21 Chicago Rooftop Bars with Breathtaking Views

The newest member of the One Off family isn’t messing around when it comes to epic views and even more epic 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 wood patio furnishings, and overhead heaters for those nippy early spring nights, this wine-focused eighth-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 over 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 Hotel’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—the Oaxacan on Broken Glass (mezcal, Ancho Reyes, lime, Ango, Hellfire Bitters) can’t miss— and a killer charcuterie board. Intimate yet approachable and set to a soothing soundtrack, it’s the ideal venue for a romantic post-dinner nightcap and first date alike.
How to book: Stop by for first come, first served seating.

A tribute to Time Out’s founder Tony Elliott’s legacy, this cozy rooftop hideaway is the proverbial cherry on top of the publication’s buzzy West Loop food hall. Vintage magazine covers grace the walls while dark wood beams provide year-round shelter for bar-goers bending an elbow along the stately bar. Saddle up inside for craft beer, wine, and an exciting roster of cocktails or post up outside on the terrace for some vitamin D with a side of downtown views.
How to book: Stop by for first come, first served seating.

A retractable glass roof crowns this all-weather sky-high lounge, which in recent years swapped its distinctively clubby vibe for a more sophisticated aesthetic complete with broad leather booths, low-slung sofas, and modern fixtures throughout. Tasty shareables like cheese boards, flatbreads, sushi platters, and Parmesan fries spice things up while the bar program revolves around creative and classic cocktails plus bottle service and large format punches fit for a small, thirsty army.

Peer out over the Mag Mile from your seat atop this 10,000-square-foot fourth floor oasis in the Godfrey Hotel Chicago. 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.
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 swank rooftop complex atop the Viceroy Chicago aims to nip that perception right in the bud. At 18 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—Maine Lobster Sliders, anyone?
How to book: Reserve via Tock.

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?
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 two house favorites: Anticuchos (marinated meats grilled over flames) and Ceviches (a nod to Izard’s time in Lima). Pair them with drinks that are just as wanderlust-inducing, such as the Golden Hour, a bubbly highball stocked with Glenmorangie Scotch, mango vin, grapefruit, lime, and ginger ale, or the Frozen Pisco Fever, a vibrant and aromatic mix of pisco, vodka, guava, lime, and pineapple.

Expect the same serene-chic aesthetic here that permeates the interior of this hotly anticipated West Loop addition, which debuted during the pandemic with a dynamite team of backers (think: chef 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 Miso or Rock Shrimp Tempura alongside Asian-inspired drams like Lychee-elderflower Martinis and the Nobu Sidecar, a sultry concoction spiked with Japanese whisky and tart yuzu.

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 Paloma Colorada, a summer-ready blend of Avion Blanco tequila, Rhine Hall Fernet Lola, blood orange, lime, and saline, or the Prickly Rose, a floral ambrosia of Hendrick’s Gin, Apologue Persimmon Liqueur, prickly pear, lemon, and a dash of Prosecco.

Swing up to this River North rooftop for South American vibes and Peruvian plates that draw on a variety of culinary traditions from Japanese and Chinese to Spanish and Pan-African. Try the Cebiche Clasico, with leche de tigre, sweet potatoes, and choclo (large Peruvian corn kernels)—the ultimate accompaniment to all those Pisco Sours you’ll be downing. And don’t miss the Nigiri Pobre, a layering of rice, wagyu, and fried quail egg that serves as one of the city’s best dishes.

Gibson’s fans were amped about this 2017 opening, an upscale Italian approach that employs the same quality and attention to detail as its sister steakhouses. And then, of course, there are the Chicago River views, made possible by two sprawling waterfront dining and drinking areas. Stick to the classics here with some of the team’s top tipples—we’re talking Manhattans and Old Fashioneds—and complement those sophisticated sippers with an order of seven-year-aged Acquerello Risotto dotted with scallops and baby leeks.

The digs are just as enticing as the menu inside this Loop-situated sanctuary, where guests are greeted by a locally painted mural and several fire pits ready to warm up even the chilliest spring eve. Take advantage of them during special events like Movie Night Thursdays, your chance to check out classic films alongside a cinema-inspired cocktail. When hunger strikes, opt for any of the menu’s crowd-pleasing plates, from Campari Glazed Pork Spareribs to a House Burger decked out with shortrib jam and American cheese.
How to book: Reserve via Tock.

One of the most buzzworthy openings of recent years is this internationally inspired stunner on the sixth floor of the Peninsula Chicago. The next time you’re looking to duck tourists, pop into this globally curated hotspot for dishes like Beef Short Rib Poutine and Daikon Frites paired with craft cocktails and a live DJ.
How to book: Reserve via Tock.

Keeping things cool on the 26th floor of the Virgin Hotel, Cerise’s luxe flagship terrace wraps around a full three sides of the landmark building. With rotating DJ sets on Fridays and Saturdays, this casual-chic space brings a slice of LA to the Loop, aided by tasty fixes like Steak Frites, Olive Oil Poached
Shrimp Cocktail, and zesty Love Potion cocktails (Bombay Sapphire, cranberry, anise liqueur, tonic).

Proudly calling itself the “Trainwreck Rooftop Deck,” this South Loop rock club’s upstairs expanse offers a delightful diversion from downtown’s upmarket-leaning al fresco scene. The anything-goes boozy playground features eight flat screen TVs, a pool table, a Pop-A-Shot machine, and picnic tables for snacking on a host of pub grub must-tries.
How to book: Stop by for first come, first served seating.

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 nevertheless, it’s hard to find a better spot for mingling with Chicago’s upper crust over Empanadas and Louisiana Crab Dip paired with large format bottles of Armand de Brignac.
How to book: Reserve via Tock.

For laidback open-air boozing in one of the city’s hippest ‘hoods, head to this cheerful Land & Sea emporium festooned with Tex-Mex-inspired décor 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 Margs. Later, let those hot summer days lead you straight into dessert—horchata soft serve is calling.

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. Teetered atop the third floor of Navy Pier’s Festival Hall, the spacious hangout offers plenty of room for social distancing plus A-grade views of the lake and an aptly themed bill of coastal bites like Shrimp Tempura Maki and Faroe Island Salmon alongside uplifting sippers like the Melondramatic (Casamigos Blanco tequila, Twisted Alchemy watermelon juice, lime, agave).

For stellar, unobstructed views of the lake and Lincoln Park’s sunny expanse, visit this neighborhood favorite, found within the Hotel Lincoln. With a retractable roof and an excellent burger (not to mention Truffle Fries and Crispy Brussels Sprouts), 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 where some of the world’s most lauded comedians got their start. Swing by for some tailgate-themed eats and tropical bevvies while relaxin’ in style via neon-hued Adirondack chairs.