Why is it so hard to pick the ten best places in Chicago, IL to visit? Because with historic landmarks and spectacular buildings, Chicago’s neighborhoods are freckled with ornate, beautiful facades, vintage jewel-box interiors, and timeless architecture – there are many noteworthy landmarks around every corner. Scout any stretch of road and you’ll find groovy places referenced in pop culture or hip areas to see and be seen. Even better, in Chitown, locals are friendly and funky. Happily for those hunting for the best places in Chicago to visit from theaters, museums and movie houses to cemeteries, concert halls, and cinematic locations, we’ve got ten top picks to begin your adventures at – just some of many great stopovers the city offers.
With its bright marquee and triumphal arch, the Chicago Theater is a clarion symbol of the Windy City, and a fantastic spot to catch a concert, comedy act and more (basically, everybody’s played here). Opened some 90 years ago as a cinema and revived, restored and now thriving, the theater’s French Baroque interiors are marvels. The lobby ceiling shoots 50 feet in the air, and the grand staircase glides you up to the impressive auditorium itself, which rises 70 feet and is adorned with murals, stunning lights and crystal chandeliers. The space seats 3,600, and even if you don’t catch a show here — though we recommend you do — a tour is more than worth your time.
In Uptown, the 150-year-old Graceland Cemetery encompasses 120 acres of greenery, mausoleums, tombstones and monuments to Chicago’s permanent residents. Take time and wander here: During winter, grab a coffee nearby as snow falls and you seek out the graves of famed architects such as Louis Sullivan and Mies van der Rohe, or scope the incredible Getty Tomb. A bit north, the 350-acre Rosehill Cemetery, a National Landmark site, is home to the Rosehill Mausoleum, with Tiffany windows and lots and lots of marble. Rosehill is a particularly bonkers spot for Civil War fans, as it is the final resting place of more than a dozen generals and several hundred Union soldiers.
You can’t miss the Marina Towers, called the corn cobs by locals, rising from this densely packed spot on the Chicago River. These iconic buildings reach skyward in popular culture, too: You probably recognize them immediately from Wilco’s 2002 album cover, “Yankee Hotel Foxtrot.” They were groundbreaking: Among other firsts, the towers were the first buildings ever to use tower cranes in construction, and the apartments inside are all electrically powered (no gas). Enjoy what the mixed-use acreage offers in the way of entertainment, too: Catch music at the House of Blues and dine at exquisite spots with river frontage, like Smith & Wollensky. Boats dock close by at the marina (hence the name), and the towers, once the sun goes down, are particularly beautiful sights to see.
The MCA, in Streeterville, will sate your craving for modern and cutting-edge art, with its collection of about 2,700 works (think Calder, Warhol, Jasper Johns, along with Koons, Bacon and Rauschenberg, to name a few). Also hosting performance arts including multimedia works, dance, music, a summertime farmer’s market as well as theatre and film (the museum houses a fairly large multipurpose theater), it’s an eclectic place. In the MCA’s newer structure, completed in 1996, is an education center, shop and sculpture garden with airy views. This place’s cool quotient is almost unparalleled: It was the only U.S. venue to stage the “David Bowie Is” traveling exhibit a few years ago and, in summer 2017, it hosted Takashi Murakami’s “The Octopus Eats Its Own Leg.”
Stretching 1,000 yards into the blue of Lake Michigan, Navy Pier basically is the largest draw in Chicago (and maybe the Midwest). With rides, a carousel, a giant ferris wheel, the Chicago Funhouse Maze, the Chicago Shakespeare Theatre, an indoor skating rink around the holidays, summer fireworks, all-weather parks, places to shop, eat and listen to live music, it’s also hard to miss. Insiders like it because it’s fun, busy and at times a little crazy. A must-visit if you want some free excitement on a nice day.
In the northern suburb of Wilmette, the intricate dazzle of the Baha’i House of Worship towers over gardens, fountains and green-lined pathways. Its gorgeous, domed temple is nothing short of awe-inspiring: Free to the public, and open daily, this nine-sided structure took 30 years to build and is on the National Register of Historic Places. The sound of running water is everywhere here, and flora abounds. The tranquil surroundings are also a draw for both locals and out-of-towners (the grounds offer a great place to view holiday fireworks). In Wilmette, you’re also in John Hughes territory; venture around the surrounding neighborhoods to find locations from your favorite ’80s flicks.
Want to see a play? Go to any of these three famous gems. The Goodman Theatre, Chicago’s oldest, is in the Loop and can’t be beat — it’s world-renowned and features major-league talent. Victory Gardens Theatre, now housed in the refurbished Biograph Theatre (where John Dillinger was taken out), specializes in developing new works by emerging authors. Steppenwolf, founded by a trio of actors including Gary Sinise, is in Lincoln Park, and has been the stage on which many plays got their start before migrating toward the Big Apple and on to wider acclaim.
For the blues, there are two must-visits in Chicago: In Printer’s Row, Buddy Guy’s Legends, which famously keeps the flame alive, and Rosa’s Lounge in Logan Square, a little gem that locals seem to pass right by. Supposedly, Muddy Waters asked Guy to keep the tradition of the blues from dying, and Legends continues that work. The cover may be steep, but the acts are top-shelf, the memorabilia’s awesome (and so are the patrons, including the Rolling Stones, who paid the spot a visit), and the food is superb. While Rosa’s doesn’t serve grub, it does offer up authentic Chicago blues acts in a cozy, intimate setting. With cheap drinks and a cover that’s usually less than $10, you’ll likely leave very late and very satisfied with the bluesy sound.
Home to the Joffrey Ballet, and playing host to the Alvin Ailey Dance Company, the Bolshoi ballet, musicals and even the NFL Draft, the Auditorium Theatre, opened in 1889, is second only to New York’s Metropolitan Opera in terms of size (it seats nearly 4,000). Hendrix played here. So did Bowie, Janis Joplin and Springsteen. It has perfect acoustics, and there isn’t a bad seat in the glowing, gold-trimmed house. Inside are mosaics, murals and ornate glass windows, damasked carpets and fine ironwork ornaments. One of the most dazzling elements is the stage’s shell-like ring of lights; the exposed filament bulbs lining it, and the theater’s surrounding thousands of clear-glass bulbs, were historic innovations in their day. Tour this place, even if it’s the off-season.
Whether you’re after a recent release, indie flick, a foreign film, a Hollywood classic, cult fave or restored print, catch a movie here. Nearly 100 years old, the Music Box (you can’t miss the old-school vertical marquee and gorgeous facade), is one of the coolest spots for cinema. It’s a performance space as well, hosting festivals, midnight movies and series discussions for celluloid junkies. Buy a ticket, sit down and look up: The theater’s nifty ceiling features stars, clouds and tiny twinkling lights — it will make you feel like you’re outdoors on the Mediterranean at night. Drinking is encouraged: Bring beer or cocktails from the theater’s lounge into the movie with you (be a star and order the Douglas Fairbanks or Mary Pickford). You’ll sit there much easier knowing that Whitey, the ghost of the theater’s original manager, is watching over you.
David Podgurski has written about travel, books, fashion + entertainment for digital and print media. He’s hunted down vintage finds in crumbling attics, published poetry, worked for the New York MTA, and likes to haunt museums, cafés and shops. When he isn’t traveling or writing, he’s thinking about his next trip — and what to enjoy when he gets there.
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