“The methods we use for heating and cooling buildings are usually hidden in basements and not at all transparent. This is why I love Helmut Jahn’s design for the University of Chicago South Campus Chiller Plant (2010). The elegant glass box exposes the university’s ‘respiratory’ and ‘circulatory’ systems and even color codes them! And in some ways, the South Chiller Plant reminds me of a grain elevator—flowing with chilled water and steam, rather than corn—another type of kinetic structure that once dotted the Illinois prairie.” -- Jen Masengarb, Director of Interpretation and Research at the Chicago Architecture Foundation

“Everyone knows The Sears Tower (I mean Willis, of course) downtown—and rightly so—but far fewer are aware of a turn-of-the-century tower in the North Lawndale neighborhood that claims the title of Chicago's "original" Sears Tower. Sears, Roebuck & Co. was founded in 1893, and by 1906, had already solidified its presence as one of the country's largest companies by building a sprawling manufacturing complex on Chicago's West Side. Most of it is gone today, but a Homan Square community development plan aims to restore the handsome, neoclassical tower as a community center. Stop by to glimpse a bit of Chicago's middle-class, neighborhood-centric past—and maybe a bit of its future.” -- Chris Bentley, freelance journalist and Architects Newspaper editor

Designed by Benjamin H. Marshall and built in 1916, the since-demolished hotel (and still-standing apartments) represent a time when the city’s north side Edgewater neighborhood functioned as a mini resort town within the city’s borders (seaplane service used to take revelers from downtown to the area’s beaches). Before an extension of Lake Shore Drive isolated the complex and helped kill business, this pink palace was a place to be seen in the early 20th century; Charlie Chaplin stayed there, big bands led by the like of Benny Goodman regularly performed (and were broadcast by the hotel’s radio station) and guests drank at the nearby Yacht Club. Freelance architectural journalist Zach Mortice calls it the “pink cake-topper on the lake.”

"Amidst an otherwise typical neighborhood in the west side of Chicago stands the soft, billowing verticals of Presence Hospital. I know little about the history of this building but its physical mark on the neighborhood is unmistakable; the giant air intake arms that randomly dot the otherwise glass mid section. The tower that is seemingly held up with large fingers reaching down and gripping the underside. And sheer concrete corners that bring it all together. Forget the additions to the base; just look at those flowing corners." -- Brandon Biederman, Associate at PORT Urbanism

“For an architect associated with the low and the long, the Roloson Row Houses embody Frank Lloyd Wright's mastery of proportion, detail, and geometric form--in an unusually tall set of dense row houses. Beyond their form, they also tell a story. They were part of the reason he was fired from Louis Sullivan's firm (designing on the side).” -- John Morris, Chicago Patterns and Chicago Architecture Data

“This might be my favorite building in the city. Though the architecture demonstrates a mastery of the relationship of geometry in nature and built environment, it tells a dramatic story. A man I believe had the most important impact on American architecture, Louis Sullivan, was poor and destitute in his later years, and a former employee hired him to build this small music store.” -- John Morris, Chicago Patterns and Chicago Architecture Data

“My favorite oddball building is the Thompson Center. It's very dated looking and definitely not efficient whatsoever, but when you stand at the very base of the atrium and look up towards the ceiling, it does feel very encapsulating. It's a building that is decades old and feels kind of like a relic, but it still has this retro-futuristic feeling to it.” -- AJ LaTrace, Curbed Chicago Editor

“This housing complex, which looks like the city of the future circa 1968, was the result of architect Bertand Goldberg, perhaps best known for the corncob Marina City towers, putting his unique vision to work solving the problem of public housing. Many structures built for the same purpose espouse a utopian vision, but looking at the retro-future beauty of these buildings today, it’s hard not to feel optimistic.” Patrick Sisson, Curbed News Editor