Sightseeing in Chicago

Content originally written for the Let’s Go: USA & Canada Guide by our researcher-writer, Daphne Thompson.

Chicago Cultural Center

78 E Washington St.; (312) 744-3316;; open M-F 10am-7pm, Sa-Su 10am-5pm

Don’t be fooled by the “Chicago Public Library” engraving on this very library-looking Loop venue—we looked hard and long for a book in the Cultural Center, and couldn’t find a single one. We did find, however, one of the city’s 100% free art galleries, showing a small but well-curated group of exhibitions with Chicago roots. A portion of Keith Haring’s genuinely moving Chicago Mural, painted by 500 area high school students on 1989, is on display through September, as is Alexis Rockman’s eco-conscious series of Great Lakes paintings (they’re equal parts grotesque and gorgeous). While a lot of the building is eerily vacant—it’s mostly used as an event space—it’s architecturally interesting enough to merit a quick meander. Look for the world’s largest Tiffany stained-glass dome, and just imagine how great it would be to hurl a rock through it.

Free; tours W-Sa 1:15pm; Wi-Fi; wheelchair accessible

Magnificent Mile

Michigan Ave.; (312) 409-5560;; establishment hours vary

If you were the king of Chicago trying to impress your foreign rivals, the Magnificent Mile is where you’d want to have the welcoming parade. The River North stretch of Michigan Avenue is lined with some of the city’s finest architecture (the Tribune Tower, the Wrigley Building), most luxurious stores (Bloomingdale’s, Louis Vuitton), and slowest-walking tourists (Karen, Jim). While there are some backpacker-friendly options like H&M scattered throughout the street, it’s more fun to go into Gucci and see how much stuff you can touch before the security guy starts watching you. As far as food, two porky options stand out: a Portillo’s hot dog is a dependable cheap standby, and The Purple Pig serves Michelin-approved tapas if you’re looking to splurge.  

Free; wheelchair accessible

Navy Pier

600 E Grand Ave.; 1-800-595-7437;; opens 10am, view website for closing times

Navy Pier is having a bit of an identity crisis. Is it an old-school amusement park? A sleek foodie destination? A meeting point for every balloon artist in the Chicagoland area? Predictably, the longtime Near North Side tourist attraction tries to please everyone, and ends up half-assing most of it: The ferris wheel is overpriced ($18 a ride) and underwhelming, and the food court is outclassed by the enormous selection of nearby local restaurants. The 100-year-old park’s moves to modernize have stripped the once rough-around-the-edges pier of most of its character, replacing cute, kitschy shops with chain restaurants and Instagram bait. Still, the Chicago Shakespeare Theater remains a gem of the Midwest, and the simple pleasure of strolling the boardwalk at sunset —strawberry churro in hand—is undeniable.

Free; wheelchair accessible

Chicago Water Tower

806 Michigan Ave.;; open M-F 10am-7pm, Sa-Su 10am-5pm

We haven’t seen waterworks this pretty since Timothée Chalamet at the end of Call Me By Your Name. The Gothic Revival structure on an extra-bougie stretch of Michigan Ave. looks like it should be housing a small princess instead of a large water pump, its original purpose when it was built in 1869. It survived the Chicago Fire of 1871 and became a symbol of hope for people who had lost, like, their houses—Midwesterners are an optimistic bunch. Today, it’s home to a piddly art gallery, a fine photo op, and a pit stop on The Amazing Race once in a while. Stop by on your Magnificent Mile walk and marvel at the city’s super dope dedication to public infrastructure projects.

Free; wheelchair accessible

Tribune Tower

435 N Michigan Ave.; (312) 222-3787;

Once one of the world’s finest temples to the First Amendment, the Near North Side’s Tribune Tower is today much more like those clickbaity square cooking videos on your Facebook feed: beautiful but hollow, and somehow deeply sad. The Gothic revival skyscraper, proclaimed “the world’s most beautiful office building,” housed the Chicago Tribune from the 1920s until 2018 when the building changed hands and the journalists decamped for Millennium Park. It’s being converted into a luxury condo building, but for now, you can still visit the lobby—inscribed with testaments to the power of the press—and traverse the exterior, which is embedded with over 100 significant rocks. Look for hunks of the White House, the Great Wall of China, the Taj Mahal and even the moon stuck into the stone.

Free; wheelchair accessible

Willis Tower

233 S Wacker Dr.; (312) 875‐0066;; summer open daily 9am-10pm, winter open daily 10am-8pm

The building formerly known as the Sears Tower is going through a weird time right now—its new owners are pumping $500 million into renovations, but it’s currently in an awkward transitional phase more welcoming to office workers than tourists. If you like getting really high, though, you can still ascend to the near-top of the country’s second-tallest tower (darn it, One World Trade Center!). The Skydeck is a well-worn stop on the tourist track, offering terrifying views from 103 stories up; on a clear day, you can see clear across Lake Michigan. The truly ballsy will venture out onto the glass-bottomed ledge to look down at the streets below—the floor did crack once a few years ago, but no one was hurt, so try not to think about it?  

Skydeck admission $24; wheelchair accessible

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