Feature Image: October 2015. Chicago. 5.85mb DSCN1452 (1). Author’s photograph.

Chicago skyline from Museum Campus promontory (Northerly Island).

Wacker Drive and Wabash Avenue looking east, Chicago. From left: Trump International Hotel and Tower, Adrian Smith, architect (2009). Trump Tower Chicago is a 98-story skyscraper at 401 N Wabash Ave, completed in 2009. Rising 1,389 feet with its spire, it includes 486 condos, a 339-room hotel, and ranks as the 4th tallest building in the United States.

Wrigley Building, Graham, Anderson, Probst & White, architect (1921).

Tribune Tower (partially hidden), Howells & Hood, architect (1925).

401 N Michigan Avenue (Equitable Building), Skidmore, Owings & Merrill, architect (1965/Facelift 1992/Renovation 2016). The plaza (Pioneer Court) of the Miesian 401 N. Michigan draws over 22,000 pedestrians daily from busy Michigan Avenue. Apple’s global flagship store shares the plaza that provides immediate access to the Riverwalk via the Spanish Steps. see – 401 N Michigan Ave, Chicago, IL 60611 – Office for Lease | LoopNet – retrieved February 13, 2026.

360 N. Michigan Avenue (London Guarantee & Accident Building), Alfred S. Alschuler, architect (1923).

85 E. Wacker Drive (London House).

75 E. Wacker (formerly Lincoln Tower, originally Mather Tower), Herbert Hugh Riddle, architect (1928) and Harry Weese & Assocs. (Renovation/1983).

71 E. Wacker Drive (The Royal Sonesta Chicago Downtown, formerly Executive House Hotel), Milton Schwartz, architect (1959). 71 E. Wacker Drive is the first high-rise hotel in Chicago since the Great Depression. see – Executive House Hotel, 71 E. Wacker, Chicago – retrieved February 13, 2026.

Michigan Avenue and Van Buren Street looking west on Van Buren, Chicago. Left: Chicago Club, 81. E. Van Buren, Granger & Bollenbacher, architect (1929).

Right: CNA Center (333 S. Wabash Avenue), Graham, Anderson, Probst, architect (1972).

Near background: 333 S. State, DePaul Center (formerly Goldblatt’s, originally Rothschild & Co. Store), Holabird & Roche, architect (1912), renovation 1993.

Far background: Fisher Building (343 S. Dearborn Street), D.H. Burnham & Co., architect (1896) and Northern Addition, Peter J. Weber, architect (1907). Restoration and adaptive Reuse, 2001.

Adams and Dearborn Streets looking north along Dearborn, Chicago. Left: 55 Xerox Center, 55 West Monroe, Chicago, Helmut Jahn, architect (1977-1980). Behind (partially hidden): Chase Tower (originally First National Bank of Chicago), Perkins & Will; C.F. Murphy Assocs. (1969).

Right: 33 W. Monroe, Skidmore, Owings & Merrill, architects (1980). Behind: Inland Steel Building, 30 W. Monroe, Skidmore, Owings & Merrill, architects (1954-1958).

Background: 2 N. State/1 N. Dearborn Streets (originally, Boston Store), Holabird & Roche (1906; 1917), renovation (2001).

Halsted Street between Adams Street and Jackson Boulevard looking east, Chicago. Union Station Tower (MidAmerica Commodity Exchange), Skidmore, Owings & Merrill, architect (1971). Willis Tower (originally, Sears Tower), Skidmore, Owings & Merrill, architect (1974).

Balbo and Wabash Avenues looking north on Wabash. Left: (with Columbia College wall sign) 33 Ida B. Wells Drive building, Alfred S. Alschuler, architect, (1925/1926). DePaul University College of Law, 25 E. Jackson and, beyond, 230 S. Wabash, a 21-story building built in 1910.

Center: Trump International Hotel and Tower, Adrian Smith, architect (2009).

At right: Roosevelt University: Auditorium Building, Adler & Sullivan, architect (1887-1889) and The Wabash Building, a 32-story zigzagging glass structure, Christopher Groesbeck, AIA, architect (2012). CNA Center (333 S. Wabash Avenue), Graham, Anderson, Probst, architect (1972).

From left: Old Colony Building, 407 S. Dearborn Street, Holabird & Roche, architect (1894), Chicago Metropolitan Correctional Center, 71 W. Van Buren Street, Harry Weese & Associates (1975), Fisher Building, 342 S. Dearborn Street, D.H. Burnham, architect (1896) and Northern Addition, Peter Weber, architect (1907) and Sears Tower, 233 S. Wacker Drive, Skidmore, Owings & Merrill, architect (1974).

Lincoln Park looking over South Pond towards downtown. At left: (partial view) Water Tower Place, 845 N. Michigan Avenue, Loebl, Schlossman & Hackl, architect (1976); John Hancock Building, 875 N. Michigan Avenue, Skidmore, Owings & Merrill, architect (1969); 900 North Michigan Avenue, Kohn Pedersen Fox, architect (1989); Park Tower, 800 N. Michigan Avenue, Lucien LaGrange & Assoc., architect (2000); The Aon Center (formerly, Amoco Building; originally, Standard Oil Building), 200 E. Randolph Street, Edward Durell Stone; Perkins & Will, architects (1973); Trump International Hotel and Tower, Adrian Smith, architect (2009); At right: James House, 1560 North Sandburg Terrace, Solomon Cordwell Buenz, architect (1971).

Looking north on Wabash Avenue from Randolph Street, the Chicago elevated train follows a north-south route along Wabash Avenue and has been part of downtown since the late 1890’s. The “Kemper” sign is on the relatively dull modernist Kemper Building, now One East Wacker, Shaw, Metz & Assoc., architect (1962). Followed by 35 East Wacker Drive (formerly Pure Oil Building; originally, Jewelers Building) with its distinctive dome, Glaver & Dinkelberg; Thielbar & Fugard, Assoc. Archs., architect (1926). Partial view is Trump Tower. 

Right to left: The 233 E. Wacker Drive building (known as Columbus Plaza) in Chicago is 48-story apartment building, Fujikawa Conterato Lohan and Associates, architect (1978-1980).
The 111 E. Wacker Drive building (known as One Illinois Center) in Chicago, is a 30-story Modernist building featuring bronze anodized aluminum and dark-tinted glass, Ludwig Mies van der Rohe in association with Joseph Fujikawa, architect (1967-1970).
The Swissôtel Chicago at 323 E. Wacker Drive, is a 45-story, triangular, all-glass luxury hotel, Harry Weese and Associates, architect (1989).  
The 345 E. Wacker Drive building (known as Coast at Lakeshore East) in Chicago is a 40-story residential apartment tower, bKL Architecture LLC, architect (2013).

From the Riverwalk looking north along N. St. Clair Street: at right, the 27-story spandrel glass and metal panel 633 N. St Clair St. building, Loebl Schlossman [later; Dart] & Hackl, architect (1991).  
At left, the 63-story pinkish, rose-hued Swedish granite 161 Chicago Avenue East building (known as Olympia Centre) is a mixed-use retail, office, and residential skyscraper, Skidmore, Owings & Merrill, architect (1984-85).
At right, the 74-story gray marble facade Water Tower Place, the first vertical shopping center on Michigan Avenue (8 floors), also includes the Ritz-Carlton hotel, luxury condos, and office space, Edward D. Dart (Loebl Schlossman Bennett and Dart), architect (1975).
The John Hancock Center—now officially 875 North Michigan Avenue—is a 100‑story, tapered mixed‑use skyscraper known for its iconic X‑bracing. Often described as a “vertical city,” it is considered one of the first major mixed‑use skyscrapers in the world and includes office space (floors 13–41), about 700 condominiums (floors 44–92), and the highest indoor swimming pool in North America on the 44th floor. Its 94th‑floor observation deck offers panoramic views of Chicago and Lake Michigan. Bruce Graham of the firm Skidmore, Owings & Merrill, architect (1969). It was engineered by Fazlur Rahman Khan, who pioneered the tubular structural system used in the tower.

The Carbide and Carbon Building rises from 230 N. Michigan Avenue in Chicago like a gleaming Art Deco toast to the Jazz Age, Burnham Brothers, architect (1929). The 37‑story tower is instantly recognizable: its base wrapped in polished black granite, its shaft clad in deep green terra cotta, and its crown shimmering with 24‑karat gold leaf. Legend has it the architects shaped the building to resemble a champagne bottle — a fitting symbol for a city that never stopped celebrating its own ambition.

October 2015. Author’s photograph. 3.90mb.
Above: Alexander Calder’s Flamingo (1974) sits in Federal Plaza designed by modernist architect Mies Van Der Rohe. Behind it is Mies’ 45-floor John C. Kluczynski Building at 230 S. Dearborn Street and on a sunny east side of South Dearborn his 30-story Dirksen Federal Courthouse. Moving south across Jackson Boulevard is the 5-story 33 West Jackson Boulevard building built in 1910 (with additions/remodels stretching through 1917). Next to it is The Standard Club at 321 South Dearborn Street built in 1926 and designed by Albert Kahn. The Fisher Building (1896) at 343 South Dearborn Street and its annex is next further south. Designed by D.H. Burnham & Company, it was completed in 1896. The Old Colony building on the other side of the L tracks was built between 1893 and 1894, When it officially topped out, the 17-story, 215-foot high-rise briefly held the title of the tallest building in Chicago. It was designed by the legendary architectural firm of Holabird & Roche. The framework was engineered by Corydon T. Purdy who designed it with a highly advanced, pioneering skeletal steel-frame structure that carries the entirety of the building’s massive weight allowing the exterior features absolutely no self-supporting walls.

June 2022. Author’s photograph. 7.24 mb Above: On the west side of Clark Street between Adams Street and Jackson Boulevard—visible directly behind Alexander Calder’s Flamingo sculpture—the prominent structures are from left to right: The Commercial Office Building located at 118 South Clark Street (directly tucked between the Bankers Building and Jackson Boulevard)—was completed in 1920 and designed by the prolific Chicago architectural firm Holabird & Roche, Willis Tower in the distance, The Bankers Building (105 West Adams Street, completed in 1927 by the Burnham Brothers, a 476-foot Art Deco masterpiece featuring characteristic deep light courts and upper-tier setbacks), and, on the other side of Adams Street, The Field Building at 140 S. Clark. Completed in 1934 by Graham, Anderson, Probst & White, it stands as one of the finest premier masterpieces of Art Deco skyscraper design in the entire United States. A corner slice of the Edison Building is also pictured.