the Windy City. And Chicago’s rapidly expanding assortment of hotels were more than happy to meet their needs.

Of course, with those hotels came restaurants and, more importantly, bars. These drinking emporiums mirrored the opulence of their surroundings, designed to woo out-of-towners while also catering to the local moneyed classes. Today, despite both Prohibition’s and the aviation boom’s best efforts, Chicago’s hotel bar scene is still one of the country’s very finest, with options ranging from laid-back lounges with a view to age-old gems with Gilded Age-style flair. Here are the best of the best.

Broken Shaker

River North
Stashed away on the first floor of the always-bumping Freehand Chicago, iconic Broken Shaker does things a little bit differently. The space-dimly lit, cavernous, and cloaked in quirky nautical artwork-evokes a chilled out ‘70s vibe while a rotating cast of top-notch DJs spin vinyl for travelers and locals mingling on plush couches. And then, of course, there are drinks: thoughtful combos that skillfully play on classics like the paloma-esque So Fres$h & So Clean (Tromba Blanco tequila, Joseph Cartron Pamplemousse Rose, agave, lime, and acid solution) and the breakfast-ready Noah’s Old Fashioned (Reese’s Puffs cereal-infused Smooth Ambler bourbon, Angostura bitters, orange bitters, demerara). Hungry? Why wait-the kitchen has your back with satisfying bar bites like tacos, fried chicken sandwiches, elote, burrata with heirloom tomatoes, and mini churros.

IO Godfrey Rooftop Lounge

River North
Equipped with a clever retractable roof for year-round vibing, this River North fixture stands tall as the city’s largest rooftop bar. To complement its solid beverage program (see: Scarlet Haze, a delectable mix of Del Maguey Vida Mezcal, Cointreau, sour cherry, and black sea salt) and equally enticing pan-Asian cuisine, the bar hosts a never-ending lineup of fun-in-the-sun (or -snow) activities and events like an immersive haunted experience for Halloween and heated igloos come winter.

ROOF on theWit

Loop
This visually stunning 7,000-square-foot respite soars 27 stories above the earth. But it’s not just size that matters here. There’s also textured walls studded with artfully arranged flatscreens, verdant greenery, retractable walls, a gorgeous Deco-inspired back bar, and a host of refreshing cocktails and tasty shareables. All that plus bottle service and plenty of room for raucous DJ- and live music-fueled dance parties-what’s not to like?

Cindy’s Rooftop

Loop
The literal crown jewel of the recently renovated Chicago Athletic Association not only offers some of the best views of Millennium Park, it also shakes up some of the area’s finest cocktails for both indoor and outdoor consumption. The multi-page menu is a treat in itself, listing cheekily titled tipples like Raspberry Beret (Rittenhouse rye, Lustau oloroso sherry, raspberry, hibiscus, lemon) and Fernet About It (Beefeater gin, Fernet, lemon, strawberry ginger rosemary syrup, soda) alongside colorful little illustrations. As for food, brunch is big business in these parts, when hearty best-sellers like chorizo-laden chilaquiles, rich biscuits and gravy, and chicken and waffles take center stage.

The Lobby Bar at Lockwood 

Loop
Welcome to one of Chicago’s most ornate bars, where cathedral-like frescoed ceilings and towering marble columns surround a sparkling little bar stocked with unbeatable classics and seasonal twists (don’t sleep on the dangerously smooth 187 Whisky Sazerac). If you can’t make it to church on Sunday, it turns out the stately Palmer House Hotel is a perfectly acceptable alternative.

Milk Room

Loop
Over the years, beloved restaurant and design firm Land and Sea Dept. has left their mark on Chicago in many different ways-but no other concept quite compares to this diminutive cocktail den hidden within the Chicago Athletic Association’s second floor. Here, those lucky enough to have scored a seat (there are only eight of them) will find a treasure trove of rare and vintage spirits served on their own or stirred into exquisitely executed cocktails by the extremely knowledgeable staff. It’s no wonder the handsome outfit bears so many accolades, from local best bar nods to national rankings by Esquire and this year’s World’s 50 Best Bars.

Alma

Wrigleyville
If you thought Wrigleyville was all frat boys and sports bars, you wouldn’t exactly be wrong. But this sprawling lounge inside the Zachary Hotel is the polished exception to the norm-while still paying homage to its ballplayer roots. Fully revamped in June, 2023, it’s already proven itself a quality hangout, providing Northsiders with a wall of windows facing the Friendly Confines, plush mid-century modern decor, a glowing brick fireplace, historic photos, and a tastefully placed DJ booth primed for weekly vinyl nights. And to drink? Expect original concoctions brimming with proprietary booze like an Old Fashioned with Hotel Zachary Sherry Cask Jeppson’s bourbon and a house bitters blend, plus mini-flights for the cocktail-curious, frozen drinks, and a coveted Suntory Highball Machine (aka Japanese whisky sodas on tap).

Clever Coyote

Wicker Park
This new-like brand new-second-floor hangout inside The Robey’s 1929 landmarked building has hit the ground running with a neon-lit ‘90s throwback theme imbued with more Millennial nostalgia than an Alanis Morisette cover band. But don’t worry, you won’t find any Pop-Tarts and Snackwell cookies around here. Instead, the cocktail menu leans into tropical flavors, featuring kitschy headliners like the activated charcoal-spiked and agave-driven Black Hole Sun and Sucker Punch, a clarified gin milk punch topped off with a Spice Girls-endorsed lollipop.

Lazy Bird

Fulton Market
A charming mid-century aesthetic, deep circular booths, long marble bar, and 52 different cocktails converge to make this Fulton Market hideaway inside the interminably hip Hoxton Hotel one of the best in the business. Come for a laid-back evening sip before snagging a table upstairs at Cabra, or stop by for a couple of late-night libations accompanied by live music and a surprisingly clubby atmosphere on the weekend.

Bar Pendry

Loop
Posh cocktails and an eye-catching interior design beckon the swanky set into this operation inside the Pendry’s stunningly refurbished 1929 Art Deco Carbide & Carbon building. Select small bites play a supporting role to a perfectly balanced cast of cocktails where contemporary takes like the Crimson and Carbide (mezcal, lemon, beets, ghost pepper agave) square off with expertly made classics. And while the drinks are top notch, Bar Pendry really pulls with its library-meets-date night vibes, sporting a double-sided fireplace, butter-soft leather couches, and rich wood paneling.

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Meredith Heil is the Editorial Director of Thrillist Travel. Follow along with @mereditto.

Jay Gentile is a Thrillist contributor. Follow him:@innerviewmag.