Take in sweeping views of the Chicago River at Gibsons Italia, a modern Italian steakhouse. The glam, tri-level dining room is decked with sleek marble tables and rich leather chairs—the perfect setting for a luxe feast of caviar, gold-extruded pastas, and world-class steaks like a 34-ounce wagyu tomahawk with optional black truffle butter. For the best views, head to the scenic rooftop deck.

One of Chicago’s most beautiful restaurants, Aba brings Mediterranean vibes to the West Loop. Get river views from the expansive rooftop patio, decked with potted plants and low-slung sofas—ideal for digging into chef CJ Jacobson’s made-for-sharing menu. Start with the hummus served with warm housemade bread before moving on to mezze, kebabs, and standouts like chargrilled lamb chops. The playful drinks menu includes a build-your-own-spritz tower and stellar zero-proof cocktails.

Located inside the chic Hoxton hotel, Cabra is what rooftop restaurant dreams are made of—peak skyline views and family-style, Peruvian dishes developed by Chicago chef legend Stephanie Izard of Girl & the Goat. Sit in the sunny dining room with floor-to-ceiling windows and hanging greenery to feast on shareable snacks like shrimp ceviche, yucca fries, and Izard’s signature goat empanadas. Don’t miss the restaurant’s rotating selection of frozen pisco.

Head to the glitzy Rooftop at Nobu Hotel for killer views and luxe Japanese- and Peruvian-accented dishes from star chef Nobu Matsuhisa. With low-slung, modernist furniture and greenery, the sleek restaurant is ideal for large groups and lively celebrations. Come at happy hour for fancy bar bites like wagyu sliders and specialty cocktails like a lychee and elderflower martini. The elegant dinner menu stars sushi, nigiri, and hot dishes like lobster tempura truffle amazu.

Soak in breathtaking views of Lake Michigan and the river through dramatic 40-foot windows at Tre Dita, star LA chef Evan Funke’s swanky Tuscan-style steakhouse inside the towering, 101-story St. Regis. Outfitted with arched portals, marble accents, and walnut timber paneling, the glam dining room is a special-occasion destination for its wood-fired steaks, elegant handmade pastas, and 700-plus-bottle, all-Italian wine list.

“Miru” is Japanese for “view,” and this sophisticated spot at The St. Regis Chicago delivers. Choose from the serene, modernist dining room or two expansive decks for views of Navy Pier and the Chicago River. Either way, you’ll feast on stellar sushi and fancy, Japanese-leaning dishes like robata skewers, lobster spring rolls, and wagyu tartare. Linger with a glass of wine or sake from the extensive drinks list.

Utopian Tailgate is just that—a sprawling, indoor-outdoor playground for the 21 and over crowd. Grab a hanging chair or picnic table for the crew to cheer on your favorite team on one of the massive TVs, or play lawn games like life-sized Jenga. The laid-back menu—think nachos, wings, and sandwiches—lean into the tailgating theme. So do the drinks, which include beer packs and large-format cocktails ideal for groups.

Tanta is a date-night favorite for its heated, year-round patio and top-notch Peruvian-inspired menu. Grab a seat on the sleek rooftop deck dressed with greenery for prime skyline and river views. Then dig into ceviches, anticuchos, and shareable platters like a grilled branzino, all served on dishes as vibrant as the food. Or go all out with the chef’s tasting menu. Bonus points for standout cocktails, including several takes on the pisco sour, Peru’s national drink.

Since opening in 2010, Chicago Cut Steakhouse has become a celebrity and local favorite for its sophisticated surf-and-turf menu and prime riverfront location. Grab a seat in the elegant, wood-paneled dining room or on the elevated outdoor patio to feast on premium cuts of beef dry-aged on-site, along with steakhouse classics like lobster tails, oysters on the half shell, and a standout wedge salad. Add in a 600-bottle wine list, and you have all the makings for a fancy night out.