Free Unexpected Breathtaking Views of Chicago
by Peter Zelchenko August 21, 2009

Fine, technically these won't be unexpected if you go there and do them because I suggested it, so shoot me. But, forget The Bean and its $4.50 hotdogs, and forget grubbing onto some rich knucklehead's sailboat. There is plenty more to see here from the commonplace. Please send others if you have them and I'll broadcast them and credit you.

View of the skyline, from the flyover onto the Stevenson from the Dan Ryan. To do it right, you have to look behind you and risk causing a grisly accident, but it is probably the best unobstructed panoramic view there is that's not from a yacht, so it's well worth the threat of death and even a reckless homicide or two. This shot does not do it the least justice, but it should give an indication of the thrill of danger involved.

Watching the planes from either the Pulaski Orange Line stop or the Rosemont Red Line stop. You really have to be one station away from the airport to get the best effect of them making their turns toward the runways. This view actually costs a lot more these days, thanks to CTA's increasing fares, so get yours while it's still less than the Sears Skydeck. As a side trip, you can get off the Blue Line and ride back and forth along O'Hare's automated transport shuttles. There's nobody there to tell you it's the end of the line, so you could ride along for hours. And it's a lot cheaper and safer than actually flying somewhere.

Grant Park and down along the southern lakefront, from Dr. Symanski's ophthalmology office, 31st floor of the Prudential Building. Best advice would be to schedule an examination, and while wearing those funny temporary glasses gadgets ("trial frames"), ask to look through the window in the southern office to try to see the faint wisps of smoke coming from the power plants along the Michigan coast. I guess this view wouldn't actually be free at all, unless you were to skip out on the bill, which I don't recommend.

View from above of the northwest Loop El crossing, from at least the 3rd level of the parking garage on the southeast corner of Lake and Wells. As you stand there, think of the millions of working stiffs who have lurched through those crossroads morning and evening since the 1890s, lines under their eyes, confirmed resignation in their hellbent souls. Okay, perhaps it's not always that bad, but the somber view of creosote-soaked wood and iron says Chicago through to the bone, makes you want to play hookie from life.

Skyline view from the Orange Line overpass just southwest of the 35th and Archer station, as you cross over Pershing Road (39th Street). The tracks must soar about 100 feet into the sky. Funny that views from the Southwest Side are often the best, but that's where the least development has been done. After all, it doesn't take a 30-story skyscraper to do hogbutchering or even to destroy kids' lungs. This view is best enjoyed on the way to Bobak's, 5275 S. Archer, hard by the Pulaski station. Arguably the best all-around European Deli in the city for price, selection, quality, and, oh, its lunch buffet isn't the absolute worst, but little dives like Old Lviv and Staropolska beat it hands down and give you real plates, not styrofoam. But the meat selection kills Paulina Market and other upscale clipjoints.

Standing on the streets above Hubbard's Cave gives us one of our most commanding views of the grotto city. From the highest bridge, you can actually see several layers down into the city simultaneously, from the crossings above, to the train tracks, down to the poor suckers bumper-to-bumper far below. Incidentally, that last part is one of Chicago's worst experiences. A CBS-2 file photo -- shot from the bridge from which a poor soul leaped to his death in March -- also shows the network of streets further northward from which to get the best view down. My advice would be to look and not leap.

Another cavern view: from any subway grating. The many train tunnels underneath our city must be ventilated. There are frequent little electrical fires down there, and the various other subterranean gases are likely to kill us before they get to the rats. Listen carefully for these large gratings, available on many sidewalks, from which you can look down and see sometimes 50 feet or more into the cavern. Clybourn (Red Line) and Milwaukee (Blue Line) Avenues have some of the best ones, every block or so, although there are many downtown as well. Culturally very important in New York (think Marilyn Monroe's skirt, and freak accidents where people fall in), these are greatly undervalued in Chicago. At night, if you look carefully, you can actually see the lights from the train cars flitting past, glimmering the stagnant water so far below you. Ignore the passersby who laugh and ask how you're going to retrieve your quarter, or somesuch other sophomoric jab. You're seeing the real city here. You can also get the rat's-eye view of these tunnels, peering out from within the train with your coat over your head -- you're likely to earn yourself a few more sneers, but you will probably have the seat to yourself.

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