Blair Kamin / Photo ' Chicago Tribune
Chicago Poetry Foundation / Photo ' Steve Hall/Hedrich Blessing
McCormick Tribune Campus Center / Photo ' Jeremy Atherton
Chicago Symphony Orchestra / Courtesy Jordan Fisher via Wikipedia
The Second City / Courtesy Gorilla Jones via Wikipedia
Blair Kamin is the Pulitzer Prize-winning architecture critic at the Chicago Tribune and author of Why Architecture Matters: Lessons from Chicago and Terror and Wonder: Architecture in a Tumultuous Age, both published by the University of Chicago Press.
Best Sustainable Sites
Jeanne Gang’s Aqua Tower (just north of Millennium Park); John Ronan’s Poetry Foundation Building (a few blocks west of North Michigan Avenue); and Millennium Park, whose grassy surface is actually one of the world’s largest green roofs. The park celebrates its 10th anniversary this summer.
Best Historic Architecture
An impossible choice due to Chicago's astonishing assortment of great buildings, but if forced to choose, I highly recommend that you see these three, all in close proximity in the Loop: the Hotel Burnham (the former Reliance Building), the Rookery Building, and the Sullivan Center (the former Carson Pirie Scott & Co. store). At the gateway to the Magnificent Mile, check out the newly-refurbished Wrigley Building. (A new Walgreens store opens at the Wrigley on June 25, just in time for the AIA convention.)
Best Off-the-Beaten Path Architecture
The Illinois Institute of Technology is a short ride (10-15 minutes) south of the Loop on the Chicago Transit Authority's Green Line. It offers an extraordinary cluster of buildings by Ludwig Mies van der Rohe, including the masterful Crown Hall, along with Rem Koolhaas's vibrant McCormick Tribune Campus Center, and Helmut Jahn's sleek State Street Village dormitory. A bonus is that the Green Line runs right through the stainless steel-sheathed, sound-baffling tube atop the campus center. Disney World has nothing like this. I also recommend a visit to the University of Chicago, which, in addition to its Collegiate Gothic core, has such distinguished new buildings as the Logan Center for the Arts by Tod Williams Billie Tsien. Get to the U. of C. by cab or Metra commuter rail’s South Shore Line.
Best Museums and Galleries
Visit the Art Institute of Chicago, especially Renzo Piano's Modern Wing and its modern and contemporary art. While you’re there, see the provocative Chicagoisms exhibition that crystallizes aspects of Chicago’s bold design past and charts new, if not altogether persuasive, directions for the city.
The best gallery of all is Chicago’s cityscape. A great way to take it in is the Chicago Architecture Foundation’s River Cruise.
Best Performing Arts
For performing arts, you can't go wrong with the Chicago Symphony Orchestra, the Steppenwolf Theatre Company, and the Second City Comedy Troupe. Also check listings for performances at the Frank Gehry-designed Jay Pritzker Pavilion in Millennium Park.
Best Dining, Drinking, and Shopping
Rather than give you a short list, here's a more extensive piece I wrote for Conde Nast Traveler's August, 2007 issue. It lists my favorite architecture tours, top-tier hotels, and restaurants that offer distinctive fare and a distinctive setting.
Two recent additions offer striking rooftop views of the downtown skyline: the Joe Valerio-designed Godfrey Hotel in River North; and the Wit hotel, by Jackie Koo, just outside the Loop.