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Other than a couple of former sandbars, Chicago is flat, flat, flat.  Even when we raised the city out of the muck in the 19th century, it was basically just to a higher level of flat. 
The Roosevelt Road viaduct is another example of Chicago's man-made levels.  It goes on for blocks, towering above Dearborn Park, over once endless strands of railroad tracks now mostly gone, and on to the approach to the bridge over the Chicago River.

In the middle of that viaduct is The Roosevelt Collection, a mixed use development with 342 residential units and nearly 400,000 square feet of retail space, A. Epstein, RTKL and Hirsch Associates, architects.  While it has a new Target to the east, the complex, whose site plan looks like an oversized clothespin, otherwise lies within a moat of some of Chicago's largest tracts of undeveloped land.
The project, conceived by Centrum Properties, broke ground in 2007, the tail end of the condo bubble.  By the time things came on line after the crash, there was so little interest in the condos that existing contracts were torn up and the units converted to rental.  And while those apartments are reportedly now fully leased, the retail component, tther than a huge Icon movie multiplex, remains uncontaminated by tenants to this day.  In 2010, Centrum put the whole thing up for sale, and last year it was acquired by a joint ventured headed by McCaffery Interests for less than half the $350 million it cost to build. 
Since then, McCaffery has moved quickly,  with a new marketing campaign for what is now named The Lofts at Roosevelt Collection.  McCaffrey turned to Antunovich Associates to restart the design.
A series of clunky, never-occupied retail buildings in the center were demolished to create a more open plaza, now nearing completion, with dramatically lit fountains dedicated earlier this month.  
Construction has been going on so long,  it's been memorialized by a couple of J. Seward Johnson sculptures of construction workers installed on the plaza.
Even after all this effort, however, the retail plaza is still eerily quiet.  When I was there last Friday, the only sound was the music from a workman's radio.  Despite of flurry of speculation this past spring over prospective tenants - including everything from Lulelemon to Ulta to an Apple Store - the shopping center remains, as of today, a festival of emptiness.
The area around the Roosevelt Collection has always been a Bermuda Triangle of lost opportunity, centered around the massive corporeal ghost of former railyards that once served Chicago's great depots.  When Mayor J. Daley initially wanted to build a new campus for the University of Illinois there, he wanted it here, but was stymied by the prices the railroads, spinning towards bankruptcy, demanded for the land.  He wound up demolishing a large part of Chicago's Little Italy instead, for the UIC Circle campus.  It's taken nearly half a century for Little Italy to recover from the damage, and still the former railyards are empty.

The Roosevelt Collection is built on land that once held tracks leading into the old LaSalle Street Station.  The two blocks to the north remain vacant.
To the west, along Wells Street, the Roosevelt Collection shears off to another empty void, formerly holding the tracks leading to Solon Beman's masterful Grand Central Station, demolished in 1971.  In the center of this site, Bertrand Goldberg's River City was erected in the 1980s.  River City was originally to have been the capstone of Goldberg's career, a massively ambitious project on 230 acres with nine 72-story-high triad towers.  In terms of civic support, however, River City lost out to an alternate project, Dearborn Park, built beginning in the 1970's on 51 acres of formerly railyards formerly serving the decommissioned Dearborn Station.  The only part of the River City to be realized was the mid-rise element we see today.
The area along the river south of River City and next to the Roosevelt Collection remains vacant, as does the 11 acres north of River City, on the site of Grand Central Station.  In 2007, it was finally sold off by CSX - the successor corporation to the B&O Railroad - to a Skokie capital firm, but its highest use remains as an impromptu dog park.
The real prize, however, is to the south of Roosevelt  Road, 62 acres of former railyards that have reverted to a wonderous, semi-wilderness.
Rezmar Development had  big plans for the site - 4,600 residential units and 670,000 square feet of retail, centered on the first Ikea in the city's borders, but they were done in by the twin curses of the economic crash and the conviction and imprisonment of Rezmar's boodler/CEO Tony Rezko.  The site was put up for sale in 2010.  2nd ward alderman Robert Fioretti has suggested it as a location for the up-to-now mythical Chicago casino.  In 2010, the winning proposal in the Network Reset design competition co-sponsored by MAS Studio and the Chicago Architectural Club called for turning the 62 acres into parkland. Right now, however, it's just the land that time forgot.
As you can see, all of these parcels around the Roosevelt Viaduct  are below it.  McCaffery seems to sense the need for patching it all together, and has taken the unprecedented step of constructing a stair at the back of the Roosevelt Collection linking down to the lower level, although the only thing  there right now is a new dog park.
A multiple-level city is something Chicago encounters so infrequently that we don't do a very good job of it.  In terms of developing a visually compelling urban landscape, nothing beats breaking the flatness, whether it be the hills of San Francisco or the Spanish Steps in Rome.  The vistas created, and the contrasts they provide, can make a city both more comprehensible and more compelling.  You no longer seem lost in a grid that seems to just repeat, unto infinity.  You can see edges and borders, with well-designed stairways or inclines the markers of transition.  It brings a dense city back to human scale.
Right now, the Roosevelt viaduct is an anti-urban disconnect from the fabric of the city, just as the retail to the west of the river veers towards an anti-urban, shopping-within-a-sea-of-parking vibe.  Assuming all those vacant tracts around the Roosevelt viaduct eventually begin to fill up, the city needs something more than a development-by-development improvisation, lest the district become just a series of insular, self-contained mega-projects, existing in near-perfect isolation one to another. That's the profile of a second-rate suburb, not a great city.  All the parcels will be developed separately, but continuity counts.  Chicago needs a plan and a set of guidelines to stitch this tabula rasa together if the Roosevelt Viaduct District is to realize its potential as one the city's great neighborhoods
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