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One Perfect Night For Couples In Chicago

In a metropolis like Chicago, it’s an easy task to come up with an ideal date night—there’s much to do, see, and eat in the Windy City. From speed boat rides off of Navy Pier to Chicago Cubs games at Wrigley Field to shopping and dining on the Magnificent Mile to strolling hand-in-hand with your partner on The 606, you can undoubtedly craft an itinerary to suit your distinctive interests. For a fun night out with your loved one, or a rendezvous with another couple in tow, consider the below ideas.

Marvel at the Obama Portraits

Spanning centuries, the Art Institute of Chicago is home to some of the most compelling art in the world. Fresh exhibits are continuously on display to allure contemplative visitors all year round. This summer, Chicago is the very first city to host The Obama Portraits, organized by the Smithsonian’s National Portrait Gallery in Washington D.C., as they travel on a five-stop national tour across the country (Brooklyn, Los Angeles, Atlanta, and Houston are next). See Kehinde Wiley’s and Amy Sherald’s works-of-art in person, in the city where the Obamas first met, before it’s too late.

Pro Tips:

  • Download the Art Institute of Chicago’s free app to get in depth insights on the portraits from the artists themselves as well as from curator, Jordan Carter.
  • Learn about Wiley’s and Sherald’s portraits of President Obama and former First Lady Michelle Obama online with the museum’s Interactive Features. When scrolling through the pages, you’ll learn about 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 showcase how she portrays Black people from her community, shown with vibrant backgrounds without an exacting context.
  • Take as many photographs as you like but make sure that you do not use flash, video, tripods, or selfie sticks.

Clink Glasses on a Rooftop


One of the most quintessential Chicago experiences to have during the summertime is to sip cocktails on a rooftop with a view. Well-liked bars for rooftop season include: West Loop’s The Rooftop at Nobu Hotel, the Loop’s Cindy’s Rooftop, River North’s Z Bar, the Loop’s London House (LH) Rooftop,  and Streeterville’s Offshore.

A strong standout, however, is Upstairs at the Gwen in Chicago’s Loop, where you can indulge in craft cocktails, inventive noshes, and a tucked-in urban view. This Art-deco-inspired sanctuary in the clouds features fire pits, a multi-hued mural created by a local Chicagoan, and signature drinks like the Creole Maple Old Fashioned, Bramble, and Sweet Nothings.

Pro Tips:

  • Take your love of rooftop culture a bit further and join the Rise and Shine on the Terrace, a 60-minute Saturday morning yoga session, which includes a complimentary mocktail or cocktail at the end.
  • Bring your girlfriends to the Tipsy Tea Party, weekend Afternoon Tea, complete with finger sandwiches, intricate desserts, and boozy tea (or not), served between 12:00—4:00 p.m.

Dine Like a Star

Chicago has two dozen Michelin-starred restaurants, including three new ones: Chef Curtis Duffy’s Ever in Fulton Market, The Bar at Moody Tongue in Near South Side, and West Town’s Porto.  

For a distinctive culinary adventure and inventive Mediterranean fare, dine at Kostali by Naha, the brilliant brainchild of James Beard award-winning chef, Carrie Nahabedian and her cousin, Michael Nahabedian. The eye-pleasing interior design, with its cobalt enameled lava stone bar, nautically inspired golden metal screens and global satellite imagery, will transport you to the coastal shores of Spain, Italy, France, Greece, Tunisia, Lebanon, Israel and Morocco. The menu, of course, reflects the restaurant’s character. Order Hallumi or Spanish Octopus for a starter, Striped Bass, or Parisian Gnocchi for your main, and Loukoumades for dessert. And, whatever you do, don’t skip out on the rustic bread served with a roasted pepper and eggplant spread.

Pro Tip:

  • Kostali’s private event space is sure to fit the bill for your special outing, should your group desire a more intimate space. The nine-seat bar and lounge area can also be reserved.

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