Chicago’s Most Instagrammable Sites

You can visit many of the spots described below with eATLAS’ Adventures, such as the Chicago Art Deco Madness, Walk Around Wrigley Field, Museum Campus Scavenger Hunt, and Chicago, the Center of American Architecture.  

By Dave Lifton (@daveeatschicago)

Chicago’s picturesque downtown makes it ideal to broadcast the photos and videos of your vacation on Instagram through posts, stories, and reels. Start at Millennium Park, where Anish Kapoor’s Cloud Gate (“The Bean”) awaits, reflecting everything around in gleaming stainless steel. Be sure to capture the park’s other attractions, including Pritzker Pavilion, Crown Fountain and Lurie Garden, particularly in the summer. 

The warm-weather months are also an ideal time to show off the Riverwalk, a 1.25-mile hive of activity with restaurants, bars, and public art as tour boats pass by. The Riverwalk gives a perfect vantage point for landmarks like Marina City (the towers that look like corncobs), Jeweler’s Building, and Merchandise Mart. 

Walk past the Chicago Theatre (175 N. State St.) and there’s a good chance you’ll have to navigate through people posing for selfies. But the best spot is across the street, where you can get both the marquee and vertical sign in the same shot. And the best time is at dusk, when the lights will be on. 

Other photogenic structures in the Loop are the untitled sculpture by Pablo Picasso at Daley Plaza, the 600-foot Art Deco Chicago Board of Trade building, and Alexander Calder’s “Flamingo” in Federal Plaza. And don’t forget to catch video of an “L” train as it passes overhead. Better yet, get on the Brown Line towards Kimball and record the view as you cross over the Chicago River.

For interiors, a stop at the Chicago Cultural Center (78 E. Washington St.) is essential. Completed in 1897 as the city’s first permanent library, its most distinguished space is Preston Bradley Hall on the third floor. There, you’ll discover a Tiffany-built room filled with his distinctive lamps and mosaics, and a stained-glass dome with a 38-foot diameter, the largest he created. On the second floor is G.A.R. Hall and Rotunda, built as a meeting space for Civil War veterans. It has a 40-foot, 62,000-piece art glass dome in the Rotunda, and the Hall serves as a memorial to those who served. 

Nearby, the old Marshall Field’s store (now a Macy’s) has another gorgeous Tiffany installation, with 1.5 million pieces of glass. Pro tip: go to the fifth floor for a closeup view. Further down State is the Louis Sullivan-designed Sullivan Center (1 S. State St.), which is already a social media favorite as the “Goth Target.” That’s followed by the Palmer House Hilton (17 E. Monroe St.), whose lobby is the epitome of 1920s luxury and elegance, and where you can buy the brownie in the place where it was invented. 

There are many places you can go to catch the skyline in all its glory. Navy Pier is a perfect example, but possibly the best spot is on the grounds of the Shedd Aquarium on the Museum Campus. A few miles north of downtown, Lincoln Park has several incredible vistas: North Avenue Beach, the Honeycomb near the Nature Boardwalk at the Lincoln Park Zoo, and the bridge on Fullerton Ave. near Du Sable Lake Shore Drive. 

To get the highest views, visit 360 Chicago atop the former John Hancock Center or Skydeck on the 103^rd floor of the Willis Tower. If more than 1,000 feet above the city is too high for you, consider a rooftop restaurant, like Cindy’s at the Chicago Athletic Association Hotel or LH Rooftop at the LondonHouse Hotel. 

Sports fans will want to show off their trip to Chicago with a pair of pilgrimages. The first is Wrigley Field and its famous marquee on the corner of Clark and Addison. The second is the statue of Michael Jordan at the east entrance to the United Center. You don’t have to wait for an event to take a photo; the atrium is open from 10 a.m. to 5 p.m.  

But nothing on social media creates engagement like food. When going out for deep-dish pizza, be sure to take video of your server doing a perfect cheese pull. Show off the color contrast of our “dragged through the garden” hot dog or an Italian beef sandwich topped with hot giardiniera and dripping with au jus. Favorite local deserts include Garrett’s popcorn and the Original Rainbow Cone, where five ice cream flavors are stacked on top of each other. 

The author doesn’t update his food-centric Instagram account as often as he wants to because, too often, he doesn’t remember to take pictures until the meal is at least half-finished.