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

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.