The Loop, defined by the Chicago River to the west and north, Roosevelt Boulevard to the south and, of course, Lake Michigan to the east, is city’s commercial hub (roughly some 16,000 of Chicago’s nearly three million residents live here). It is the second largest central business district in the country, housing the world’s biggest commodities market.

The Loop initially took its name from the circuitous route 19th century streetcars took but later became defined by the elevated train tracks that lead here from every part of the city. The Center of the Loop, containing the financial district, is where Chicago’s reputation as the “Home of the Skyscraper” lies. The first tall building to be supported, both inside and outside, by a fireproof metal frame was built here in 1884. The oldest surviving skyscraper in the world is here. The tallest building in the United States has been here for almost 40 years. The skyscrapers came so fast and furious here that the building that lorded over the Chicago skyline for 35 years is now hard to see.

Our walking tour of the heart of the Loop will encounter many buildings with a “first” or an “oldest” or a “tallest” but before we descend into the great canyons of Chicago we will start in a treasured open space whose lakefront existence can be attributed to a single man...

Grant Park

Original plans drawn for Chicago called for the area between Michigan Avenue and Lake Michigan to remain undeveloped; in 1844 the town officially designated its “front yard” as Lake Park. In 1901 it would be renamed for Illinois native, triumphant Civil War general and 18th President of the United State, Ulysses S. Grant. By that time legal restrictions on building in the park were being routinely ignored and mail order pioneer Aaron Montgomery Ward personally financed four expensive court battles to rid Grant Park of its buildings and prevent the construction of new ones. The last twenty years of his life were spent preserving the Chicago waterfront as a park for the people. He spent over $200,000 of his own monies to defending the public’s right to open space. Ward’s long-time efforts to prevent the erection of buildings along Lake Michigan won him the title of “The Watch Dog of the Lake Front.” At one time there were 46 building projects planned in the park and he fought them all successfully, losing many influential friends along the way. Finally, just before his death in 1913 he won his final legal battle to forever keep the waterfront, as a sign posted here once stated: “Public ground. Forever to remain vacant of buildings.” The Chicago Tribune, no friend of Montgomery Ward, wrote, “We know now that Mr. Ward was right, was farsighted, was public spirited. That he was unjustly criticized as a selfish obstructionist or as a fanatic. Before he died, it is pleasant to think, Mr. Ward knew that the community had swung round to his side and was grateful for the service he had performed in spite of misunderstanding and injustice.” 


Monroe Building
104 South Michigan Avenue

Holabird & Riche, one of the town’s oldest and most prominent architectural firms, designed this unique pedimented skyscraper in 1912 as part of the street wall of Michigan Avenue. The Monroe Building became such a distinguished office location that the designers moved into the penthouse of the 16-story tower. Later, another architect occupied the top floor loft under the peak of the gable roof: Frank Lloyd Wright.

Municipal Courts Building
116 South Michigan Avenue

The slender three-bay tower at mid-block was constructed in 1905 by the firm of Jenney, Mundie & Jensen, the final major project for William Le Baron Jenney who introduced the skyscraper two decades earlier with the Home Insurance Building. The building was first used as a court space for the City of Chicago until a new City Hall was raised in 1911. The architects then came back and added more stories seamlessly in white terra cotta to raise the height to 16 stories.

Art Institute of Chicago
111 South Michigan Avenue

This is the one building that Montgomery Ward could not get removed from Grant Park. The Beaux Arts confection was designed by Shepley, Rutan and Coolidge of Boston, Massachusetts for the 1893 World’s Columbian Exposition as the World’s Congress Auxiliary Building with the intent that the Art Institute occupy the space after the fair closed. The Institute traces its beginnings to 1866 when 35 artists founded the Chicago Academy of Design. The iconic bronze lions at the Michigan Avenue entrance were carved by Edward L. Kenneys, an American sculptor known for his renderings of wild animals. If you walk around to the east entrance you can see the historic stone arch that marked the entrance to Louis Sullivan’s Chicago Stock Exchange from 1894.  When the Exchange was demolished in 1972 salvaged portions of the original trading room were brought to the Art Institute and reconstructed.

Peoples Gas Company Building
122 South Michigan Avenue

Daniel Burnham designed this burly building with more than a half-million square feet of office space in 1910 to match the ambitions of the Peoples Gas Company. The pillars at the base of the building are 26 feet tall and each one is crafted from a single piece of solid granite weighing 30 tons. Marble from quarries in Greece and 250,000 board feet of imported mahogany were used to fashion the interior. The classical flourishes of the facade include ornamental lions along the balustrade at the top.

Symphony Center
220 South Michigan Avenue

Daniel Burnham tapped the Neo-Georgian and Beaux Arts styles for this beautifully proportioned home for the Chicago Symphony Orchestra in 1904. Construction on the brick building trimmed out in stone was begun in May and the first performance took place in Orchestra Hall December, a disarmingly short time to create a National Historic Landmark, as the hall was designated in 1994, just prior to a $110 million facelift and expansion.

Santa Fe Building
224 South Michigan Avenue

The Atchison, Topeka and Santa Fe Railroad was organized single-handedly in 1859 by Cyrus K. Holliday and, through innovation and mergers, became the dominant carrier between Chicago and Los Angeles in the early 20th century. Its flagship passenger train was the immortal Super Chief, often referred to as “The Train of the Stars” because of the many celebrities who traveled on America’s first Diesel-powered streamliner. The Super Chief pioneered the iconic glass domes on its lounge cars and was the first all-Pullman sleeping car train in America. Along the way travelers could enjoy meals at the famous Harvey House restaurants strategically located throughout the system. The 17-story Santa Fe Building was designed by architectural luminary Daniel Burnham who was a major investor in the project and who moved his practice into a penthouse suite when the tower was completed in 1904. Standout features include bands of bay windows that climb the facade and the porthole windows along the cornice. The line’s “Santa Fe” logo sign still looks over the railroad tracks but all Santa Fe trains arrived and departed from Dearborn Station a few blocks away at Polk Street. The grand formal entrance is actually around the corner on Jackson Street, which was a more prominent street a century ago than Michigan Avenue.

Metropolitan Tower
310 South Michigan Avenue 

This was the first tower in Chicago to scamper up more than 30 floors when a city prohibition limiting buildings to 260 feet was abandoned in 1923. It was designed by the architectural firm Graham, Anderson, Probst & White as the headquarters of the investment firm S.W. Strauss & Co. The brawny 475-foot building is crowned by a 40-foot-tall pyramid and a blue beacon resembling a beehive. The beacon was intended as a symbol of the global reach of the financial men but came to be an apt landmark for the building’s most famous tenant - the Encyclopedia Britannica.

Karpen Building
318 South Michigan Avenue

Solomon Karpen, the eldest of nine brothers in a family that emigrated from Prussia in 1872, founded S. Karpen & Bros. Furniture in in 1880. Combining European craftmanship with innovative American marketing practices, the Karpen brothers quickly built the largest upholstered furniture company in the world. When they weren’t peddling divans and chairs, the brothers formed one of Chicago’s most famous family baseball teams in the 1890s. This six-story stone building began life in 1885 as the opulent Richelieu Hotel, credited with bringing fine dining to Chicago. Even so, it never made money. The Karpens fixed the building up as a factory in 1895. They would move on to more spacious digs sic blocks south in 1911.

McCormick Building
332 South Michigan Avenue

Cyrus Hall McCormick hailed from a farm in Rockbridge County, north of Lexington, Virginia. While still in his teens Cyrus, who was born three days after Abraham Lincoln in 1809, joined the family crusade to develop a mechanical reaper. His father had spent nearly 30 years working on a horse-drawn harvesting machine and obtained several patents but could never develop a reliable and marketable reaper. Cyrus received a patent for his version of a mechanical reaper in 1834 but would not sell one for another six years. Orders dribbled in for the next few years with all machines constructed by hand in the family farm shop. Finally McCormick received a second patent in 1845 for improvements and two years later moved to Chicago with his brother Leander to lay the seeds for what would become the International Harvester Company in 1902. The MCormick Reaper would yield one of America’s great fortunes of the 19th century and that money would manifest itself in Chicago for generations. Leander’s son Robert Hall McCormick used his share to invest in Loop commercial real estate and this was his headquarters, completed in 1910 on plans drawn by Holabird & Roche. It was originally much narrower, only 5 bays (10 windows if you are counting) and an additional four bays were added to the north later. If you look closely you can see the location of the original northern wall.  

The Chicago Club
81 East Van Buren Street at Michigan Avenue

The business and social club had its inception in 1861 in Chicago’s first business club known as the Dearborn Club. After a peripatetic first few decades the club moved into a handsome Daniel Burnham-designed building on this corner in 1893. Designed for the Art Institute, the distinguished structure was recognized as “the Gem of the Avenue.” During a make-over in the 1920s the building collapsed. Architects Alfred H. Granger and John C. Bollenbacher executed a re-design, salvaging the glorious Richardsonian Romanesque entrance that once graced Michigan Avenue and repositioned it on Van Buren.

The Studebaker Building
410 South Michigan Avenue

Five Studebaker brothers learned the family trade of wagonmaking in Ohio. Clement and Henry, the eldest, moved on to South Bend, Indiana to manufacture freight wagons but the real family money was first made by John who was making wheelbarrows in Placerville, California at the time of the great Gold Rush of 1849. Orders from the Union Army during the Civil War sent the fortunes of the Studebakers soaring and by the time of the great Western migration in the next decade half of the wagons on the trail were Studebakers. In 1875 the Studebaker Corporation, with all five brothers involved, was the “largest vehicle house in the world” churning out sulkies, broughams, phaetons, runabouts, and tandems. In 1885 the Studebakers set up a showroom and sales offices behind the over-sized arches of this building designed by Solon Spencer Beman. The two granite columns at the main entrance were said to be the largest polished monolithic shafts in the country. Today, known as the Fine Arts Building, it serves the needs of artists, musicians and dancers.

The Auditorium Building
430 South Michigan Avenue

Ferdinand Peck’s father Phillip came from Rhode Island to Chicago in the 1830s and made one of the town’s earliest fortunes in real estate. The younger Peck used his wealth mostly for civic causes - he was a founding member of the Illinois Humane Society and busied himself with bringing high art to the masses. In 1885 Peck organized the Chicago Grand Opera Festival that whetted his appetite to create the world’s largest, grandest and most expensive theater. Peck hired celebrated architects Dankmar Adler and Louis Sullivan to make his vision a reality. Adler’s engineering skills and Sullivan’s design savvy concocted the tallest building in the city and the largest in the United States. President Grover Cleveland laid the cornerstone for the Auditorium Building and Benjamin Harrison began his march to the White House when the 1888 Republican National Convention was held in a partially finished building. Today the building stands as one of the finest extant designs of Adler and Sullivan, since 1947 it has been the home of Roosevelt University.

Congress Plaza
Grant Park at Congress Avenue

In Daniel’s Burnham and Edward H. Bennett’s 1908 Plan of Chicago they envisioned this as the city’s front door with a magnificent staircase and bodacious plaza leading to the Buckingham Fountain and beyond that the Field Museum of Natural History. When Montgomery Ward successfully got buildings banned from Grant Park, the museum slid to the south, crippling the vision. The plan crumbled completely in the 1950s when the stairway was demolished to make room for the lakeside highways. The two statues standing here are the Bowman and the Spearman by Ivan Mestrovic; the works date to 1928.


Buckingham Fountain
Congress Parkway and Columbus Drive

The Buckingham family was instrumental in building southeastern Ohio around Zanesville in the early 1800s. Ebenezer Buckingham then brought his family to Chicago in the 1850s and became involved in grain and railroads. Son Clarence used lessons learned in the family business to build a fortune in banking and the Northwestern Elevated railroad company. Buckingham was an art enthusiast who took a stint as director of the Art Institute and much of his money, which continued to be dispersed by his sister Kate after his death in 1913, went to building the collection. Kate also put aside a million dollars for this fountain that was modeled after the Latonia fountain of Versailles, France. Edward H. Bennett designed the fountain in Georgia pink marble with four sea horses to symbolize the states that border Lake Michigan. The water jets, currently 193 of them, for one of the largest fountains in the world were turned on for the first time in 1927. Buckingham Fountain is the eastern terminus of America’s most famous highway, Route 66, the Mother Road - 2,451 miles later it ends at the Santa Monica Pier of the Pacific Ocean.


The Congress Hotel
520 South Michigan Avenue at Congres Avenue

Clinton J. Warren carved a reputation in Chicago in a four-year span from 1889 to 1893 when he designed the Congress Hotel, the Leander McCormick Apartments, the Metropole Hotel, the Plaza Hotel, and the Lexington Hotel. Only the Congress still stands. The larger Annex to the south came along in 1958.

Congress-Wabash Building
33 East Congress Parkway

Alfred S. Alschuler, whose crowning achievement would be the Chicago Mercantile Exchange in 1927, designed this seven-story brick and terra cotta structure a year earlier for Ferdinand W. Peck, Jr. It initially housed a bank, offices, and recreation rooms that included dozens of pool tables. A national billiards championship was contested here in 1938. It is now owned by Columbia College, founded in 1890 and one of the largest art colleges in the United States.

Second Leiter Building
401 South State Street at Congress Parkway

Levi Leiter began his Chicago business career in 1853 as a bookkeeper at Cooley, Wadsworth & Company, then the town’s leading retailer. He became a partner in the firm along with a fellow employee, Marshall Field. The two would go into business together until 1881 when Leiter cashed out and began investing his time and fortune in Chicago real estate. The First Leiter Building was designed by high-rise pioneer William Le Baron Jenney in 1879 and stood until it was demolished in 1972. The Second Leiter Building, another creation of Jenney, came along ten years later and is one of the earliest commercial buildings constructed with a metal skeleton frame remaining in the United States. Faced in pink granite, this was the flagship store of Sears, Roebuck and Company for over 50 years, beginning in 1932.

Harold Washington Library Center
400 South State Street at Congress Parkway

Sited in a virtual museum of historic skyscrapers, architects Hammond, Beeby and Babka adapted classical 19th century designs for this 1980s red brick-and-granite structure. The roof was accented with seven painted aluminum ornaments symbolizing the owl, the Greek symbol of knowledge. Since its opening in 1991 the block-filling library has appeared in the Guinness Book of Records as the largest public library building in the world.


Manhattan Building
431 South Dearborn Street

This heritage skyscraper was constructed between 1889 and 1891 and is the oldest surviving building in the world to use a purely skeletal supporting structure. Architect William LeBaron used projecting bay windows as a device to bring more natural light into the building.

Old Colony Building
407 South Dearborn Street

The “Old Colony” was the Plymouth Colony - this landmark building was developed by a Boston lawyer. The Plymouth Colony seal is reproduced in stone on the pillars flanking the Dearborn Street entrance. Holabird & Roche designed the 17-story tower to be constructed with arched portal bracing, the first skyscraper ever to employ the technique used in stabilizing bridges. Built with cream-colored Roman brick laid on a base of Bedford limestone, Old Colony features rounded bay windows at each corner.

Fisher Building
343 South Dearborn Street

There is no building in Chicago this tall that is older than the Fisher Building. Lucius George Fisher, Jr. was born in Wisconsin in 1843 and was about to enter Beloit College when gold fever erupted in Pikes Peak, Colorado. Fisher convinced his father to send him west to establish a quartz mill so across the Plains he went with a wagon and six yoke of oxen. During the Civil War he spent time in Sheridan’s campaign in the Shenandoah Valley of Virginia. After his discharge Fisher wound up in Chicago with the Rock River Paper Company, which he was put in charge of in 1870. By the time he commissioned D.H. Burnham & Company to create this building in 1896, Fisher’s Union Bag & Paper Company was the world’s largest manufacturer of paper bags. Charles Atwood in the Burnham office provided the design for the 18-story tower and laced the facade with terra-cotta carvings of fish, crabs, eagles and dragons. A few generations down the Fisher family tree came actress Jodie Foster in 1962.    


Monadnock Building
53 West Jackson Boulevard

A monadnock is a geologic term for a hill that stands alone and dominates the surrounding landscape, which this building certainly was when the 17-story structure was completed by Burnham & Root in 1891. There were tall buildings before this one but the Monadnock is where the term “skyscraper” entered common usage. There are two similar but stylistically different halves to the building; the north half was acclaimed as the best work of John Wellborn Root and it turned out to be his last as he died suddenly in early 1891 of pneumonia at the age of 41. Root eschewed all exterior ornament for his design, helping to usher in modern architecture where the beauty was in the form. He also supported half of the building entirely with a steel frame, which became the norm for tall buildings. Prior to that most buildings, including the northern half of this one, were supported by beefy masonry walls. One of the tallest brick structures ever executed, the north end required ground-level walls six feet thick. The north half of the Monadnock also displays the three-part ornamentation of traditional high-rises. The Monadnock was designed so that it could operate as four separate office buildings.  Each section stands on its own lot, and at one time each section had its own entrance, elevators, heating system and name: from north to south, they were the Monadnock, the Kearsarge, the Katahdin, and the Wachusett, each the name of a Civil War Union navy ship and also the name of a mountain in the developers’ native New England.


Federal Center
230 South Dearborn Street

This block once housed a showy domed Beaux Arts federal courthouse designed by Henry Ives Cobb. Al Capone, who had evaded all other charges, was convicted of tax evasion in the building in 1931. In 1960 Congress authorized a new government complex to be built here and modern architectural maestro Ludwig Mies van der Rohe was brought in as chief designer. The first of two towers, now a courthouse named for longtime Illinois Senator Everett M. Dirksen, was completed in 1964 (to your right on the east side of Dearborn). Mies died before the taller of the two, the 42-story John C. Kluczynski Federal Building, named for a Congressman, was finished in 1974. Both towers are elevated on open colonnades at the plaza level and are considered masterworks of the International Style as realized in Mies’ “less is more” philosophy.


Bank of America Building (Continental Illinois National Bank)
230 South Clark Street at Jackson Boulevard

Since someone invented the sundial man told time based on the position of the sun. Until a meeting took place here on October 11, 1883 when the famous Grand Pacific Hotel. With the coming of the railroad in the mid-1800s it became possible to travel much faster than the sun moved and long-distance train schedules became impossible to manage with more than 100 local timetables. The railroad men who met here that autumn day broke the country into four more-or-less equal time zones, each one hour ahead, moving east to west. The Standard Time System was inaugurated by the railroads on November 18, 1883. Almost immediately the federal government and cities and states across the country jumped on board and it is still used today. This Neoclassical office building replaced the Grand Pacific in 1924 for the Continental Illinois National Bank. Architects Graham, Anderson, Probst & White took not of the surrounding buildings with Corinthian and Doric columns and gave this building a complimentary ground level porticoof massive fluted Ionic columns.

Chicago Board of Trade
141 West Jackson Boulevard

The Chicago Board of Trade opened for business in 1848 and has had a home at this location since 1885. The first building here, designed by William W. Boynington, sported a tower that was the first structure in Chicago to exceed 300 feet and was the city’s tallest building for ten years. Its replacement, a classic Art Deco confection by architects Holabird and Root, was the first building in Chicago to climb over 600 feet and was the town’s Sky King for 35 years. Today, even though it is situated at the near geographic center of the Loop and remains the gateway to the financial district, the monumental limestone building is almost hard to see. Find the right angle and look up to see Ceres, the Roman Goddess of Agriculture surveying the goings-on from the point of a copper pyramid. The statue is made of three tons of solid aluminum.

Insurance Exchange Building
175 West Jackson Boulevard

At one time there were more insurance companies in this building than any other in the world. The 310-foot Neoclassical tower was constructed in two stages; the north half in 1912 and the south half in 1928. An Ionic portico lines the street level and another is along the upper stories. The 22-story structure was designed to support another 20 stories but they were never built - twice as many insurance agents could have been here.

Brooks Building
223 West Jackson Boulevard

Boston developers Peter and Shepard Brooks were active players in building ever upward in Chicago. Here the go-to-skyscraper architects Holabird & Roche designed a classic Chicago-style structure in the image of a Greek column with a defined base, standardized windows and   ornamental cornice at the top. A century on the 1910 building still radiates with brownish and green terra cotta detailing. 

311 South Wacker Drive
311 South Wacker Drive at Jackson Boulevard

Sitting atop this 961-foot tower, finished in 1990, are four smallish cylinders surrounding a large central barrel. More than 1,500 florescent tubes illuminate the cylinders producing a light so bright it is shut down at midnight so as not to be obnoxious. The odd rooftop conformation has given rise to a host of nicknames for 311 South Wacker Drive: “The White Castle Building,” “The Wedding Cake Building,” or “The Bart Simpson Building.” The cylinder are actually a very large representation of the engagement ring given by the architect to his wife. 


The Willis Tower
233 South Wacker Drive

The history of the country’s tallest building began with a shipment of refused pocket watches. Richard Sears was 15 when he became the family breadwinner in 1879. He worked in the offices of the Minneapolis-St. Louis Railroad but pestered his bosses for a field job. They sent him to North Redwood, Minnesota as a freight agent. Checking shipments in the station everyday Sears quickly learned about the mail order business. In 1886 a town jeweler refused a shipment of “yellow watches.” The Chicago commission house handling the watches wired Sears that as the station agent he could have the watches for $12 each rather then incur the return shipping costs. Sears knew the popular gold pocket watches were fetching $25 in retail stores. But he wasn’t interested in retailing. He took the watches and sold them to local station agents down the line for $14 each. Anything they made over that they could keep. Sears was hooked. As a bonded freight agent he did not have to pay to take delivery. He could settle his account when other agents paid him. It was a venture without risk, only profit. Sears began ordering more watches C.O.D. In six months he had amassed more than $5,000, a substantial fortune in 1886. He moved to Minneapolis, the biggest city he knew, and founded the R.W. Sears Watch Company. He began advertising watches in the paper, unheard of at the time, and found he had a natural flair for the work. So many orders poured in he needed to move to Chicago to facilitate shipping in 1887. In April 1887 an advertisement appeared in the Chicago Daily News: “WANTED - Watchmaker with reference who can furnish tools. State age, experience and salary requirement.” A tall, lean man from Hammond, Indiana answered the ad. He presented Sears an example of his best work. Sears studied it closely for a moment and admitted, “I don’t know anything about watchmaking, but I presume this is good, otherwise you wouldn’t have submitted it to me.” Alvah Curtis Roebuck was hired. Sears continued to build his business by undercutting the competition in price, often buying discontinued lines from suppliers. With low prices come suspicions of quality. Sears quelled such doubts with the strongest guarantees in the business. The business was always buoyed by its pledge: We Guarantee Satisfaction and Safe Delivery on Everything You Order. The story circulated through the Midwest of a customer who had come to Richard Sears with a crusty, bruised watch he had dropped on a rock in the mud. Sears handed him a new watch. When the customer protested that the damage was his own fault Sears stopped him, “We guarantee our watches not to fall out of people’s pockets and bounce in the mud.” Sears & Roebuck would one day have the most stores and the most customers in America. The company was the biggest publisher in the country. They shipped enough catalogs to fill a train of boxcars 30 miles long. One out approximately every 200 American workers worked for Sears. Sears alone accounted for 1% of the American Gross National Product. In 1969 when the company decided to consolidate all its employees around Chicago into a single building on the western edge of the Loop it would require the tallest building in the world. Well, not quite, but the plan was to rent out that extra office until the company’s expected growth would fill them up. Skidmore, Owings and Merrill LLP, an architectural and engineering firm that was formed in Chicago in 1936 by Louis Skidmore and Nathaniel Owings, built the grandest tower in the city using an innovative construction method of ever-longer bundled tubes. The height to the roof is 1,450 feet, the height to the top of the taller of two antennas is 1,729 feet. The tower is clad in black anodized aluminum. Since its completion in 1974, the building has fared better than the company. Not only did the expected Sears expansion not occur, the company tumbled so far down the retail food chain that it surrendered naming rights to the tower in 2003 and shuffled its employees off to smaller, more appropriate digs. The tower remained the world’s tallest building for over twenty years and remains America’s tallest skyscraper. Perhaps more amazingly it has lorded over the Chicago skyscraper jungle unchallenged for over 36 years - longer than any of the many other buildings that have held that honor in town ever did. 


Continental National Bank Building
208 South LaSalle Street

 Originally designed by D.H. Burnham and Co. in 1911 for the Continental National Bank, this adaptive reuse of a banking complex has been converted to a J.W. Marriott Hotel. The grand entrance features a three-story glass curtain behind fluted Doric columns. The name that adorns the tower is that of the succeeding institution to Continental, City National Bank & Trust. The chairman of City National from 1932 until 1951 was Charles G. Dawes, a descendent of William Dawes who rode with Paul Revere at the dawn of the American Revolution and who interrupted a finance career for public service. Dawes was awarded the Nobel Peace Prize for his program to re-stabilize Germany after World War I (it proved unworkable in practice) and served a contentious Vice-Presidency under Calvin Coolidge from 1924 until 1928. A self-taught pianist and composer, one of his pieces from 1912 was transformed into the chart-topping pop hit “It’s All In The Game” in 1958 by Tommy Edwards.


Bank of America Building
135 South LaSalle Street

For 45 years the world’s first skyscraper, the Home Insurance Company Building created by engineer/architect William LeBaron Jenney in 1884, stood here in anonymity. It was only when it was torn down to make room for this tower that its steel skeleton was discovered and it was anointed the distinction of “first skyscraper.” Even though construction for this 535-foot Art Deco tower began in the height of the Great Depression, its developers, heirs to the Marshall Field trust, had big plans to make this the biggest office building in the Loop. As it was, the Depression hit Chicago hard and there would not be another major building raised in town after this one for more than 20 years.


The Rookery
209 South LaSalle Street at Adams Street 

Built in 1887-1888, the Rookery is considered to be the oldest skyscraper standing in the world. Crafted of red marble, terra cotta and brick it is also considered on the masterpiece buildings of architects John Wellborn Root and Daniel Burnham. The architects combined iron framing with masonry bearing walls, marking a transition to modern high-rise construction. Its elegant appearance is a blend of Romanesque Revival and Victorian Queen Anne influences. While most of its contemporaries have been cleared out of the Loop for ever more modern high-rises, the Rookery managed to persevere through renovations. The first came in 1905 at the hands of Frank Lloyd Wright who remade the lobby, substituting contemporary white carved Carrara marble for the original wrought iron fixtures. The unusual building name comes from the crows and pigeons that swarmed over the previous structure on the site, an old town hall. Some wags have suggested, however, that the name comes from the dealings of the old building’s human inhabitants, not the avian ones.

Bankers Building
105 West Adams Street

Designed by Daniel Burnham’s sons and constructed in 1927, the Bankers Building is the tallest building, 476 feet, to be clad in bricks continuously from bottom to top. The architects designed a much more elaborate Gothic-flavored confection but plans were scaled back and the classical ornamentation is relatively sparse here.

United States Post Office - Loop Station
211 South Clark Street at Adams Street

The configuration for the Federal Center called for two towers, one of which would contain the United States Post Office. But the need for a street-level loading dock and the buzz of mail delivery trucks coming and going would have clogged the open plaza between the buildings so architect Ludwig Mies van der Rohe designed a separate post office with a below-grade access. Far from a throw-away, the single-story glass box post office instead evokes the guiding principles of Mies’ “skin and bones architecture.” The exterior of the building, like its fellow towers, is painted with flat black graphite paintto allow the shiny metal elements to be seen; look inside to see the number of service windows that harken back to 1973 when this building was finished and the post office was a busy, crucial space. The 53-foot steel structure in the plaza, painted in a contrasting bright red, is by celebrated artist Alexander Calder and called Flamingo.

Consolidated Edison Building
61 West Adams Street

Chicago Edison generated its first power a block west of here in 1888. Soon there were some 30 companies cranking out electricity, competing for customers. By 1907 when Consolidated Edison formed and moved into this 20-story tower the count was down to too and six years later there was only Con-Ed. Today this classically-flavored tower now houses the offices of the Chicago Public Schools, which purchased the Daniel Burnham-designed building for $8 million in 1997. 

Marquette Building
140 South Dearborn Street at Adams Street

The building was named after Father Jacques Marquette, the first European settler in Chicago who wintered in the area in 1674-5 winter season and it was a pioneer in its own right, standing as an early example of the Chicago School of Architecture. Designed by Holabird & Roche, the Marquette was one of the first steel-framed skyscrapers when it was completed in 1895. The architects gave the building. The architects gave the building large glass windows on a grid and a central light court, features that would become standard for Chicago-style skyscrapers. At the entrance four bas relief panels chronicle Jacques Marquette’s expedition around the Great Lakes. This is another skyscraper financed by the Brooks Brothers of Boston who never bothered to travel to Chicago to see the buildings that went up on their dime.

The Berghoff
17 West Adams Street

Four German immigrant brothers began brewing Berghoff’s Beer in Fort Wayne, Indiana, in 1887. Herman Berghoff began peddling the family’s Dortmunder-style beer at the Chicago World’s Fair of 1893 and the positive response encouraged him to open a cafe in town in 1898. Beer was a nickel, the sandwiches were free. Berghoff’s would remain a family restaurant for 107 years, continuing even through the Prohibition era by offering a near-beer along the lines of root beer. After Prohibition was repealed in 1933, The Berghoff was issued Liquor License No. 1. In recent years the the cafe has been resurrected. 

Chapin and Gore Building
63 East Adams Street

In the early 1850s, Gardner Spring Chapin, a broker in mining stocks, met James Jefferson Gore, who was running freight overland to Nevada but down on his luck. Chapin loaned Gore $200 to get to Nevada and a lifelong friendship was forged. The two went their separate ways but by 1865 they were in business together at the corner of State and Monroe streets, running a grocery store. Liquor was their biggest seller and soon Chapin and Gore were distilling their own bourbon in brands like “1867,” “Chapin & Gore Sour Mash,” and “Old Jim Gore.” The bourbon gained world renown as the company bounced around Chicago until 1904 when they moved into their own building here that combined a warehouse and office space with a street level retail store and bar. The design by Hugh M. G. Garden and Richard Schmidt is a paragon of the Chicago style emphasizing form over function. The building did have its decorative flourishes - ornamental capitals and cornice were removed in the 1950s. Today the Chapin and Gore Building is part of the Chicago Symphony Orchestra complex.