Ah, the Windy City. Chicago is one of the most fascinating cities in America—maybe even the world. But it’s often overlooked or derided simply because it resides in a “fly-over” state. That characterization is unfair and inaccurate; Chi-Town actually has a wealth of entertaining attractions well beyond the normal hullaballoo of Wrigley Field and the Sears Tower.
A trip to this jewel of the Midwest is highly recommended. Once there, visitors discover some of the best food, music, festivals and events that exist between the coasts. There’s so much more to find in this city and never enough hours to see it. Here are a few of the best off-the-beaten-track detours any and every visitor should take in. Hopefully this list will inspire travelers to search a bit beyond the concierge desk’s suggestions the next time they land at O’Hare.
SEE — The Cascade Drive-In Movie Theater
Definitely a fabulous option when visiting in cooler months (read: anytime besides summer), the Cascade offers a chance to step back in time. It’s a little out of the way—obviously this sojourn requires a rental car—but it’s more than worth the effort to enjoy an old school film experience at ridiculously antiquated prices. Plus, sneaking food into a movie was never easier, or more encouraged.
STAY — Ray’s Bucktown B&B Chicago
Sure, there are metric boat loads of glittering, modern high-rise hotels begging for visitors’ traveler’s checks. But why not experience something different, a place with character instead of cookie-cutter features? Ray’s has personality to spare, plus daily homemade breakfast from a menu of rotating items Ray makes himself. One other highlight of this unique Chicago mainstay: It has a sauna and steam room, which quickly warm away the chill of breezy days.
EAT — Andersonville Dinner Crawl
Naturally, everyone’s first instinct is to grub down on classic, deep-dish Chicago-style pizza. And they should; it’s amazing! But the Second City has so many tantalizing culinary opportunities available, especially ethnic options, so it’s folly to settle for just one genre. Thus, the Taste of Andersonville Dinner Crawl. Though it only happens once a year (this year it’s slated for August 7), brave culinary adventurers will enjoy three hours of sampling Chicago’s best eateries as chosen by locals. Plus, the dessert crawl happens immediately following the dinner run.
PLAY — Neo-Futurists
The intellectually stimulating arts and culture scene of Chicago is downright overwhelming. Yes, there’s the Museum of Contemporary Art and the Bank of America Theater, but the brains behind the Neo-Futurists delve a little deeper into legitimate independent artistic pursuits. Every performance is unique and—also an important consideration—affordable. Found in the same hip, young neighborhood as the dinner crawl, it’s ideally situated for an unforgettable night.
HEAR — The Hideout
The birthplace of jazz plays home to a broad variety of dulcet tones and a few cacophonous ones. The secret to hearing a great, live show in an intimate venue is to head to the outskirts of Noble Square and step inside The Hideout. The intriguing history of the 100-year-old establishment aside, the local bands and up-and-coming groups who play here give it their all, and the audience is never more than an arm’s length or two away from the action.
Ultimately, Chicago is a town of many faces. The popular Chicago attractions really are wonderful and worth visiting; they’re famous for a reason! But for those who have a little more time, an adventurous spirit or a need to try something different on this trip, these well-known secrets make for a truly remarkable—and non-touristy—Chicago experience.