Chicago skyline guide

1 Willis Tower (Sears Tower), 233 S Wacker Dr. 1451 ft. The Sears Tower, long the tallest building in the world, today has to settle for second tallest in the Americas, as it trails the height of New York City's One World Trade Center by most (but not all!) measures. It was built for Sears, Roebuck, and Company in 1974 by Bruce Graham of Skidmore, Owings, and Merill. The innovative design successfully handled the challenges of air flow and elevator/emergency support for an unprecedented number of people, but the employees at Sears' formerly collegial suburban campus complained that it handled the challenges too well — they never saw anyone outside their own departments any more! Although Sears is no longer the primary tenant and the naming rights have been acquired by the Willis Group, the building remains home to several smaller firms. It is also known for housing Chicago’s most visited observation deck on the 103rd floor.

2 The Trump Tower, 401 N Wabash Ave. 1362 ft. The Trump Hotel and luxury residential building is the newest member of the Chicago skyline, completed at the beginning 2009, and the tallest after the Sears Tower—indeed, it is the fourth tallest in the United States. Trump intended for it to be the tallest in the world, but decided to scale back the plans to a mere "second tallest in North America" (after the Sears Tower) following the 9/11 terrorist attacks. The design features three prominent setbacks at the height of nearby buildings: the Wrigley Building, Marina City, and 330 N Wabash, which, combined with its singularly reflective exterior, allow this supertall to blend into the skyline, almost to the point where you could overlook it. As intended, the building reflects and interacts with the Chicago skyline, rather than imposing itself upon it with its great height. Regardless, you will not likely miss this building, and it's plenty interesting to examine — its asymmetric form ensures that you will see something quite different from any different vantage point. (updated Jan 2019)

3 Aon Center, 200 E Randolph St. 1136 ft. Originally known as the Standard Oil Building, The Aon Center is America's fifth tallest building from base to roof, and sixth by architectural detail. It was built by Standard Oil of Indiana in 1972 by architect Edward Stone. The building was later renamed the Amoco Building when Standard Oil of Indiana rebranded itself. The building was initially faced with marble, but the windy city began to blow the marble off the sides of the building—or so the legend goes. Actually, the Italian Carrara white marble slabs had undergone significant hysteresis as a result of the winter/summer seasonal changing temperature, and the marble was removed as a defensive measure to avoid potential liability from injury and damage if any of the slabs did fall. The entire building was refaced with granite, a costly job at around half of the original cost of the entire building! It is now named after its biggest tenant, the Aon Corporation, a risk management firm.

11 Park Tower, 800 N Michigan Ave. 844 ft. This very narrow skyscraper houses the Park Hyatt at the street level and luxury condos in the upper levels. It is one of the tallest buildings in the world that lack a steel frame, constructed of pre-cast concrete.

12 Aqua, 225 N Columbus Dr. 823 ft. The biggest American project ever to be headed by a woman, Jeanne Gang's skyscraper was named the world's best new building by Emporis when it opened in 2009 (four spots ahead of the Trump Tower across the river). Its most distinguishing feature is its series of undulating balconies, which extend as far as twelve feet from the building's walls, giving the building a surreal "rippling" effect. It uses an unforgettable curtain wall that compliments wavy balconies. Though impressive from any angle, it's best viewed relative to its "water" — either from a boat tour or the riverwalk over in the Near North.

13 Legacy Tower, 21-39 S Wabash. 822 ft. This very visible and hotly anticipated tower brought 360 new condos onto the downtown market, right in the heart of the Loop in 2009. Its immense height, its location looming above Millennium Park, and its striking, slender form have made this building one of the most visually arresting additions to the skyline throughout the 2000s construction boom.

14 Blue Cross Blue Shield Tower, 300 E Randolph. 797 ft. Originally a 33 story building, Chicago's health insurance colossus decided to expand towards the heavens, adding an extra 24 floors, up from 411 ft, to become one of the city's taller skyscrapers. The building was designed to allow for construction of additional floors, and was the first building to gain in height in city history.

15 300 N LaSalle. 785 ft. A major sustainable design project completed in 2009, extending the Chicago River's skyscraper canyon, and as an added bonus destroying a hideous riverfront parking garage.

16 Three First National Plaza, 70 W Madison St. 767 ft. This huge office building, just north of the Chase Tower, was built in 1981. Its nine-story atrium features Henry Moore's gigantic statue, Large Internal-External Upright Form. (updated Nov 2018)

17 Grant Thornton Tower (formerly Chicago Title & Trust Center), 161 N Clark St. 756 ft. This 1992 building's slanted roof is brightly illuminated at night.

18 One Museum Park, 1215 S Prairie Ave. 734 ft. One of the newest members of the Chicago skyline, and the tallest building in Chicago south of Van Buren St by far. It's the first real building on Grant Park's budding south wall, and serves as its soaring centerpiece.

21 Waldorf Astoria, 11 E Walton St. 686 ft. A thin skyscraper finished in 2010 on Chicago's Gold Coast, housing the Waldorf hotel, million+ dollar luxury condos (of course), and ground-level stores. It sports a faux-stone façade, a faux-French style roof, and general faux-taste.

22 111 S Wacker. 681 ft. Built in 2001, an attractive blue glass building. But the lobby is the most interesting sight, as its unique spiraling ceiling is actually the floor of the building's parking garage.

23 One Magnificent Mile (One Mag Mile), 980 N Michigan Ave. 673 ft. An odd bundle of four hexagonal tubes, each at different heights. Those heights were carefully chosen and placed to aid Oak Street Beach sunbathers by ensuring the buildings shadow would never shade the sand! (updated Nov 2018)

24 77 West Wacker (Previously the United Building and RR Donnelley Building), 77 W Wacker Dr. 662 ft. This 1992 building is one of Chicago's more attractive skyscrapers and has a classical theme to its design. Notable current tenants include the corporate headquarters of Archer Daniels Midland.

25 Daley Center, 55 W Washington St. 648 ft. The 1965 Daley Center is Chicago's principal civic center and boasts a gigantic Picasso statue on the adjacent plaza. A true Chicago landmark, the Daley Center was featured in The Blues Brothers, who drive across Daley Plaza and crash through the glass walls of the building. The Mies-esque design was intended to age visibly: the color has faded in a rust-like direction from exposure to the elements.

26 Lake Point Tower, 505 N Lake Shore Dr. 645 ft. This high-class, curvy residential tower stands by Navy Pier as the city's lone building east of Lake Shore Dr. It was built in 1968 by two students of Mies van der Rohe and has been home to some famous Chicagoans, including Sammy Sosa and Alice Cooper.

27 Leo Burnett Building, 35 W Wacker Dr. 635 ft. The RR Donnelly Building's neighbor, the Leo Burnett building is most notable for its rough textured exterior, and for the steel bars splitting its windows down the center. Built in 1989 for Leo Burnett Worldwide, a major advertising agency.

28 The Heritage, 130 N Garland Court. 631 ft. This 2005 arrival is a very successful office and residential building, owing to its favorable location just across the street from Millennium Park. Its distinctive convex and concave curves intentionally mirror those of Millenium Park's Pritzker Pavilion across the street. (updated Nov 2018)

32 Smurfit-Stone Building (Diamond Building or Crain Communication Building, after the new 2012 tenants), 150 N Michigan Ave. 582 ft. Anyone who has seen Adventures in Babysitting should immediately recognize this 1984 building, as its slanted roof (lit up at night) played a very important role in the film's climax. Although popular opinion holds that the building was intended as an, ahem, anti-phallic complement to Chicago's many masculine skyscrapers, the architectural firm who designed the building strenuously denies it.

33 Mid-Continental Plaza, 55 E Monroe St. 582 ft. Although not among the very tallest, this 1972 skyscraper is one of Chicago's (and the world's) most massive buildings. It has no setbacks and covers a full city block.

34 Onterie Center, 446 E Ontario St. 570 ft. Named after the two streets at its base, Ontario and Erie, the 1985 Onterie center features prominently the diagonal x-bracing structure, dedicated to the pioneer of that structure, Fazlur Khan, the structural engineer behind the John Hancock Center and Sears Tower. It is a mixed-use structure with retail, office, and residential space. (updated Nov 2018)

35 Chicago Temple Building. 568 ft. A skyscraper church; the tallest church building (but not the tallest church; see Ulm) in the world. Completed in 1924, it is home to the First United Methodist Church of Chicago. The first floor is occupied by a "sanctuary" two stories tall with seating for 1,000 people, but the really cool sanctuary is "Sky Sanctuary" at the base of the steeple (room for 30). Most floors house religious offices.

36 Palmolive Building (Playboy Building), 919 N Michigan Ave. 565 ft. This art deco Chicago landmark was built in 1929 for the Colgate-Palmolive Company, but became better known for its next tenant, the Playboy Company. The building really stands out on nights when its powerful beacon lights up the Chicago sky. Although previously sweeping a full circle, the beacon is now limited so as to not intrude upon the taller buildings around it. The building is being converted for residential use.

37 Kluczynski Federal Building, 219 S Dearborn St. 545 ft. This skyscraper was built in 1975, designed by Mies van der Rohe. The building is named for the Illinois 5th district congressman John Kluczynski, who served from 1951–1979. An adventurous (and oddly urban) raccoon may have set a raccoon world climbing record by reaching the scaffolding on the 36th floor in 2006.

38 Mather Tower, 75 E Wacker Dr. 521 ft. This 1928 building is instantly recognizable for its slim octagonal tower, which houses the smallest floors in Chicago. In 2000, the terra cotta crown began to fall off and was removed and subsequently replaced by helicopter.

After the events of September 11, 2001, it was proposed that the era of the super-tall skyscraper was over; people did not want to live or work in what were, essentially, big attack targets. Funding dried up for a while, and modest designs were the word of the day.

That didn't last long. Chicago is too wrapped up in the idea of the skyscraper to stop building them, and in time, the economic backing returned: Chicago's downtown underwent an unprecedented residential real estate and construction boom over the next six years, leading Forbes Magazine to declare the 60602 zip code the hottest in the country. Things slowed down following the financial collapse, but the air is still filled with cranes and scaffolding and dreams—expect the construction to pick up faster than the economy.

Real estate recovery no longer seems a matter of speculation as of 2013, with a range of new supertall constructions underway. Perhaps the most anticipated project of late is the set of three skyscrapers slated for construction on Wolf Point at the western bend of the Chicago River downtown, with the tallest reaching 950 ft. That will make for a busy section of town, given the construction of the 650 ft River Point just across the river!

46 OneEleven (Waterview Tower), 111 W Wacker Dr. 650 ft. This building was intended to open in 2009 to house luxury condos and the Shangri-La Hotel, slated to be Chicago's fifth tallest upon completion at 1047 ft. Such exciting plans have been deflated, though—in 2008, the project went on hold mid-construction, as there were financial problems related to turmoil in credit markets, and the proposed height was slashed nearly in half.