It’s easy to dismiss most of the Loop as being made up of bland, homogenized streets saturated with chain eateries and bizarre tourist retail-hives. But “easy” is for the lazy. Investigation is key, and hearty exploration into this area yields a satisfying dose of the brand of variety that makes Chicago so great.
Safety rating: There are generally enough people around during the day that the only safety concern is the traffic. At night, use good judgment.
Panhandler rating: Things are tough all over, and downtown Chicago is no exception. Expect many requests.
For the artiste
Chicago Cultural Center
Who knew? Not only is the Chicago Cultural Center an invigorating bouillabaisse of creative synergy, it’s also free. As you move through the doors, be sure to tilt your head back and soak in the 34-foot white marble archway, emblazoned with glass tesserae that spells out the names of the great thinkers of the antique world, heavies like Plato, Homer and Virgil. Even if this building were completely empty, it would still be worth a visit thanks to its stunning architecture; completed in 1897, it was dedicated the city’s first public library.
The acoustics are just as astonishing as the construction. Live classical music floods the center every Monday at 12:15 p.m. during the weekday LunchBreak concerts (held Monday-Friday with the exception of Thursday, when lectures and gallery talks are presented). Gallery-wise, architect-signed photographs of the Hedrich Blessing signature collection are currently on display, as is the three-dimensional work of Chicago-bred artist Roger Brown and an extensive collection of contemporary comic-book art. It should be noted that much of the comic art is adult themed, so bring the kids for that one only if you’re comfortable explaining STDs to them.
Also, look for the Art-O-Mat machine on the first floor. It’s a vintage cigarette vending machine converted to dispense packaged works of art at $5 a pop. Genius.
In-the-know spot
Filene's Basement
A huge discount on expensive designer clothes is the main draw to Filene’s subterranean department store. Aesthetically, the place is about as pleasing as a firebombed Montgomery Wards, but that’s not really the point. Snagging $200 designer jeans for $60 and enough discount Sean Jean, floppy-wear to wardrobe an entire nightclub is enough of a draw. You can also pick up inexpensive shoes, housewares, lingerie and kid’s clothes, all on the cheap.
Cheap eats
To Pho
It's not hot dogs or pizza, but for about the same price you can fill up on something a tad more eclectic. To Pho offers standard Vietnamese fare like grilled lemongrass beef and skewered pork tenderloin, and also serves chicken and tofu dishes. Naturally, they specialize in pho, a traditional Vietnamese soup that can be taken with every meal and is made with a broth that simmers for eight hours. Bahn Mi (sandwiches) and noodle salads round out the menu. Surrounded by all sorts of plants and bamboo, the outdoor patio is far more extensive and inviting than most in proximity. There’s nothing over eight dollars.
No wallet needed
Millennium Park
If you haven’t heard about this place, you must live in a vacuum. If you’ve heard but haven’t gone, you’re certainly missing out. A lot of time and money went into this trippy, sprawling park on the east side of Michigan Avenue. It can be thoroughly absorbed in under an hour, but puzzled over for quite a while afterward. Take the perplexing “bean,” a giant chrome-looking kidney that spectators can walk underneath, watching their reflections lurch and squish with each successive step.
Don’t forget the waterfall towers on your tour. On a temperate day, there will likely be hordes of children splashing about in the shallow puddle that collects between these two glass turrets, which display video images on their inner-walls. At roughly three stories, the towers offer a scaled-down and friendlier slice of “Blade Runner’s” L.A. skyline. The video on their opposing sides feature two gargantuan faces that blink and smile. Occasionally they will make an “o” face and spit ropes of water. Like I said, trippy.
Place to chill
The Palmer House Hilton
I can’t guarantee that the concierge will think this is a great idea, but why not grab a book and a thermos of coffee and hang out in the gorgeous lobby of the Palmer House. You’re afforded a high degree of anonymity in a hotel lobby. Even if you look a little out of place, the staff generally leaves you alone, as you could easily be a reactive guest. The Palmer House is North America’s oldest continuously operating hotel. In the belly of the hotel’s vestibule, that’s easy to believe. Gazing at the ceiling, it feels like you’re in Louis XIV’s parlor. If the book you bring grows dull, there’ll likely be about 50 intriguing people to study. In that way, hotel lobbies are like a giant ice cream social and mixer, minus the ice cream.
Place to be seen solo
Ada's Famous Deli and Restaurant
If you’re eating by yourself here, you won’t really be by yourself, at least not during the lunch rush. Whatever mayhem erupts late night at Ada’s fully stocked bar is the concern of those in town on business or pleasure. During the day, the sparsely decorated, sterile environment lends itself nicely to the smattering of lonesome diners gnawing away at decadent sandwiches. When was the last time you saw “Belt-Buster Burgers” on a menu? The food is delicious, and there’s a tub of pickles on every table, but this is one of those joints that makes you pay extra for French fries and calls it “deluxe.” The service is lackluster, so if you like being alone, rest assured you’ll probably be left that way.
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