15 Chicago Rooftop Bars with Breathtaking Views

In the heart of the Financial District, the circa-1894 former New York Life Insurance Building, also experienced a glow-up recently. 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 cocktails. 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 daiquiri-esque 15th Parallel, a potent blend of rum, pisco, Makrut lime, clove, grapefruit, and honey. Pair it with a smattering of Peruvian snacks, like ceviche, Tuna Tiradito, and Chicharon Sliders.
How to book: Reserve via OpenTable.

The newest member 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.
How to book: Reserve via Tock.

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 cocktails (don’t miss the Oaxacan on Broken Glass, a mix of mezcal, Ancho Reyes, lime, Angostura Bitters, 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 will open for the season on Cinco de Mayo until Labor Day. Located on the 6th 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 2023 sports a drink menu heavy on summer-inspired quaffs, like Spiked Sweet Tea, Pisco Punch, and a new frozen iteration of The Up Room’s Oaxacan on Broken Glass. Meanwhile a new food menu from chef Michael Eliott draws inspiration from Mexican and barbecue cuisines, resulting in equally summery flavors like Barbecued Pork Tacos and Chipotle Chicken Quesadillas.
How to book: Stop by for first come, first served seating.

Peer out over the Mag Mile from your seat atop this 8,500-square-foot fourth floor oasis in the Godfrey Hotel Chicago—one of the largest in town. Armed with choice cocktails, a substantial New American menu, and indoor and outdoor options aplenty—not to mention fireplaces, fountains, a retractable roof, and seasonal draws like igloos strung with twinkling fairy lights—the thought of blissfully wasting away a Sunday afternoon up here is an ever-present temptation. There’s an exceptionally good happy hour here. Discounted drinks include cocktail flights, and small plates like Wagyu Beef Sliders and assorted macarons, are half off on Tuesday through Friday from 3 to 6 pm.
How to book: Reserve via Tock.

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 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 and unbeatable lakefront views. And we haven’t even gotten to the bounty of cheffy small plates and smart cocktails streaming out of the bustling kitchen and bar—Pretzel-Dusted Calamari, anyone? Devereaux’s pool opens for the season on April 27.
How to book: Reserve via Resy.

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? Gene’s rooftop opens for the season on Memorial Day weekend.
How to book: Stop by for first come, first served seating.

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 Passion of Peru, a sweet-and-smoky mashup of mezcal, passion fruit, honey, and lemon, or the refreshing Cabra Cool-Aid, with tequila, cherry liqueur, lime, and egg white.
How to book: Reserve via OpenTable.

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 cocktails like Lychee-Elderflower Martinis and the Japanese Old Fashioned, a bracing blend of Japanese whiskey, Luxardo cherry, Demerara, and Angostura Bitters over hand-carved ice.
How to book: Reserve via OpenTable.

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. Breathe it all in with a side of the talented team’s boozy handiwork, namely the Deep Purple, a summer-colored blend of vodkas, sherry, blue matcha syrup and lemon, or the Bonfire Party, a fragrant brew of Japanese whisky, Cachaça, cranberry, orange, and lemon.
How to book: Reserve via Resy.

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 Grilled Octopus Salad and Louisiana Crab Dip paired with requisite Espresso Martinis 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.
How to book: Reserve via Tock.

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: Horchata soft-serve is calling. Need a break from the sun? Head downstairs to Lonesome Rose’s subterranean speakeasy, Golden Teardrops.
How to book: Reserve via Resy.

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 Fish and Chips and Faroe Island Salmon alongside uplifting sippers like the Teenage Dreamsicle (Grey Goose Watermelon Basil, bergamot liqueur, blood orange, lime, simple syrup, orange bitters).
How to book: Reserve via OpenTable.

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-Style Corn Dogs”), 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.
How to book: Stop by for first come, first served seating.

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.
How to book: Reserve via Resy.