In a metropolis like Chicago, it’s easy to find the perfect date night: there’s plenty to do, see, and eat in the Windy City. From speedboat rides departing from Navy Pier to Chicago Cubs games at Wrigley Field, to shopping and dining on the Magnificent Mile, to hand-in-hand rides with your partner on 606, you can undoubtedly create an itinerary to suit your particular interests. For a fun night out with your loved one or a date with another couple, consider the ideas below.
Marvel at the portraits of Obama
Spanning centuries, the Art Institute of Chicago is home to some of the most fascinating arts in the world. New exhibitions are continually on display to appeal to contemplative visitors all year round. This summer, Chicago is the very first city to welcome Obama portraits, hosted by the Smithsonian’s National Portrait Gallery in Washington DC, as they complete a five-stop nationwide tour across the country (Brooklyn, Los Angeles, Atlanta and Houston are next). See the artwork of Kehinde Wiley and Amy Sherald in person, in the city where the Obamas first met, before it’s too late.
- Download the free app from the Art Institute of Chicago for detailed information on the portraits of the artists themselves as well as the curator, Jordan Carter.
- Discover Wiley and Sherald’s portraits of President Obama and former First Lady Michelle Obama online with the museum’s interactive features. As you flip through the pages, you’ll learn how Wiley became the first black artist commissioned by the National Portrait Gallery to paint a president. You’ll also see other works in Sherald’s portfolio that show how she portrays black people in her community, shown with vibrant backgrounds with no demanding context.
- Take as many photos as you want, but make sure you’re not using a flash, video, tripod, or selfie stick.
Clink Glasses on a roof
One of Chicago’s most typical summer experiences is sipping cocktails on a rooftop with a view. Top-rated rooftop bars for the season include: The Rooftop at West Loop at the Nobu Hotel, Cindy’s Rooftop at Loop, Z Bar at River North, The Rooftop of London House (LH) at Loop and the Streeterville offshore.
However, the Upstairs at the Gwen in Chicago’s Loop is a must-see, where you can enjoy handcrafted cocktails, inventive dishes, and a tucked-away city view. This Art Deco-inspired sanctuary in the clouds features fireplaces, a multi-colored mural created by a Chicago resident, and iconic drinks like Creole Maple Old Fashioned, Bramble, and Sweet Nothings.
- Take your love of rooftop culture one step further and join the Rise and Shine on the Terrace, a 60-minute yoga session on Saturday morning that includes a mocktail or cocktail at the end.
- Bring your girlfriends to the Tipsy Tea Party, the weekend afternoon tea, with finger sandwiches, complex desserts and alcoholic tea (or not), served between 12:00 p.m. and 4:00 p.m.
Dine like a star
Chicago has two dozen Michelin-starred restaurants, including three new ones: Ever by Chef Curtis Duffy at Fulton Market, The Bar at Moody Tongue on the Near South Side, and West Town’s Porto.
For a distinctive culinary adventure and inventive Mediterranean cuisine, dine at Kostali by Naha, the brainchild of award-winning chef James Beard, Carrie Nahabedian and her cousin, Michael Nahabedian. The attractive interior design, with its cobalt-enamelled lava stone bar, nautical-inspired gold-tone metal screens and global satellite imagery, will transport you to the coastal coasts of Spain, Italy, France , Greece, Tunisia, Lebanon, Israel and Morocco. The menu, of course, reflects the character of the restaurant. Order hallumi or Spanish octopus for a starter, striped bass or Parisian gnocchi for a main course and loukoumades for dessert. And, whatever you do, don’t skip the rustic bread served with a grilled pepper and eggplant spread.
- Kostali’s private event space is sure to be suitable for your special outing, if your group wants a more intimate space. The bar and the nine-seat lounge can also be booked.