The Wicker Park hotel the Robey has multiple options for a good time. Cabana Club, a rooftop bar on the building’s sixth floor, features a pool, two bars (serving frozen drinks), and unobstructed 360-degree views. For those seeking a more intimate setting, saunter over to the Up Room, the midcentury modern lounge on the 13th floor, to enjoy creative craft cocktails and dazzling sights.

Although it’s not near the lake, Homestead on the Roof is green oasis above a bustling Chicago neighborhood. Sample dishes made from seasonal ingredients, plus standout desserts and drinks. Fun fact: Some of the restaurant’s produce comes directly from its rooftop garden.

Prime views and indulgent luxuries are aplenty at the city’s first Nobu Hotel. The ritzy chain co-owned by Robert De Niro pulls out all the stops to impress, and on the rooftop, guests are in for an especially extravagant experience. Celebrity chef Nobu Matsuhisa’s Japanese-Peruvian menu features fresh sushi and hot dishes, such as miso black cod in butter lettuce, to go with the spectacular sights.

When the chic London-based lifestyle hotel the Hoxton touched down in Chicago in 2019, the company decided to partner with local hitmaker Stephanie Izard of Girl & the Goat fame. Cabra, which claims the Hoxton’s rooftop terrace, is dedicated to Peruvian cuisine and affords awesome views of the West Loop’s cityscape.

One of Chicago's most picturesque dining experiences is at this Michelin-starred spot next to a pond in Lincoln Park. The farm-to-table restaurant feels like taking a trip to the country while downtown skyscrapers rise in the distance.

Head to the rooftop above the Second City complex and discover a sprawling adult playground full of colorful furniture, picnic tables, lush plants, lawn games, tire swings, and more. The views only add to the fun while the menu features tailgate-themed foods like sliders, pizzas, and nachos, plus large-format cocktails and house shots. Sports fans will appreciate that there are numerous TVs showing the games throughout the space.

This rooftop draw atop Hotel Lincoln gives bird’s-eye views of the lakefront and downtown, along with excellent cocktails and small plates. A retractable roof makes it comfortable year-round.

One Off Hospitality opened a second location of its popular Mediterranean-inspired wine bar Avec last year in River North. With it also came a rooftop patio, dubbed Bar Avec, on the eighth floor of the same building. Complementing the stunning views is a menu that channels the Iberian Peninsula. Folks can enjoy items like smoked salmon conserva, clam toast, cheese plates, gin and tonics, and frozen daiquiris.

The large restaurant that specializes in large chunks of roasted protein has an elevated outdoor patio that offers one of the best downtown riverside views in Chicago. Diners can even take a water taxi right to the door.

Chicagoans can live their best lives at this swanky rooftop lounge and bar in the Gold Coast. Devereaux, located up high on the 18th floor of the Viceroy Chicago, combines sophisticated design with sweeping sightlines. The food and beverage program is equally impressive, boasting expertly crafted cocktails and elevated refreshments like truffle deviled eggs and Maine lobster sliders. There’s even a pool for those hot summer days.

This indoor/outdoor lounge on the third floor of the Renaissance Chicago Downtown Hotel overlooking the Chicago River has one of the city’s most scenic backdrops. Grab a seat on a cushy couch and snack on elevated bar bites, such as truffle frites, dilled cheese curds, house-made corn nuts, and cheese and charcuterie boards. The beverage program focuses on seasonal cocktails made with locally sourced ingredients as well as beers brewed in Chicago. There are also heat lamps on the patio to help keep things comfortable.

At Z Bar, the contemporary cocktail lounge on the Peninsula hotel’s sixth floor, one can sip a Manhattan served over ice that’s laced with 24-karat gold flakes and garnished with black truffle or saffron bitters. The cocktail list spans the globe in terms of flavors and spirits, while the terrace provides glowing views of the Mag Mile.

The stylish rooftop of the Chicago Athletic Association hotel is one of the hottest spots in town, with gorgeous views of Millennium Park and, beyond that, Lake Michigan. The cocktails and food are also top notch.

There aren’t many rooftops on the South Side so VU was a welcome addition when it opened in 2018. Located near Wintrust Arena and McCormick Place, the 13,000-square-foot space sits 22 stories above ground and has three bars, two patios, a karaoke room, outdoor fire pits, and retractable windows. Seasonal plates, such as ramp kimchi flatbread and green onion and crab dip, provide nourishment for guests as they sip on classic and specialty cocktails.

The views from this seasonal lakefront spot on the Ohio Street Beach are nearly unparalleled. Sit in the shadows of some of the city’s tallest buildings and dine on sandwiches, burgers, light starters, accompanied by a solid selection of libations, including fish bowls. Pups are welcome to join the fun, too.

Perched on the 70th floor of Lake Pointe Tower, Cité is big on the “wow” factor. The upscale restaurant features a breathtaking 360-degree view of the lakefront and skyline and is the perfect spot for an intimate and romantic evening. The menu showcases contemporary American fare with French influences, including escargot, lobster tail served with lobster ravioli, and bananas foster flambéed tableside.