Downtown Chicago’s Best Spots to Drink

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A view through the windows at Bar Mar into downtown Chicago.
Toast to a bustling season in the Loop.
Garrett Sweet/Eater Chicago

There are plenty of great bars and restaurants for a delicious alcoholic beverage

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Toast to a bustling season in the Loop.
| Garrett Sweet/Eater Chicago

Despite its reputation among (some) Chicagoans as a playground for out-of-towners, the Loop is an important neighborhood for reasons beyond tourist revenue. It’s a place where workers, locals, and visitors converge, packed with stunning historic architecture and fine arts institutions that define Chicago to the rest of the country. For many newcomers, it’s the site of their first impression of the city — and its hospitality industry, a diverse and exciting arena that’s earned its world-class status.

That’s a lot of pressure for one neighborhood, so Eater Chicago is here to help locals and tourists navigate the scene and refuel from a day of downtown activities. Check out the lineup of top spots below — the list is focused on the Loop.

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This luxurious riverside seafood spot that bears the name of famed chef and activist José Andrés is a hit with Chicago’s happy hour crowd, who flock to the sun-drenched two-bar space for cocktails like the staple Salt Air Margarita topped with a salty foam cloud. There are also three types of sangria, a raw bar, and a stacked lineup of conservas.

A fancy island bar inside Bar Mar.
Bar Mar is a lively happy hour destination.
Garrett Sweet/Eater Chicago

Running a restaurant inside Willis Tower is no small feat, but James Beard Award-winning chef Jonathon Sawyer has proven up to the task with is work at Kindling, a collaboration with Fifty/50 Restaurant Group starring an opulent menu of fire-grilled dishes. Sawyer’s most-discussed dish is a luxe Italian beef made with meat sourced from a boutique farm, bread from 3D Baking, and giardiniera from local icon J.P. Graziano’s.

A bright bar area and tables inside Kindling.
Kindling was part of a $500 million renovation at Willis Tower.
Chris Peters/Eater Chicago

A quirky, quaint downtown favorite for more than half a century, Monk’s has evolved in parallel with the city of Chicago. Originally a dim watering hole in “the ass end of the Loop” (per owner Mike Shaker) with just a single draft line of Schlitz, Monk’s has improved with age — there are now nearly 200 craft beers on tap and by the bottle — and earned an ever-growing fanbase that followed the business after a move in 2015. Adherents also rave about the burgers and cozy European inn-style atmosphere.

The bar team at this swanky cocktail haven inside the Kimpton Gray Hotel designs its menu to riff on and reinterpret classic mid-century American drinks. Recent submissions from a “judiciary-inspired” lineup include the punny Burden of Proof (Sazerac rye, ancho reyes chile, crème de banane) and Overruled! (pineapple rum, baijiu, pineapple, apricot). The decor channels the romantic intimacy of a fancy library, inspiring some local couples to book it as a wedding venue.

Among regular bar-goers in the Loop, it’s rare to find a Chicagoan who doesn’t have a story related to the infamous Ceres Cafe. Founded in 1989 inside the Chicago Board of Trade Building, Ceres is — to put it mildly — a bar for serious drinkers, noted for its generous four-finger pours (mixers are, in essence, waved over the glass). A backdrop for local scandals (see: a certain former police superintendent) and innumerable gin-soaked evenings, the bar has earned a prominent place in the city’s hospitality lore.

Chicago’s mercurial weather patterns meet their match at Boleo, a South American rooftop lounge and restaurant with a retractable glass roof atop the Kimpton Gray Hotel. Designed to create the feeling of al fresco hospitality regardless of precipitation, it specializes in colorful, crowd-pleasing drinks like Passion Puma (Vida mezcal, jequitiba rosa, guava) and Two to Tango (Plantation rum, Giffard banana, Dolin Blanco, huna, melon). Balance out the booze with cevices, empanadas, and large plates like bone-in grilled pork chops.

A spacious bar area inside Boleo.
A glass roof fills Boleo’s space with sunlight.
Sarah Joyce/Eater Chicago

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Revival is a familiar player in Chicago’s food hall scene, and for those seeking afternoon cocktails, its all-day Revival Cafe-Bar is a compelling and low-lift contender. Out-of-town visitors might get a thrill out of the Windy City-themed menu of drinks like the Wrigley Building (Spanish brandy, Jamaican rum, amaro, orange marmalade) there are fun happy hour offerings like a build-your-own highball.

Snag a spot on the patio at this casual bar and restaurant inside the Marquette Building, a local landmark that dates back to 1895, and watch the world go by on Adams Street with a cocktail in hand. The Marq offers menus for breakfast, lunch, and dinner, as well as a kids menu for pint-sized patrons.

Though it debuted in 2023, this lively French bistro from the brothers behind Victor Bar manages to feel like a seamless extension of the historic architectural landmark it calls home. Tucked inside the ground floor of the 130-year-old Monadnock Building, it neatly translates the bistro genre’s upscale yet unpretentious atmosphere with elegant drinks like a summery melon sour (vodka, melon, aveze, lemon, egg white) and sumptuous bouillabaisse.

A cocktail with a foamy egg white cap and dried citrus round on a silver tray.
Bistro Monadnock is the first restaurant from the brothers behind Victor Bar and Love Street.
Barry Brecheisen/Eater Chicago

Sisters and co-owners Clodagh and Amy Lawless (whose brother, Billy, is also in the restaurant business) have pulled off a neat trick at the Dearborn, their lively bar and restaurant on the ground floor of Block 37 shops — they’ve earned the favor of both locals and tourists, groups that frequently diverge when it comes to city dining. A self-described American tavern, it’s a reliable standby for twists on classic cocktails and bountiful brunches.

A long, narrow bar area with high-top seating at the Dearborn.
The Dearborn brings a sophisticated dining to the Block 37 Shops.
Marc Much/Eater Chicago

An under-the-radar hit among downtown Chicago’s would-be songstresses and crooners, Brando’s has carved out a niche with karaoke, solid happy hour specials, and Roaring 20s-era decor. It attracts an eclectic crowd, so the people-watching is top-notch.

The former Plymouth rooftop has been rebranded from the same family behind Hollywood Grill and Griddle21. Ownership feels Mexican cuisine and beverages can bring some energy back into the space with drinks like sangria, margaritas, and palomas. Despite the new decor, the space remains a classic.

Barry Brecheisen/Eater Chicago

The Loop has a lot of stalwarts — not that there’s anything wrong with that — but the neighborhood is ripe for new ideas and fresh energy. Enter Industry Ales, a brewery and brewpub from a trio of hospitality veterans who attune their diverse assortment of beers to pair well with food. The menu attends to standbys like burgers and steak frites, but it’s worth exploring the fun and unexpected bar snacks. Think pizza samosas (creminis, caramelized onions, provolone), XO beef skewers, and albondigas with candied Fresno peppers.

A casual, bourbon-focused pub from the cousins and heirs to Loop neighbor the Exchequer, 2Twenty2 plays all the hits for folks who need to refuel after a hard day of shopping on the Mag Mile. The team features familiar drinks including boulevardiers, negronis, and Manhattans alongside burgers, sandwiches, and tavern-style pizzas. If food and drink isn’t enough entertainment, there are also games like giant Jenga and shuffleboard.

Arguably the best embodiment of truly old-school Chicago hospitality, Miller’s Pub is an institution that’s endured for nearly nine decades and the bustle shows no signs of stopping. A full-service restaurant stuffed with photos and memorabilia, it’s known for a great happy hour and Chicago-style broiler ribs.

A casual hang serving thin pizzas and barbecue ribs since 1982, Exchequer is particularly notable for those with a penchant for Chicago gangster lore. The building allegedly housed a speakeasy visited by Al Capone, who is said to have owned a brothel upstairs.

A legend in his own right, famed musician and octogenarian Buddy Guy still takes the stage at Buddy Guy’s Legends, his 35-year-old club near Printer’s Row. Regarded as one of the best spots for live blues and jazz in the country, the venue is a destination for music lovers and serves a menu of Cajun dishes and soul food.

The lobby bar inside the Pendry Hotel provides an excellent excuse to look around inside Chicago’s gorgeous Carbon and Carbide Building, a soaring Art Deco structure that dates back to 1929. It’s a comfortable perch to take in the design and sip cocktails or boozy tea.

A cozy lounge space and fireplace inside Bar Pendry.
The building that houses Bar Pendry was erected in 1929.
Barry Brecheisen/Eater Chicago

It’s hard to top the view from Cindy’s, the chic rooftop restaurant atop the Chicago Athletic Association hotel where Top Chef: Wisconsin contestant Kaleena Bliss works against a backdrop of Millennium Park and beyond, Lake Michigan. It’s a prime vantage point to settle in with a cocktail like Downtown Train (Botanist gin, Citadelle gin, heirloom alchermes liqueur, tart cherry) and admire the city from above.

A prominent go-to across from Millennium Park, the Gage, from Billy Lawless (whose sisters, Clodaugh and Amy, are also in the restaurant business) applies an upscale lens to the Irish pub with a menu ranging from familiar favorites like fish and chips and burgers to prime steaks, seafood towers, and wild mushroom ragout. That wide-ranging approach extends to a bar menu featuring spins on classics such as three varieties of spring-themed Old Fashioneds and a trio of creative highballs.

A long wooden bar lined with stools inside the Gage.
The Gage is a prominent longtime staple along Michigan Avenue.
Barry Brecheisen/Eater Chicago

Hotel guests and visitors at the palatial Chicago Athletic Association are spoiled for choice when it comes to dining and drinking options but Milk Room, its cocktail den, is singular in its devotion to hard-to-find spirits and vintage ingredients.

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This luxurious riverside seafood spot that bears the name of famed chef and activist José Andrés is a hit with Chicago’s happy hour crowd, who flock to the sun-drenched two-bar space for cocktails like the staple Salt Air Margarita topped with a salty foam cloud. There are also three types of sangria, a raw bar, and a stacked lineup of conservas.

A fancy island bar inside Bar Mar.
Bar Mar is a lively happy hour destination.
Garrett Sweet/Eater Chicago

Running a restaurant inside Willis Tower is no small feat, but James Beard Award-winning chef Jonathon Sawyer has proven up to the task with is work at Kindling, a collaboration with Fifty/50 Restaurant Group starring an opulent menu of fire-grilled dishes. Sawyer’s most-discussed dish is a luxe Italian beef made with meat sourced from a boutique farm, bread from 3D Baking, and giardiniera from local icon J.P. Graziano’s.

A bright bar area and tables inside Kindling.
Kindling was part of a $500 million renovation at Willis Tower.
Chris Peters/Eater Chicago

A quirky, quaint downtown favorite for more than half a century, Monk’s has evolved in parallel with the city of Chicago. Originally a dim watering hole in “the ass end of the Loop” (per owner Mike Shaker) with just a single draft line of Schlitz, Monk’s has improved with age — there are now nearly 200 craft beers on tap and by the bottle — and earned an ever-growing fanbase that followed the business after a move in 2015. Adherents also rave about the burgers and cozy European inn-style atmosphere.

The bar team at this swanky cocktail haven inside the Kimpton Gray Hotel designs its menu to riff on and reinterpret classic mid-century American drinks. Recent submissions from a “judiciary-inspired” lineup include the punny Burden of Proof (Sazerac rye, ancho reyes chile, crème de banane) and Overruled! (pineapple rum, baijiu, pineapple, apricot). The decor channels the romantic intimacy of a fancy library, inspiring some local couples to book it as a wedding venue.

Among regular bar-goers in the Loop, it’s rare to find a Chicagoan who doesn’t have a story related to the infamous Ceres Cafe. Founded in 1989 inside the Chicago Board of Trade Building, Ceres is — to put it mildly — a bar for serious drinkers, noted for its generous four-finger pours (mixers are, in essence, waved over the glass). A backdrop for local scandals (see: a certain former police superintendent) and innumerable gin-soaked evenings, the bar has earned a prominent place in the city’s hospitality lore.

Chicago’s mercurial weather patterns meet their match at Boleo, a South American rooftop lounge and restaurant with a retractable glass roof atop the Kimpton Gray Hotel. Designed to create the feeling of al fresco hospitality regardless of precipitation, it specializes in colorful, crowd-pleasing drinks like Passion Puma (Vida mezcal, jequitiba rosa, guava) and Two to Tango (Plantation rum, Giffard banana, Dolin Blanco, huna, melon). Balance out the booze with cevices, empanadas, and large plates like bone-in grilled pork chops.

A spacious bar area inside Boleo.
A glass roof fills Boleo’s space with sunlight.
Sarah Joyce/Eater Chicago

Revival is a familiar player in Chicago’s food hall scene, and for those seeking afternoon cocktails, its all-day Revival Cafe-Bar is a compelling and low-lift contender. Out-of-town visitors might get a thrill out of the Windy City-themed menu of drinks like the Wrigley Building (Spanish brandy, Jamaican rum, amaro, orange marmalade) there are fun happy hour offerings like a build-your-own highball.

Snag a spot on the patio at this casual bar and restaurant inside the Marquette Building, a local landmark that dates back to 1895, and watch the world go by on Adams Street with a cocktail in hand. The Marq offers menus for breakfast, lunch, and dinner, as well as a kids menu for pint-sized patrons.

Though it debuted in 2023, this lively French bistro from the brothers behind Victor Bar manages to feel like a seamless extension of the historic architectural landmark it calls home. Tucked inside the ground floor of the 130-year-old Monadnock Building, it neatly translates the bistro genre’s upscale yet unpretentious atmosphere with elegant drinks like a summery melon sour (vodka, melon, aveze, lemon, egg white) and sumptuous bouillabaisse.

A cocktail with a foamy egg white cap and dried citrus round on a silver tray.
Bistro Monadnock is the first restaurant from the brothers behind Victor Bar and Love Street.
Barry Brecheisen/Eater Chicago

Sisters and co-owners Clodagh and Amy Lawless (whose brother, Billy, is also in the restaurant business) have pulled off a neat trick at the Dearborn, their lively bar and restaurant on the ground floor of Block 37 shops — they’ve earned the favor of both locals and tourists, groups that frequently diverge when it comes to city dining. A self-described American tavern, it’s a reliable standby for twists on classic cocktails and bountiful brunches.

A long, narrow bar area with high-top seating at the Dearborn.
The Dearborn brings a sophisticated dining to the Block 37 Shops.
Marc Much/Eater Chicago

An under-the-radar hit among downtown Chicago’s would-be songstresses and crooners, Brando’s has carved out a niche with karaoke, solid happy hour specials, and Roaring 20s-era decor. It attracts an eclectic crowd, so the people-watching is top-notch.

The former Plymouth rooftop has been rebranded from the same family behind Hollywood Grill and Griddle21. Ownership feels Mexican cuisine and beverages can bring some energy back into the space with drinks like sangria, margaritas, and palomas. Despite the new decor, the space remains a classic.

Barry Brecheisen/Eater Chicago

The Loop has a lot of stalwarts — not that there’s anything wrong with that — but the neighborhood is ripe for new ideas and fresh energy. Enter Industry Ales, a brewery and brewpub from a trio of hospitality veterans who attune their diverse assortment of beers to pair well with food. The menu attends to standbys like burgers and steak frites, but it’s worth exploring the fun and unexpected bar snacks. Think pizza samosas (creminis, caramelized onions, provolone), XO beef skewers, and albondigas with candied Fresno peppers.

A casual, bourbon-focused pub from the cousins and heirs to Loop neighbor the Exchequer, 2Twenty2 plays all the hits for folks who need to refuel after a hard day of shopping on the Mag Mile. The team features familiar drinks including boulevardiers, negronis, and Manhattans alongside burgers, sandwiches, and tavern-style pizzas. If food and drink isn’t enough entertainment, there are also games like giant Jenga and shuffleboard.

Arguably the best embodiment of truly old-school Chicago hospitality, Miller’s Pub is an institution that’s endured for nearly nine decades and the bustle shows no signs of stopping. A full-service restaurant stuffed with photos and memorabilia, it’s known for a great happy hour and Chicago-style broiler ribs.

A casual hang serving thin pizzas and barbecue ribs since 1982, Exchequer is particularly notable for those with a penchant for Chicago gangster lore. The building allegedly housed a speakeasy visited by Al Capone, who is said to have owned a brothel upstairs.

A legend in his own right, famed musician and octogenarian Buddy Guy still takes the stage at Buddy Guy’s Legends, his 35-year-old club near Printer’s Row. Regarded as one of the best spots for live blues and jazz in the country, the venue is a destination for music lovers and serves a menu of Cajun dishes and soul food.

The lobby bar inside the Pendry Hotel provides an excellent excuse to look around inside Chicago’s gorgeous Carbon and Carbide Building, a soaring Art Deco structure that dates back to 1929. It’s a comfortable perch to take in the design and sip cocktails or boozy tea.

A cozy lounge space and fireplace inside Bar Pendry.
The building that houses Bar Pendry was erected in 1929.
Barry Brecheisen/Eater Chicago

It’s hard to top the view from Cindy’s, the chic rooftop restaurant atop the Chicago Athletic Association hotel where Top Chef: Wisconsin contestant Kaleena Bliss works against a backdrop of Millennium Park and beyond, Lake Michigan. It’s a prime vantage point to settle in with a cocktail like Downtown Train (Botanist gin, Citadelle gin, heirloom alchermes liqueur, tart cherry) and admire the city from above.

A prominent go-to across from Millennium Park, the Gage, from Billy Lawless (whose sisters, Clodaugh and Amy, are also in the restaurant business) applies an upscale lens to the Irish pub with a menu ranging from familiar favorites like fish and chips and burgers to prime steaks, seafood towers, and wild mushroom ragout. That wide-ranging approach extends to a bar menu featuring spins on classics such as three varieties of spring-themed Old Fashioneds and a trio of creative highballs.

A long wooden bar lined with stools inside the Gage.
The Gage is a prominent longtime staple along Michigan Avenue.
Barry Brecheisen/Eater Chicago

Hotel guests and visitors at the palatial Chicago Athletic Association are spoiled for choice when it comes to dining and drinking options but Milk Room, its cocktail den, is singular in its devotion to hard-to-find spirits and vintage ingredients.

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