The Sexiest Restaurants in the Windy City, As Picked by Chicago’s Top Relationship Expert

Where to head, whether it’s your first date or something slightly more serious

November 29, 2022 7:00 am
Couple on dinner date night eating healthy food with quinoa salad and drinking red wine
Some of Chicago's best date spots - for any kind of couple
wundervisuals via Getty

Chicago dating expert Bela Gandhi knows a lot about love. As the founder and president of Smart Dating Academy — and the presenter behind TEDxChicago’s paradigm-shifting The Big Secret to Finding Lasting Love — she’s essentially Chicago’s relationship expert. If anyone knows sexy, it’s her — and she was kind enough to share her recommendations for the sexiest restaurants in the Windy City. From the first date to your diamond anniversary, there’s something here for everybody. 

For a first date: Gilt Bar

Why we think it’s sexy: Gilt Bar is super sexy, with its low lighting and leather couches. Sneak into Gilt Bar’s Library via the basement side door — you’ll enter a speakeasy with velvet booths, chandeliers and books upon books. If it’s your first date, try sitting side-by-side, European-style, at the bar or grab a small two-top, sharing a cocktail (we recommend the espresso martini, which is made with Mr. Black liqueur, Skyy Vodka, a cold brew concentrate, vanilla and cocoa bitters). If the date is going well, stay for dinner. They offer handmade pasta — the Truffle Bucatini is so delicious, it’ll make anyone fall in love. 

Details: Gilt Bar, 230 W Kinzie St., Chicago

For a third date: 3 Arts Club

Why we think it’s sexy: You’re dining under a glass-and-steel atrium in downtown Chicago surrounded by fountains, olive trees and chandeliers, thanks to Restoration Hardware’s imaginative play on a coffee house/wine bar/restaurant that is hidden within the fancy furniture store. Play house and shop for furniture, or just browse and fantasize while sipping a glass of wine. After your shopping sojourn, sit in the atrium and feel like you’re transported to a European garden.

Details: 1300 N Dearborn St., Chicago 

For an anniversary: Alpana

Why we think it’s sexy: Three words: wine-inspired cuisine. At this chic, relaxed spot in Chicago’s historic Gold Coast, the dishes complement the international selection of wines. And who better to create the concept than Alpana Singh, the owner, sommelier and former host of Check Please? Dig into the squid ink campanelle, and share the striped sea bass while sipping on perfectly paired vino. The bistro is light and airy, with floor-to-ceiling windows, mirrors, plants and plenty of photos of women who are meaningful to Singh. It looks like your dining room might look — if your dining room were uber-sexy. 

Details: 831 N State St., Chicago

For an anniversary: Tao Asian Bistro & Nightclub

Why we think it’s sexy: From the moment you push on those gigantic wooden front doors and enter the massive boisterous space, you know you’re in for a different evening. We felt like we were transported out of Chicago and into Vegas — in a good way. It’s loud, but you can still hear your table-mates perfectly; it’s dark enough to feel incredibly sexy, and the food is better than we ever imagined. When you’re done eating, wander upstairs to the nightclub to dance the night away. 

Details: 632 N Dearborn, Chicago

For an engagement: Aviary Kitchen Table

Why we think it’s sexy: When you combine the best chefs in the business with the most creative mixologists in the world, you get Aviary. The winner of awards ranging from James Beard for outstanding bar to Drinks International’s World’s Best Bars, this is the place to be to be wowed. You’ll watch, eat and drink concoctions that will blow your mind with smoke, ice and everything in between. 

Details: 955 W Fulton Market, Chicago


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