In Chicago, summer isn’t marked by Memorial Day or the end of school, but rather the emergence of rooftop bars from their seasonal slumber. After an extended winter, and a reliably fickle spring, rooftop season signals that warm weather has arrived—and so have the thirsty hordes of sky-high imbibers. Around here, in the birthplace of the skyscraper, where architecture and craft co*cktails are equally beloved, the almighty rooftop bar is a veritable rite of summer passage. And from swanky terraces to boozy adult playgrounds, there’s a rooftop bar out there for everyone of age. So gather your friends and hit up these 15 rooftop bars for some of the best views in Chicago—served with a side of booze.
West Loop
The closest you’ll likely come to replicating a fresh breeze off the Amalfi Coast, Tetto is the sun-soaked rooftop deck from the owners of Tabú downstairs. Up here, the massive 8,000-square-foot space offers sweeping skyline views from its West Loop perch, along with eclectic art installations, twinkling lights, and chic lounge chairs aplenty. Newly open for the summer season, Tetto’s menu doubles down on Italian with a food menu curated by Professor Pizza (think: salumi boards, meatballs, and of course, pizza) and a full slate of easy-breezy summer sippers, like Negronis and requisite Aperol Spritzes.
Gold Coast
Posh poolside sipping isn’t exactly easy to come by in Chicago, a city known more for its blustery weather than any abundance of sunshine. But this swanky rooftop complex, formerly known as Devereaux, atop the Viceroy Chicago, aims to nip that perception right in the bud. Eighteen floors up, it’s one of the tallest open-air venues in the city, flaunting its seasonal prowess by way of a sparkling blue pool surrounded by contemporary lounge furniture, lush plants, and unbeatable lakefront views. And we haven’t even gotten to the bounty of Southeast Asian small plates and smart co*cktails streaming out of the bustling kitchen and bar—pair Nori Fries and Sweet Corn Tempura with a Yuzu Spritz or the fluffy Red Panda, with whiskey, turmeric, ginger, lemon, pineapple, and egg white.
Château Carbide
Loop
If there’s a neighborhood in Chicago that serves as the epicenter of rooftop swilling, it’s the Loop. This soaring hub, after all, is the birthplace of the skyscraper, and it still reigns as the nexus of the city’s most staggering architecture. Despite the omnipresence of its rooftop bars, there are really never enough. Case in point: Château Carbide, a relative newcomer in a timeworn space. Nestled on the 24th floor of the historic Carbide & Carbon Building, an Art Deco beaut built in 1929 and accessorized with gold terra cotta and bronze trim, the bar is the crown jewel of the Pendry Chicago hotel. It boasts both a garden-clad outdoor terrace and an opulent indoor motif inspired by the Cote D’Azur—on weekend evenings, DJs curate playlists heavy on French house music. To drink, look for lots of rosé, Champagne, absinthe, and elegant co*cktails, like the aptly dubbed Summer Day, with vodka, elderflower, cucumber, sparkling Sicilian lemonade, and basil shrub.
Bar Avec
River North
One of the newest members of the One Off Hospitality family isn’t messing around when it comes to sweeping birds-eye views and magnificent spreads—but we wouldn’t expect anything less from the folks behind beloved Mediterranean standby Avec. Brought to life with lush potted plants, hanging pendant lanterns, smooth wooden patio furnishings, and overhead heaters for those nippy early spring nights, this wine-focused, 8th-floor perch gazes east over the Magnificent Mile. Up for a date night challenge? See who can correctly identify the most surrounding skyscrapers by name while snacking on Bacon-Wrapped Medjool Dates and a few refreshing aperitivos.
Boleo
Loop
In the heart of the Financial District, the circa-1894 former New York Life Insurance Building, also experienced a glow-up. Thanks to Boleo, the lush rooftop bar atop the Kimpton Gray Hotel that now fills the building, the former insurance mecca has a new forte—Peruvian small plates and pisco co*cktails. The all-season rooftop features a retractable glass roof, Latin-leaning DJ sets, and vibrant drinks designed to transport guests to South America by way of a glass coupe. Peruvian classics, like pitch-perfect Pisco Sours and ginger beer-splashed Chilcanos, share bar space with quenching originals like the tropical Capybara, a juicy blend of cachacas and mango with lime and starfruit. Pair it with a smattering of Peruvian snacks, like ceviche, kale empanadas, and crispy Yucca Fries.
The Up Room
Wicker Park
Thanks to a recent makeover, this towering Wicker North haunt atop The Robey’s iconic flatiron building sports an interior aesthetic just as sexy as its exterior panorama. Settle into the plush mid-century modern lounge seating and revel in the atmosphere as you dive into seasonal co*cktails (don’t miss the Oaxacan on Broken Glass, a mix of mezcal, chile, lime, and Hellfire Bitters) and killer charcuterie boards. This intimate and approachable space, set to a soothing soundtrack, makes for an ideal venue for romantic post-dinner nightcaps and first dates alike. A few floors down, Cabana Club’s rooftop oasis in the same building re-emerged for the season as a Mediterranean-inspired semi-private day club. Located on the sixth floor, people know this comparatively pint-sized patio for its 180-degree vistas overlooking the L tracks, as well as its chic wading pool. Cabana Club 2024 offers ticketed day passes and fresh plates like grilled shrimp skewers, garlic hummus, and pork kofta.
Cabra
West Loop
Stephanie Izard strikes again with this sky-high haven, found atop the hipster-approved Hoxton Hotel. The menu pays homage to the lauded chef’s memories of traveling around Peru, as emphasized by inspired nibbles like Goat Empanadas and Crab Causa. Pair them with drinks that are just as wanderlust-inducing, such as the Return of Saturn, with gin, passion fruit, falernum, and amaretto, or the refreshing Sweater Weather, a frozen medley of vodka, coffee liqueur, banana, and spiced pear.
The Rooftop at Nobu Hotel Chicago
West Loop
Expect the same serene, chic aesthetic here that permeates the entirety of this buzzy West Loop hotel, which debuted during the pandemic with a dynamite team of backers (Nobu Matsuhisa, Robert DeNiro, and Meir Teper, to name a few). Kick things off with a round of sushi, of course, then move on to tempting bites like Black Cod Butter Lettuce cups or Lobster Tempura, alongside Asian-inspired co*cktails like Lychee-Elderflower Martinis and the Nobu Old Fashioned, a bracing blend of bourbon whiskey, orange liqueur, and Angostura Bitters over hand-carved ice. New this year is a weekend brunch menu, featuring the likes of Miso-Braised Short Rib Benedict, Karaage Chicken Thighs & Waffles, and Milk Bread Cinnamon Rolls.
Cindy’s
Loop
Make a beeline to this inviting rooftop for some of the most legendary views of the city—ones that capture postcard-ready panoramas of Millennium Park, Cloud Gate, Navy Pier, and miles upon miles of Lake Michigan’s shoreline. With views and decor this astounding, the bar team could easily serve bottom-shelf booze and make a killing, but the drinks somehow manage to match the vista. Breathe it all in with a side of the talented team’s boozy handiwork, namely the Trouble Will Find Me, a summer-colored blend of tequila, mezcal, sherry, watermelon, lime, agave, and yuzu soda, or the Peachy Keen, a fruity mashup of Japanese whisky, Scotch, elote liqueur, peach, and lemon.
LondonHouse Rooftop
Loop
Chicago’s only tri-level rooftop extends in glorious fashion from the 21st to 23rd floors of the LondonHouse hotel’s historic Beaux Arts tower. The 23rd floor cupola is only available for private reservations, but it’s nevertheless hard to find a better spot for mingling with Chicago’s upper crust over General Tso’s Bao Buns and Louisiana Crab Dip paired with requisite Espresso Martinis, Guava Margaritas, and large format bottles of Armand de Brignac. Plus, its unique perch at the nexus of Michigan Avenue and Wacker Drive affords unparalleled views of the Chicago River.
Gene’s Sausage Shop
Lincoln Square
Head north to Lincoln Square to find this absolute gem of a wine bar and biergarten, stashed, curiously enough, on top of an unassuming family-owned sausage shop and deli. Snag a picnic table and go all in on house-cured meats alongside heartier dishes like Schnitzel and Golabki amid the cheery greenery and Old World stylings. To drink, you’re looking at a strong but streamlined list of imported and domestic beers plus easy-drinking reds and whites by the glass. What’s not to like?
Lonesome Rose
Logan Square
For laidback open-air boozing in one of the city’s hippest ‘hoods, head to this cheerful Land and Sea emporium festooned with Tex-Mex-inspired decor and enough tequila to keep you fully entertained. Bask in the sun while sampling through an extensive array of tacos, burritos, and bowls—all on-point chaperones for a few extra rounds of palomas and margaritas. Later, let those hot summer days lead you straight into dessert: “Chaco-Tacos” with horchata ice cream are calling. Need a break from the sun? Head downstairs to Lonesome Rose’s subterranean speakeasy, Golden Teardrops.
Streeterville
No rooftop roundup would be complete without the inclusion of this 56,000-square-foot destination, which debuted as the largest rooftop venue in America back in 2019. Teetering atop the third floor of Navy Pier’s Festival Hall, the spacious hangout offers plenty of room for mingling, plus grade-A views of the lake and an aptly themed bill of coastal bites like Beer-Battered Fish Sliders and Corn Succotash, alongside summery sippers like Gimme S’more, a drinkable dessert with bourbon, Bird Dog S’mores Whiskey, chocolate bitters, orange bitters, toasted marshmallow, and graham cracker rim.
The J. Parker
Lincoln Park
For stellar, unobstructed views of the lake and Lincoln Park’s sunny expanse, visit this neighborhood favorite, found atop the Hotel Lincoln. With a retractable roof and an excellent burger (not to mention “Chicago Dog” tacos), this perennially cool option—named after one of Lincoln's bodyguards, no less—holds court as a pillar of Chicago’s year-round drinking scene.
Utopian Tailgate
Old Town
This fun-filled, 10,000-square-foot playpen atop world-famous comedy hub Second City remains one of the city’s most popular outdoor options. Ablaze in vibrant colors and packed with group-friendly games like giant Connect Four and cornhole, it radiates with the same kind of joy that fuels the rest of the landmark building that gave some of the world’s most lauded comedians their start. Swing by for some tailgate-themed eats and tropical drinks while relaxing in style courtesy of neon-hued Adirondack chairs.
Matt Kirouacis a contributor for Thrillist.
