Answers from Our Experts (1)
Because there are so many amazing restaurants and activities in every neighborhood in the city, the answer to this question begs another: What’s your style?
Classic: Dinner and a Show in the West Loop
I’d recommend nabbing reservations at one of the dozen or so outstanding restaurants on Randolph Street’s Restaurant Row, and then walking to City Winery to catch a concert with cabaret-style seating. I recently enjoyed a West Loop date-night just like this, starting at Executive Chef Paul Kahan’s Avec (go early; this is one of the few that doesn't take reservations and fills up by 6 p.m. nightly) followed by a concert that was underway by 8 p.m. down the street.
Trendy: Al Fresco Dining in Wicker Park
Booking a night out in trendy Wicker Park is a wonderful excuse to explore a neighborhood that comes to live after sunset. Many cafes and restaurants along Milwaukee Avenue offer sidewalk seating for dinner (I like Taxim, specializing in modern Greek fare), and just as things begin to get a little rowdy, it’s time to steal away to darkly lit cocktail den The Violet Hour, where expertly mixed drinks await.
Romantic: Picnic in Millennium Park
If the weather allows it, I love nothing more than a gourmet picnic date under the stars at Millennium Park, whose Jay Pritzker Pavilion hosts live music of all stripes through the summer months. If you’re hankering for a nightcap once the concert ends, Henri on Michigan Avenue is a beautiful little French-inspired fine dining restaurant with a perfect little bar. Alternatively, at the north end of the park lies Maison, an often overlooked little bistro with a lovely selection of wines and digestifs.