The most romantic restaurants in Chicago to book for date night

What is it? A high-end Italian restaurant and bar inside the St. Regis.

Why we love it: Crowned the most beautiful restaurant in Illinois, Lettuce Entertain You's gorgeous Tuscan steakhouse is one of the hottest spots in town. If you're fortunate enough to snag a reservation, prepare to wine and dine in style. Guests pass by a pasta lab—where tortelli, spaghetti and tagliatelle are crafted—on their way into the dining room, which offers stunning skyline views. The steaks are all cut to share, so combine them with plates like short rib meatballs and blue prawns in salsa verde, or chef Evan Funke's excellent pastas.

Time Out tip: Request a table by the soaring window to take advantage of the sweeping city views—and really wow your date.

Address: 401 E Wacker Dr, Chicago, IL 60601

Opening hours: Mon-Thu, Sun 4-9:30pm; Fri, Sat 4-10:30pm

What is it? Chef César Murillo’s cozy restaurant, tucked next to a pond within Lincoln Park.

Why we love it: On the northern end of the North Pond Nature Sanctuary sits a lovely farm-to-table restaurant that’s every bit as charming as it is delicious. Housed in a building that was constructed in 1912 to be a warming shelter for ice skaters, North Pond now serves as one of the most romantic dining rooms in town. The skyline views are the cherry on top.

Time Out tip: For a more affordable option, opt for the Sunday prix fixe brunch, which is priced at $59 per person.

Address: 2610 N Cannon Dr, Chicago, IL 60614

Opening hours: Thu 5:30-8pm; Fri, Sat 5:30-9pm; Sun 10:30am-1pm, 5:30-8pm

What is it? Brendan Sodikoff’s vaguely French steakhouse.

Why we love it: While Sodikoff’s other spots (Gilt Bar, Au Cheval) have their charms, the appeal of this spot—decked out with jazz-era decor and music—is practically universal, and perfect for a cozy evening with your significant other. Diners need not be huge steak fans to get a good meal—in fact, as good as the steak frites is, both the fried and roasted chicken are even better. 

Time Out tip: If you really feel like treating your date, you can split one of the seafood towers.

Address: 218 W Kinzie St, Chicago, IL 60654

Opening hours: Mon-Thu 4-10:30pm; Fri, Sat 3-11pm; Sun 3-10:30pm

What is it? A dimly lit fondue den in Lincoln Park.

Why we love it: Geja's Café is a reliably romantic date destination. The four-course Prince Geja Combination, while pricey, allows couples a chance to get cozy while experimenting with various dips. A cheese fondue appetizer with bread, grapes and apples is followed by a house salad. Then, beef tenderloin, chicken breast, lobster tail, jumbo shrimp and sea scallops are brought out to be cooked in the tableside hot oil pot. Lastly, a Belgian chocolate fondue served with sweet treats caps things off. We consider that dinner and a show!

Time Out tip: If you're looking for a date night at home, pick up one of Geja's to-go kits, which come with everything you need for a DIY fondue night.

Address: 340 W Armitage Ave, Chicago, IL 60614

Opening hours: Mon-Thu 5-8:45pm; Fri, Sun 4-9:45pm; Sat 3-9:45pm

What is it? The fine-dining beacon that started Boka Restaurant Group, one of Chicago's finest culinary collectives.

Why we love it: Boka has long been a paradigm of fine dining in the local scene. The warm and elegant space is fit for both a romantic date night and a special occasion. Culinary maestro Lee Wolen is the mastermind behind the menu, which focuses on seasonal American cuisine. His talents are on full display with the whole roasted dry-aged duck, a remarkable dish—featuring juicy, tender meat under crisp skin—that's entirely shareable.

Time Out tip: Avoid sitting at a table in the bar area if possible, as it’s so loud that we couldn’t hear our servers on a recent visit, and the elaborate garden wall in the other dining room is something to behold.  

Address: 1729 N Halsted St, Chicago, IL 60614

Opening hours: Mon-Thu, Sun 5-9pm; Fri, Sat 5-10pm

What is it? One of the most beautiful and opulent restaurants in Chicago.

Why we love it: There’s no better reason to get dressed to the nines than having a swanky dinner at BLVD Steakhouse. The space is inspired by Hollywood’s Golden Age, so expect touches like crystal chandeliers and a grand staircase. Culinary director Joe Flamm complements the sophisticated setting with luxuries such as seafood towers and dry-aged cuts of beef. If you’re really looking to impress your date, splurge on caviar service. 

Time Out tip: We suggest adding grilled king crab leg to the beef because why not? 

Address: 817 W Lake St, Chicago, IL 60607

Opening hours: Mon-Thu 4:30-10pm; Fri 4:30-11pm; Sat 10am-11pm; Sun 10am-10pm

What is it? Chef-owner Erick Williams' Southern American spot in Hyde Park. 

Why we love it: Virtue specializes in Southern cuisine and seriously sexy vibes. The lights are turned down low, the playlist is always on point, the food is filled with soul and the menu boasts some excellent wines by the glass and bottle. Couples are best suited ordering a few appetizers and sides to share plus their own entrees. 

Time Out tip: Save room for banana pudding studded with Nilla wafers, and request a round of Champagne with Williams.

Address: 1462 E 53rd St, Chicago, IL 60615

Opening hours: Tue-Thu, Sun 4-9pm; Fri, Sat 4-10pm

What is it? The closest you can get to the Tuscan countryside without hopping on a plane.

Why we love it: Get away from the hustle and bustle of the city by heading to Piccolo Sogno’s lush, fenced-off garden oasis when the weather permits. Tony Priolo showcases the rustic flavors of Italy through pastas, pizzas and other staples such as bistecca alla griglia. 

Time Out tip: Ask your server for a recommendation on a bottle from the extensive Italian wine list for an impeccably romantic experience.

Address: 464 N Halsted, Chicago, IL 60642

Opening hours: Mon-Thu 11am-2:30pm, 5-9pm; Fri 11:30am-2:30pm, 5-9:30pm; Sat 4-9:30pm; Sun 4-9pm

What is it? An intimate Italian supper club.

Why we love it: Hogsalt Hospitality has a knack for creating transformative spaces that are stunning and memorable. At Ciccio Mio, the company nails the romantic look and feel with dim lighting, ornate furnishings and vintage-style artwork on the walls. The food’s no slouch, either, boasting favorites like spicy vodka rigatoni, lasagna rolls and chicken parm. 

Time Out tip: If you and your date still have room at the end, the cannoncini will provide a perfect finish.

Address: 226 W Kinzie St, Chicago, IL 60654

Opening hours: Mon-Thu, Sun 4-10:30pm; Fri, Sat 4-11pm

What is it? A luxe Italian steakhouse and event space.

Why we love it: There are three floors to explore at this modern riverfront steakhouse, which deals in premium cuts, decadent handmade pastas and classic Italian eats. The handsome dining room is hard to forget, but as soon as you see the views—an eyeful of the Chicago River and world-class architecture—you might have trouble concentrating on your date. Center the conversation with a bottle of bubbly and an order of tiramisu.

Time Out tip: Gibsons Italia offers one of the most unique views of the city, right where the river splits north and south.

Address: 233 N Canal St, Chicago, IL 60606

Opening hours: Daily 11am-11pm

What is it? A romantic Logan Square wine bar and steakhouse.

Why we love it: The Spanish word "penumbra" translates to "partial darkness," which is a fitting name for this dimly lit spot that locals flock to. Penumbra's menu is approachable with a curated selection of pours available by the glass as well as a laundry list of bottles to choose from. The dinner menu offers more than small snackables with a lineup of steaks, seafood, hearty vegetarian dishes and a handful of desserts.

Time Out tip: Stop by on Wednesday from 5 to 6:30pm for half-off glasses of wine.

Address: 3309 W Fullerton Ave, Chicago, IL 60647

Opening hours: Wed 5-10pm; Thu, sun 5-9pm; Fri, Sat 5-11pm

What is it? A dreamy Italian eatery from Boka Restaurant Group.

Why we love it: Italian food is always going to feel a bit romantic (especially when it's accompanied by a nice bottle of wine), but if you really want to heighten the mood, the magical decor at Alla Vita should do the trick. Yes, it's a difficult reservation to get, but a wonderful night with your main squeeze is worth the trouble.

Time Out tip: Couples can share a pizza or dig into the exquisite chicken parmigiana—both of which are perfect for two.

Address: 564 W Randolph St., Chicago, IL 60661

Opening hours: Mon-Fri 11am-2pm; Sat, Sun 4:30-10pm

What is it? Andrew Zimmerman's Michelin-starred stalwart in the West Loop.

Why we love it: Sepia is a destination for constantly changing dishes like wagyu beef tri tip with Asian pears; foie gras custard and cabbage; and lemon doughnuts with grapefruit curd and cardamom. The bar program, under Keith Meicher, turns out well-balanced drinks, while the globe-trotting wine list highlights bottles you likely won't find elsewhere. 

Time Out tip: The four-course prix fixe menu is only $125 per person—one of the most affordable Michelin-starred experiences in Chicago.

Address: 123 N Jefferson St, Chicago, IL 60661

Opening hours: Mon-Thu 5-9pm; Fri, Sat 5-10pm

What is it? Chef Soo Ahn's glitzy Italian dining room.

Why we love it: Come dressed to impress because the servers certainly bring the fashion. Adalina's elegant dining room sports sophisticated touches, such as crystal chandeliers and vintage mirrors, while chef Soo Ahn presents luxurious options like a truffled Caesar salad, A5 wagyu and caviar service. 

Time Out tip: After dinner, head downstairs for a drink at the Rose Lounge, a small and intimate cocktail den.

Address: 912 N State St, Chicago, IL 60610

Opening hours: Mon-Wed 4-10pm; Thu, Fri 4-11pm; Sat 3-11pm; Sun 3-10pm

What is it? One of the toughest reservations in Chicago.

Why we love it: To book a reservation at Armitage Alehouse, you’ll need to be refreshing on the dot at 9am—and hope for a fair bit of luck, too. Pull it off, though, and you'll be treated to fancy takes on British pub fare, ranging from fish and chips to pot pies, plus the mild curries and chutneys of Anglo-Indian cuisine  Armitage Alehouse is an ode to 1920s British pubs, with an interior lined with antique oil paintings, ornate sconces and other vintage touches, making it the ideal spot for date night.

Time Out tip: You might try walking in on a Tuesday or Wednesday night if you weren't able to get a reservation.

Address: 1000 W Armitage Ave, Chicago, IL 60614

Opening hours: Mon, Tue 4-10pm; Wed, Thu 11am-10pm; Fri 11am-10:30pm; Sat 10am-10:30pm; Sun 10am-10pm