What to Eat, See and Do during an Upscale Summer Staycation in Chicago

By Laura Hine | July 3, 2019 | Lifestyle

With so much to see and do in Chicago in the summertime, the question is: Why would you ever leave? You can have the perfect vacation without even departing the city: Miles of sandy beaches are mere steps from the Loop’s skyscrapers. You can walk from your last meeting of the day and be on the lake or river in minutes. To soak up every drop of summer, there are rooftop bars and alfresco dining spaces galore. And since the city is one of the most walkable in the world, you and yours have public art and window-shopping aplenty to amuse you on your ambles.


A guest room at Hotel Essex (Photo by Nicholas James/courtesy of Hotel Essex)

The newly renovated and transformed Hotel Essex occupies a primo spot along Chicago’s Cultural Mile, which means it looks out over Grant Park (home of Lollapalooza every August), and it’s a stroll from Millennium Park (selfie with “The Bean”) and the Art Institute (note that Renzo Piano’s Modern Wing just celebrated its 10th anniversary). The hotel’s floor-to-ceiling windows and sweeping vistas make it easy to plot your day with a glance outside.


Virgil Abloh, "You're Obviously in the Wrong Place," 2015/19 photo courtesy of the artist/MCA

In addition to the attractions along the Cultural Mile, no Chicago staycation is complete without paying homage to the city’s architecture. Start at the Chicago Architecture Center’s new space. Combine a stroll through the skyscraper and city-planning exhibits with the Chicago Architecture River Tour. To bask in the rays, sit on the top deck; you’ll also get the best view of iconic buildings by Ludwig Mies van der Rohe, Jeanne Gang and Bertrand Goldberg.

To add a little star power to your sunny day, queue up for this summer’s blockbuster at the Museum of Contemporary Art. Virgil Abloh: “Figures of Speech,” which covers Abloh’s career across music, fashion, architecture and design, is a must-see with must-purchase items—the merch is as hot as the exhibit.


The sun-drenched patio at Beatnik on the River channels a tropical vibe. (Photo by Francis Son/courtesy of Beatnik on the River)

You’ll need some sustenance to keep up this sun-chasing pace, so post-cruise, head to Beacon Tavern, which has a lovely terrace and Southern-inspired menu. If you want aquatic views, Beatnik on the River has a boho-chic terrace overlooking the water and globally inspired dishes that match the exotic decor. Or head to the West Loop where the just-opened Bandit has a menu with crowd-pleasers like Disco Waffle Fries topped with bulgogi-braised short rib.

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