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 Loop has always been dominated by high-rises. The first tall building to be supported, both inside and outside, by a fireproof metal frame, the Home Insurance Building, was built here in 1884. Also the first high-rise to be torn down took place in the Loop - in the early 1900s when Marshall Field’s was expanding. The tallest building in the United States has been here for almost forty years.

Our walking tour of the northern end of the Loop will take in the theater district, the “cliffs” of Michigan Avenue, Chicago River, City Hall and more 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... 

1.
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.” The statue of Sitting Lincoln was created by celebrated Irish-born sculptor Augustus Saint-Gaudens in 1909 on the occasion of the 100th anniversary of the 16th President’s birth. 

TODAY THE NORTHWEST SECTION OF GRANT PARK IS OCCUPIED BY...

2.
Millennium Park

The railroad was the first to breech the dictum that the land east of Michigan Avenue remain undeveloped. The tracks were actually constructed on a causeway offshore but over time more and more land became filled in around the rail right of way, which became sunken. This space was part of the Illinois Central rail yards and after the City gained airspace rights over the tracks in 1997 a new civic park was conceived to fill 16 acres above a commuter rail station and parking garage, a project that would cost $150 million with the tab begin picked up by taxpayers and private donors. When the award-winning park opened in 2004 it was four years behind schedule, 50% larger than originally planned and over budget by $325 million. It boasts performance pavilions, interactive public art, gardens, an ice rink and more. By some measures Millennium Park is Chicago’s second most popular tourist attraction.

WALK OVER TO THE CORNER OF MONROE STREET, THAT SLICES THROUGH GRANT PARK, AND MICHIGAN AVENUE. TURN RIGHT AND BEGIN WALKING NORTH ON MICHIGAN AVENUE, THE LAKE IS ON YOUR RIGHT AS YOU WALK. STAY ON THE GRANT PARK SIDE OF MICHIGAN AVENUE.

3.
The University Club
76 East Monroe Street at Michigan Avenue

This has been called the world’s first Gothic skyscraper, designed by Martin Roche and completed in 1909. The price tag of over a million dollars was picked up the private University Club, formed in 1887 by graduates of mostly elite Eastern schools looking to extend their collegial experience. it was an age of luxurious private club buildings and this one had few peers. Over the years the University Club has played a prominent role in fostering the sport of squash in America.

4.
Gage Group
18,  24 and 30 South Michigan Avenue

This prime real estate was occupied in the 1890s by a trio of competing millinery businesses: Theodore Ascher and Company at #30 (the southernmost), Edson Keith and Company at #24 and the Gage Brothers and Company at #18. Today the most celebrated is the tallest, the Gage Brothers Building. The ornamental facade was designed by Louis Sullivan, the “father of the skyscraper” who helped usher in the creation of modern commercial architecture. One of only five Sullivan buildings still standing in Chicago, four additional stories were added to building in 1902 by different hands.

5.
Chicago Athletic Association
12 South Michigan Avenue

In the 1800s big city athletic clubs were a place where businessmen could exercise, enjoy an elegant meal and spend the night in convivial surroundings. It was common practice to erect palatial buildings to that end and this ornate 11-story Venetian Gothic structure was raised in 1890 when the Chicago Athletic Association was organized. The club formed the first quality football team in the city, in the years before Chicago came to be the dominant force in the sport.

6.
Willoughby Tower
8 South Michigan Avenue

Chicago’s first convent was constructed on this corner in 1846. This landmark tower was forced into its iconic form by a zoning mandate that decreed that once a tower reached a certain height any further construction could only be 25% as hefty. The limestone confection came online in 1929.

7.
Montgomery Ward Tower
6 North Michigan Avenue

Aaron Montgomery Ward was born in Chatham, New Jersey in 1844 and his family went west to Niles, Michigan in 1853 where his father took up the cobbler’s trade. Aaron left school at 14 to work in brickyards and a barrel factory and clerked at a shoe store and then a country store earning $6 a month -plus board. Ward was ready to go to the big city. In the 1850s Chicago was home to 30,000 people and known, none too affectionately, as “The Mudhole of the Prairies.” The streets were barely above the level of Lake Michigan and covered with bottomless goo. But by the late 1860s Chicago was teeming with post- Civil War energy. Fifteen railroad lines moved 150 trains a day out of the busy terminals. Like thousands of other young men Ward arrived in Chicago in 1866 and began work in various dry goods firms, including one operated by Marshall Field. He became a salesman, his income rising to the princely sum of $12 a week. While making his rounds Ward considered how he could help the disadvantaged farm and decided on a mail order store. His friends told him he would go broke trying to sell goods sight-unseen to backcountry folk. At first they were right by Ward persevered and he bound his first catalog in 1874 - it has since been chosen on many lists as one of the 100 most influential American books ever published. One such nominating committee, the Grolier Club, stated: “The mail order catalogue has been perhaps the greatest single influence in increasing the standard of American living. It brought the benefit of wholesale prices to city and hamlet, to the crossroads and prairie.” Ward erected this building, the tallest in Chicago at the time, in 1898, not only as a company headquarters but to put an impressive physical presence to his goods that were flowing facelessly through the United States mail. The building originally sported a ten-story rooftop tower, an 18-foot weather vane and an observation deck.

8.
Michigan Boulevard Building
30 North Michigan Avenue 

This 1914 Gothic-flavored high-rise stands as the northernmost brick anchor on Michigan Avenue’s famed architectural “cliff” running along Grant Park just across the Millennium Park. Look around the corner to see the building’s true form - a classic, two-story skyscraper with a light well running through the center. The building was originally only 15 stories but picked up six more in the early 1920s.

LOOMING BEHIND THE MICHIGAN BOULEVARD BUILDING ON WASHINGTON STREET IS...

9.
Pittsfield Building
55 East Washington Street

A 1923 zoning ordinance mandating setbacks for the tallest skyscrapers helped shape this 551-foot tower developed by the heirs of Marshall Field in 1927. The name is a tip of the fedora to the Berkshire Mountains town of Pittsfield, Massachusetts where Marshall Field obtained his first job and clerked for four years. After Field achieved unprecedented success in Chicago his first employer remarked, “Well, I’d never thought it of him. He was about the greenest looking lad I ever saw when he came to work for me.” Designed by Graham, Anderson, Probst and White, the structure combines both Art Deco and Gothic detailing.

CONTINUE ON MICHIGAN AVENUE.

10.
Chicago Cultural Center
78 East Washington Street at Michigan Avenue

After Henry Hobson Richardson, working out of Boston and the most influential American architect of the 1880s, died suddenly at the age of 47 in 1886 his practice was assumed by George Foster Shepley, Charles Hercules Rutan, and Charles Allerton Coolidge. For major commissions in Chicago and the World’s Columbian Exposition, Coolidge moved to Chicago and the firm opened its branch office there in 1893, winning a design competition for the city’s central library and Grand Army of the Republic Museum. The block-filling Italian Renaissance structure, faced in Bedford blue limestone, was completed in 1897 at a cost of nearly $2 million. The library moved on in 1991 and the City created the nation’s first free municipal cultural center, presenting more than 1,000 programs and exhibitions covering a wide range of the performing, visual and literary arts.  

TURN RIGHT ON RANDOLPH STREET. 

11.
Aon Center
200 East Randolph Street

This tower was designed as the headquarters for the Standard Oil Company of Indiana and when it was completed in 1973 it was the tallest building in Chicago and the fourth tallest in the world. Befitting it lofty stature, “Big Stan” was sheathed with 43,000 slabs of Italian Carrara marble, the same stone Michaelangelo worked with. Marble had never been used for so high a building before and the marble panels proved to be too thin and buckled and cracked within a year of the Standard Oil Building’s opening. Unsightly stainless steel straps were added to hold the marble in place but in the early 1990s all 5,900 tons of marble were removed and replaced with North Carolina granite. The cost was estimated at $60 million, more than half of the 1,147-foot high building’s original price tag. Most of the granite was crushed and hauled to an Amoco refinery in Whiting, Indiana but some just ended up as paperweights.

TURN LEFT ON NORTH COLUMBUS DRIVE.

12.
Aqua
225 North Columbus Drive

With Jeanne Gang at the lead of the design team, this 86-story mixed-use residential skyscraper is the tallest building in the world to have a woman as lead architect. The sculptured facade is created by undulating balconies of varying lengths to reproduce the Great Lakes topography. Some balconies are as wide as twelve feet, others just big enough to stand on. When it was finished in 2010 the 870-foot tower was the first residential building in Chicago to have a charging station for electric cars.

TURN LEFT ON WATER STREET AND MAKE YOUR WAY, PARTIALLY UNDERGROUND, BACK TO MICHIGAN AVENUE. WHEN YOU ARRIVE, IN FRONT OF YOU WILL BE...

13.
Carbide and Carbon Building
230 North Michigan Avenue

The Union Carbide and Carbon Corporation was formed in 1917 from the merger of the former Union Carbide founded in 1898 and the National Carbon Company founded in 1886. These companies made carbon rods for arc lights and electrodes for electric arc furnaces, and produced aluminum. Their 37-floor headquarters was constructed in 1929 on plans drawn by Daniel and Hubert Burnham, sons of skyscraping pioneer architect Daniel Burnham. The exterior of the building is covered in polished black granite, and the tower is dark green terra cotta that enabled its creators to claim it was the world’s first full-color skyscraper. If that wasn’t enough ornamentation the designers draped the tower and upper floors in 24-karat gold leaf - real gold 1/5000 of an inch thick. The gold accents drip all the way down the building’s facade. The look of the Carbide and Carbon Building was said to have been inspired by a green champagne bottle.

TURN RIGHT ON MICHIGAN AVENUE AND WALK UP TO THE CHICAGO RIVER.

14.
Michigan Avenue Bridge
Chicago River

Technically, the Michigan Avenue Bridge is a double-deck, double-leaf trunnion bascule bridge, the first of its kind ever built. Specifically, a bascule bridge is a drawbridge hinged with a counterweight that continuously balances the leaf throughout the entire upward swing in providing clearance for boat traffic. When it opened in 1920 it was considered a mechanical marvel and remains so today. Artistically, the walls of the four Beaux Arts bridgehouses are decorated with bas relief sculptures depicting important moments from Chicago history. Originally the bridge was staffed 24 hours a day, and opened up to 3000 times a year to allow ships through, but since the 1970s bridge lifting has been scheduled in the spring and autumn, when the bridge is raised twice weekly to allow sailboats to pass between Lake Michigan and inland boat yards where they are stored for the winter.

TURN RIGHT ON CONTI STREET.

15.
333 North Michigan Avenue 

This was the last of the four sentinels to rise over the Michigan Avenue Bridge, representing one of the most valuable patches of real estate in Chicago. A slight jog in Michigan Avenue insures the high visibility of this building plot. John Wellborn Root, Jr. based his long and narrow design on principles pioneered by his famous architect father and the runner-up design of Eliel Saarinen in the Tribune Tower design contest that introduced setbacks to high-rises. The architect was so pleased with the finished product that he and his partner William Holabird took commercial residence here. The building is embellished by a polished marble base and ornamental bands. 

ALSO ON THE CORNER, ACROSS THE STREET IS... 

16.
London Guarantee and Accident Building
360 North Michigan Avenue

A small fort was built on this site in 1803 beside the Chicago River - the first stirrings of what would become Chicago. It was constructed by troops under Captain John Whistler and named in honor of Henry Dearborn, then United States Secretary of War. Fort Dearborn was destroyed in the War of 1812 but re-constructed on the same site in 1816. The fort was de-commissioned by 1837, and parts of the fort were lost to the widening of the Chicago River in 1855 and a fire in 1857; the last vestiges being destroyed in the Great Chicago Fire of 1871. From 1872 until 1921 the Hoyt Building stood here and currently the birthplace of Chicago is occupied by this 342-foot trapezoidal tower, one of a squadron of sky-tickling sentinels around the Chicago River with distinctive tops. Here designer Alfred S. Alschuler provided a rooftop pavilion modeled after the Stockholm, Sweden’s town hall. Under a Roman-flavored doorway, the London Guarantee Building boasts a large relief above the entrance commemorating Fort Dearborn.

ACROSS THE CHICAGO RIVER, TO THE RIGHT OF THE MICHIGAN AVENUE BRIDGE, IS... 

17.
Tribune Tower
435 North Michigan Avenue

James Kelly, John E. Wheeler and Joseph K.C. Frost put out the first edition of the Chicago Tribune on June 10, 1847 but it was under the 20th century editorship of Colonel Robert R. McCormick that the Tribune became the self-styled “World’s Greatest Newspaper.” In 1922 McCormick hosted a $100,000 international design competition for “the most beautiful and eye-catching office building in the world.” Mostly a publicity stunt, the competition attracted 260 entries and indeed produced a memorable building from the $50,000 first prize winners Raymond Hood and John Mead Howells of New York. Their French Gothic skyscraper is a flurry of flying buttresses, spires, and grotesques. But the creation was an interpretation of the past; the most influential design would turn out to be the simplified tower with setbacks that anticipated the future submitted by runner-up Eliel Saarinen of Finland, who pocketed $20,000 for his efforts. Even before construction of the 462-foot tower began McCormick was instructing his Tribune correspondents to brick back stones and bricks from historically important sites from around the world. Today more than 150 such artifacts are incorporated into the base of the tower from places such as the Great Pyramids of Egypt, India’s Taj Mahal, the Great Wall of China, the Alamo in San Antonio and Old Swedes Church in Wilmington, Delaware.

ACROSS THE CHICAGO RIVER, TO THE LEFT OF THE MICHIGAN AVENUE BRIDGE, IS...

18.
The Wrigley Building
400-410 North Michigan Avenue

No one knows how William Wrigley became interested in chewing gum. Wrigley was the eldest of eight children born to a Philadelphia soapmaker in 1861. He had $32 and one carload of soap when he established William Wrigley Jr. and Company in Chicago in 1890. He ordered his first batch of gum in September 1892 as an inducement to buy his baking powder, which he had just added to his product line. Jobbers found they could sell the free gum better than the baking powder so Wrigley decided to sell chewing gum. His first product was the long-forgotten “Wrigley’s Vassar.” The gum was mixed like dough, rolled, cut into sticks and packed by hand. Wrigley changed the product by making chicle, a juicy extract from tropical trees, his main ingredient. Growth was slow. He began advertising with trademark arrows and elves and gradually his gum gained acceptance. On two occasions he collected the names of every telephone subscriber in Chicago and sent each a package of chewing gum.

TURN LEFT ON WACKER DRIVE AND WALK ALONG THE CHICAGO RIVER, WHICH WILL BE ON YOUR RIGHT.

19.
Mather Tower
75 East Wacker Drive

Alonzo Mather, a direct descendent of the influential 17th century New England minister Cotton Mather, pioneered a more humane stock car for the shipment of livestock by rail in the 1880s. When the railroads discovered it was cheaper to lease Mather’s boxcars than to build their own fleet, his fortune was assured. Mather’s business model was so successful his was one of America’s few companies that prospered during the Great Depression and carried him to his deathbed in 1941 at the age of 92 a very rich man. Mather commissioned Herbert Hugh Riddle to build him a new company headquarters but he remained active in its design. When Mather’s Neo-Gothic tower, clad in terra cotta, was completed in 1928 it was briefly the city’s tallest building at 521 feet high. The unusual configuration placed a 21-story octagonal tower atop a more familiar 20-story rectangular box. To this day the interior of the octagonal tower has the smallest floors of any skyscraper in downtown Chicago.

ACROSS THE RIVER, BEFORE THE WABASH AVENUE BRIDGE, IS...

20.
Trump Tower Chicago
401 North Wabash Street 

This building was planned as the world’s tallest in 2001 but after the terrorist attacks in New York City Donald Trump dialed down those lofty ambition. When it opened in 2008 it topped out at 1,389 feet, ranking it sixth or seventh, depending on various measuring criteria. Either way, it did boast the world’s highest residence above ground at the time. Trump Tower’s 98 stories rise on the historic location of the former Chicago Sun-Times Building; its setbacks and sensual aluminum-and-steel curves help battle the frisky Lake Michigan winds. Trump thrust the tower into the national spotlight when the winner of the first season of The Apprentice, Bill Rancic, was chosen to manage the construction of the tower.

21.
Jewelers’ Building
35 East Wacker

The ornate appearance of this domed Renaissance Revival tower from 1926, one of the last of its ilk in the coming era of stripped-down Art Deco classicism, masks some of its ingenious practicalities. The wildly decorative four corner turrets, for instance, hold cast iron water tanks that could be emptied in the event of a fire. The building was originally constructed for jewelry merchants and inside was a car elevator that enabled couriers with valuable stashes of jewels to be whisked directly to their upper floor offices without getting out of the car. By 1941 the car elevator was sacrificed for more revenue-producing office space.

ACROSS THE RIVER, AFTER STATE STREET, IS...

22.
Marina City
300 North State Street

These twin corn cob towers are credited with triggering the residential renaissance of American cities after they appeared in 1964, the first urban high-rise residential complex built in the United States after World War II. The $36 million price tag was picked up mostly by the International Union of Janitors who were trying to stem the flight to the suburbs of its members. When finished, the two towers were both the tallest residential buildings and the tallest reinforced concrete structures in the world. Marina City was exactly that - a city inside a building. On-site facilities included a theater, a gym, ice rink, bowling alley, stores, a restaurant and the marina. The bottom 19 floors form an exposed spiral parking ramp and a laundry room occupies the 20th floor; the residences are located above that. In their half-century of existence the towers have done star turns in countless Hollywood productions including the opening sequence of The Bob Newhart Show, The Dark Knight, Nothing In Common and more.    

ACROSS THE RIVER, BEFORE LASALLE STREET, IS...

23.
Reid, Murdoch & Co. Building
325 North LaSalle Drive

George Croll Nimmons was a Chicago architect best known for his work for Sears, Roebuck and Company, including a Kenwood mansion for Sears’ President, Julius Rosenwald. Here he designed a warehouse and office for grocers Reid, Murdoch & Company in 1914. the landmark clock tower was originally centered in the building but the proportions shifted when LaSalle Street was widened in 1926. The City of Chicago was a long-term tenant beginning in the 1950s and the Encyclopedia Britannica has been headquartered here.

24.
LaSalle-Wacker Building
221 North La Salle Street

This classic Art Deco tower, clad in limestone and granite, was originally planned as a 37-story building but when an adjacent site was purchased the final structure picked up a recessed center that filters light down into the office space. The 512-foot high-rise comes alive at night with colored illumination - the beacon on top of the roof was built to be seen from 200 miles away.

ACROSS THE RIVER, BEYOND WELLS STREET, IS...

25.
The Merchandise Mart
222 Merchandise Mart Plaza

Goods have been handled on this location from Chicago’s earliest days when a Native American trading post was here. The Chicago and North Western Railway had their main terminal here until 1911 after which retailer Marshall Field eyed the location on the north bank of the Chicago River for a single wholesale warehouse for the entire nation that would consolidate 13 warehouses. Construction on the “largest building in the world” began in 1928 on Art Deco plans drawnby the Chicago architectural firm of Graham, Anderson, Probst and White. With more than 4,000,000 square feet the Merchandise Mart kept the title until surpassed by the Pentagon - it had its own zip code until 2008. If you walk across the Wells Street Bridge you can see over-sized busts lining the river of merchants inducted into the Merchandise Mart Hall of Fame by Joseph Kennedy. The Kennedy family owned the building for over 50 years. 

TURN LEFT ON LASALLE STREET.

26.
The Cadillac Palace Theater
151 West Randolph Street at LaSalle Street

The Rapp Brothers, George and Cornelius, were the acknowledged leaders in theater architecture in America in the early decades of the 20th century, with a long list of sumptuous entertainment palaces around the country on their resume. Here, in their hometown, the Rapps adapted the look of the palace of Versailles in Paris in burgundy and beige, with gold leaf accents for the New Palace Theater in 1926. Atypically for the age, the Palace was designed only for live performances, no silent pictures or new “talkies” here (at least until 1931). This would be one of the final projects for the Rapp brothers - Cornelius would pass away in 1926. The current vertical marquee is the product of a recent renovation.

27.
City Hall
121 North LaSalle Street

This is the town’s fourth building to serve as City Hall, with more than a century of service since its completion in 1910. William Holabird and Martin Roche had worked in the office of William LeBaron Jenney before emerging on their own. The new firm became well-known for its groundbreaking Chicago School skyscrapers and here they tapped the Neoclassical style for the block-filling civic structure. Each of the fluted Corinthian columns that march around the exterior is 94 feet tall.

28.
Lumber Exchange Building
11 South LaSalle Street

Leander J. McCormick joined his older brother Cyrus in manufacturing mechanical reapers and becoming one of the wealthiest families in America. At the age 70 in 1889 Leander left the agricultural implement business behind and began buying up large swaths of downtown Chicago with his cash. This corner was one of his purchases, then housing a rambling seven-story structure called the Roanoke. In 1915 McCormick’s heirs hauled down the Roanoke, hired the go-to skyscraper designers William Holabird and Martin Roche, and signedup the Lumberman’s Exchange as major tenants. Holabird & Roche delivered a vertically ribbed 16-story tower with affectations described as Portugese Gothic to the facade. The confection came with a decorative crown but it was jettisoned when the tower grew another five stories in 1922. Another tower was added along Madison Street three years later.

29.
Central Y.M.C.A
19 South LaSalle Street

In 1858 a branch of the Young Men’s Christian Associations (YMCA) was constituted in Chicago, fourteen yeas after the birth of the organization in London in 1844. The YMCA moved into this facility in 1892, built by engineer and architect William Le Baron Jenney. The L-shaped design featured 54 feet fronting La Salle Street and 187 feet along the alley on the south side. Members could avail themselves of a bowling alley, swimming pool and gym. Today the building is a branch of the State Bank of India.

30.
The Northern Trust Company Building
50 South LaSalle Street

There was a time when all the buildings in the Loop were constructed on the same scale as this orange stone Beaux Arts vault constructed for the Northern Trust Company in 1905. Of course, a tower was planned for the top of the building but it was never constructed. Northern Trust was founded in 1889 by Byron Laflin Smith in a one-room office in the Rookery Building, planning to cater to Chicago’s elite. Smith provided 40% of the bank’s original capitalization of $1 million himself, while financial heavy hitters such as Marshall Field, Martin A. Ryerson, and Philip D. Armour were among the original 27 shareholders. 

TURN LEFT ON MONROE STREET.

31.
Chase Tower
10 South Dearborn Street

At 850 feet this is the tallest building inside the Chicago Loop elevated tracks, the official geographic boundary for the mythic “Loop.” It is the tenth tallest tower in Chicago. Completed in 1969 the Chase Tower rises from a sunken concrete Plaza that was the site of the First National Bank of Chicago, chartered in 1863 and located here since 1896. The tower’s distinctive curving northern and southern flanks serve a practical purpose - they provided needed retail banking space down low without sacrificing prestigious upper office space. Fans of National Public Radio will recognize Chase’s Auditorium as the taping location for the weekly news panel game Wait Wait...Don’t Tell Me!

32.
Inland Steel Building
30 West Monroe Street

The Great Depression slammed the brakes on development in Chicago and this was the first skyscraper to be constructed in the Loop in twenty years when it was started in 1956. Designed by Bruce Graham and Walter Netsch of the Skidmore, Owings & Merrill, the 332-foot tower is considered a landmark of modern architecture. The placement of all structural columns on the building’s perimeter―and the consolidation of elevators and other service functions in a separate tower―allowed for a highly flexible interior floor layout with no interior columns. The brushed stainless steel skin speaks to the original owner, Inland Steel Company, founded in 1893 and a specialist in manufacturing cold-rolled steel for motor vehicles. Inland Steel was acquired by international interest in 1997.

33.
The Majestic Building
22 West Monroe Street 

The main attraction of this 18-story tower when it opened in 1905 was its large vaudeville theater with seating for 2,000. Edmund R. Krause designed the Renaissance-flavored, four-bay building with richly ornamented white terra cotta.

TURN RIGHT ON STATE STREET AND WALK A FEW STEPS DOWN TO THE SKINNY BUILDING.

34.
Singer Building
120 South State Street

Isaac Merritt Singer was born in upstate New York in 1811. He ran away from his parents at age 12 to join a group of traveling actors. Singer remained an actor until he was 24. After that he worked as a machinist and acted on the side. For years his means were small and he despaired of ever inventing anything successful. Sewing machines had been available since 1790 but it was Isaac Singer who created a reliable machine with a straight needle that moved up and down. By the 1900s the Singer Manufacturing Company was synonymous with sewing machines. Singer’s retail presence on State Street began here in 1902 and in 1926 this 10-story store/office/warehouse was squeezed into this 25-foot wide lot. Despite the constricting circumstances Elmer C. Jensen was able to make an architectural statement with this Neo-Gothic thread executed in cream-colored terra cotta. Through serendipity this sliver of Chicago’s architectural heritage has survived the evolution of State Street around it.

RETRACE YOUR STEPS TO MONROE STREET.

35.
The Mentor Building
39 South State Street at Monroe Street

Architect Howard Van Doren Shaw, who was associated with many projects on the Gold Coast, dipped into Chicago’s retail hub to design this 17-story tower in 1906 the second Mentor Building to stand here since the Great Chicago Fire. Shaw would remain in practice another 20 years but he never again designed a building as tall as this one. 

TURN RIGHT ON MONROE STREET. AT WABASH STREET, TURN LEFT.

36.
Silversmith Hotel
10 South Wabash Avenue

As the 19th century tip-toed to a close the dominant Romanesque influence on the streets of major American cities began to wane. Peter J. Weber, a designer in Chicago’s leading architecture shop of D.H. Burnham and Company, helped introduce the Arts and Crafts Movement to the town’s streetscape with this boutique hotel in 1896. Typically these buildings would feature heights over five stories, rise to a flat roof, display uniform rhythmic window patterns, and abandon projections on the facade. Weber gave the upper floors of the Silversmith Moorish details in red brick and terra cotta and the lower floors a zigzag surround on the windows, typical of the turn-of-the-century European geometrical designs that inspired the Arts and Crafts movement. The new style suited the jewelry and silver trade in what is still called “Jeweler’s Row.”

TURN LEFT ON MADISON STREET. 

37.
Chicago Building
7 West Madison Street at State Street

The intersection of Madison and State streets is the 0-0 degree point of the city, from which all addresses north and south and east and west, begin. Over-stimulated civic boosters once called it the “World’s Busiest Corner.” In 1939, a government survey showed 265,376 pedestrians and 24,898 autos poured through it in a 12-hour period. Things have quieted greatly in the intervening years as retailers have shuttered and shoppers migrated to the suburbs and tonier districts in the city. This tower from 1904 was the creation of Holabird & Roche and is an early example of the Chicago school of architecture, sporting large “Chicago windows,” metal frame construction, distinctive bays, and terra cotta cladding. In 1997, the 16-story skyscraper was converted to a dormitory for the School of the Art Institute of Chicago.

38.
Carson, Pirie, Scott and Company Building (Sullivan Center)
33 South State Street at Madison Street

This was the last major commercial work by the influential architect Louis Henri Sullivan, an exemplary model of his decree that form follows function. An iron and steel framework supports the building that was designed in 1899 as a nine-story building but grew an additional three stories and down the block as well. In between the windows are lavish bands of light-colored terra cotta. The bronze-plated ornamental work above the rounded corner and the terra cotta were selected to be fire-resistant. Look up to see the cast iron ornamentation which adorns the first two floors; the horizontal effect, created by the alignment of the large “Chicago windows;” and the cylindrical main entry rotunda which rounds the corner of State and Madison Streets. The ironwork represents some of the most famous art of its kind in the world and best illustrates Sullivan’s ability to transform iron into lace. The building, now a National Historic Landmark and restored early this century, was built for dry goods merchant Schlesinger-Mayer who sold out to Carson Pirie Scott in 1904.

39.
Sears on State
2 North State Street

The most famous building associated with the one-time retail king was the Sear Tower but its flagship store was located on State Street at Van Buren from 1932 to 1986. After almost 20 years, Sears returned to State Street in this renovated 1905 building, designed by Holabird & Roche. It was built for another legendary retailer, the Boston Store. Charles Netcher opened hi store in 1873 and famously slept on showcase countertops as he built his emporium. Along the way he spied a hard-working buyer in the underwear department named Mollie Alpiner and married her in 1891. After Netcher died in 1905 Mollie took the reigns, constructed this building and parlayed the Boston Store form a $3 million moneymaker into a $20 million fortune as she ran the business for 42 years. The colonnade at the top of the building is a souvenir from the Netchers early days in retailing - as the building expanded it got pushed continually upwards.

TURN RIGHT ON STATE STREET. 

40.
The Reliance Building
32 North State Street

This groundbreaking skyscraper is the first in the world in which most of its surface area is composed mostly f plate glass windows. Legendary architect John Wellborn Root began construction of the building in 1890 but he died of pneumonia when only the base was finished. Charles B. Atwood, who designed several buildings for the 1893 World’s Columbian Exposition in Chicago, finished the building. The building did not age well and staggered to its recognition as a National Historic Landmark in 1970 by the National Park Service. The former retail space finally received a $27 million rehabilitation in 1999.

41.
Marshall Field and Company (Macy’s On State)
  
111 North State Street

Of all the merchant princes of the 19th century, none was richer than Marshall Field; when he died in 1906 he was said to have been the largest taxpayer in the United States. Field traveled west from the hills of Massachusetts in 1856 to become a clerk in the largest wholesale drygoods house in Chicago. Field’s salary was $400 a year. He slept on the premises and saved $200. He became a partner by 1860 at the age of 245 and made enough money supplying Union troops during the Civil War to buy into the business of Potter Palmer at 137 Lake Street, the town’s leading retailer. Palmer soon concluded that his present Lake Street location did not hold as much promise as a State Street address. State Street was little more than a muddy ribbon flowing through rows of dilapidated shacks but Potter quietly acquired all the property on State Street. He built a street 100 feet in width, erected a 6-story building and opened his doors. State Street was on its way to becoming one of the great shopping streets in the world. Field and his partner Levi Leiter leased the new building. This building, designed by Charles B. Atwood in a Renaissance Revival style, came along in 1892. Or at least the beginnings of this building. Over time Marshall Field’s swallowed the entire block and the retailing giant grew out and up. A street level facade attempts to unify the conglomeration but if you look up you can discern the antecedents of today’s building. For a time after 1907 it was the largest department store in the world. Marshall Field and Company was sold out of existence in 1982, beginning a chain of new ownership that culminated in Federated Department Stores taking over in 2005. Federated did the unthinkable, jettisoning the Marshall Field nameplate in favor of its New York Macy’s brands. Some outraged Chicago shoppers still haven’t been back and vowed never to meet under the iconic clock on State Street again.  

TURN LEFT ON WASHINGTON STREET.

42.
First Methodist Episcopal Church
77 West Washington Street

This is the oldest church in Chicago, founded by Methodist circuit riders in 1831, six years before the City of Chicago was incorporated. The first church was a log cabin sited north of the Chicago River in 1834. Four years later it was hauled to the river, floated across and rolled on logs to its present site at the corner of Washington and Clark streets. Four buildings later the congregation is still there. The present 568-foot skyscraper, faced in Indiana limestone, was dedicated in 1928. In 1952 a sky chapel donated by the Walgreen’s Drug family came online.

43.
The Burnham Center
111 West Washington at Clark Street

This was the last skyscraper to come out of Daniel Burnham’s influential shop, in 1913, constructed for Marshall Field and named for the developer’s hometown of Conway, Massachusetts. Today the building carries the architect’s name rather than the financier’s. The massive 21-story office building rests on concrete caissons which are sunk 100 feet to bedrock. The outside facing being granite terra cotta and enameled brick. Sixteen electric passenger elevators provided the fastest and most efficient service of the day to the upper floors. Lead designer Peirce Anderson is credited with many of the Beaux Arts decoration of the 300-foot skyscraper marked by rounded corners.

TURN RIGHT ON CLARK STREET.

44.
Richard J. Daley Center
55 West Randolph Street between Clark and Dearborn streets

This was the Chicago Civic Center when the International Style tower was completed as the town’s tallest building. A week after his death in 1976 the building was renamed for 21-year mayor and “the last of the big city bosses,” Richard J. Daley. Only his son Richard M. Daley, who began in office in 1989, served longer as mayor of Chicago. The 648-foot building features Cor-Ten, a self-weathering steel that is designed to rust, actually strengthening the structure and giving the building its distinctive red and brown color. Daley Center features only 30 floors inside, half the number typically contained in a building of this height; it is the tallest structure in the world with fewer than 40 stories. The untitled sculpture in the plaza to the south of Daley Center is a gift to the city from Pablo Picasso, even though the artist never visited Chicago. Picasso actually donated a 42-inch model from which U.S. Steel fabricated the 50-foot, 162-ton statue using the same corrosive tensile steel as the Daley Center.

45.
Chicago Title Tower
161 North Clark Street at Randolph Street

Tens of thousands of people took their first steps in Chicago here when this was the site of the Greyhound Bus Terminal. In 1990, this 50-story granite-and-glass tower skyscraper on the site; its defining feature is an east-facing slant at its top. It was supposed to be part of tower tandem but its northern partner was never built.

TURN RIGHT ONRANDOLPH STREET. TURN LEFT ON DEARBORN STREET.

46.
Goodman Theater
170 North Dearborn Street

William Owen Goodman migrated to Chicago from Pennsylvania in 1868 at the age of 20 and found work as a bookkeeper for the Menominee River Lumber Company. As he worked began investing in his own timberlands and built one of the great lumber fortunes of the Midwest. In 1914 Shaw created this Neoclassical-Georgian Revival brick mansion for the Goodman family. Four years later the Great Flu Pandemic of 1918 claimed Goodman’s son Kenneth Sawyer, a playwright, and he donated $250,000 to the Art Institute of Chicago to establish a professional repertory company and a school of drama in his memory. Chicago-born Howard Van Doren Shaw designed the original Goodman Theatre that opened in 1925. The new building next door opened in 2000, named the Albert and the Owen, after two members of the Goodman family who continue to be major donors.

47.
Delaware Building
36 West Randolph Street at Dearborn Street

The Delaware Building stands as a rare relic ofthe massive rebuilding effort that swept the city after the 1871 Great Chicago Fire. Still retaining its Italianate facade, it is significant for its early use of a precast concrete façade. Teh building was constructed with five floors above a basement; two additional stories came along in 1889.

48.
Oliver Building
159 North Dearborn Street

Thomas Oliver was a Canadian who migrated to Iowa to serve as a Methodist minister. Seeking a way to produce more legible sermons, Oliver began tinkering with a version of a typewriter fashioned from strips of tin cans. In 1891 he received a patent for his typewriter. Four years later Oliver rounded up enough investors to walk away from his ministry at the age of 42 and begin making the world’s first typewriters where the text was visible to the typist as it was entered. In 1908 the Oliver Typewriting Company moved into this building designed by Holabird & Roche that typified the principles of the Chicago Schoolof architecture then coming into vogue. Look up into the cast iron exterior features typewriter-related motifs an the Oliver name. Thomas Oliver died unexpectedly in 1909 and the company went bankrupt in 1928. The license to manufacture the machines was purchased and Oliver typewriters continued to be manufactured until 1959.

TURN RIGHT ON LAKE STREET. TURN RIGHT ON STATE STREET.

49.
Chicago State Street Studio
190 North State Street

This building began life as the State-Lake Theater back in 1919, a treasure in the RKO chain of movie houses designed by the Rapp brothers. In the mid-1980s, the building was converted into a television studio for WLS, the Chicago outlet of the American Broadcasting Company. WLS-TV and WLS-Radio were owned by Sears Roebuck and Company and the call letters stand for “World’s Largest Store.” 

50.
Page Brothers Building
177-91 North State Street in the Loop

Cast iron became a popular building material in the middle of the 19th century, a quick and affordable way to erect commercial buildings. The iron was easily fashioned into decorative facades, often in an Italianate style. The building was constructed for the Page Brothers by John M. Van Osdel in 1872. Osdel, then 61 years old, was considered Chicago’s first prominent architect. Osdel placed the cast-iron faced, the last remaining in the Loop, on the Lake Street elevation, which was the town’s prime retail street at the time. The building’s west facade (State Street) was remodeled and another floor added in 1902, reflecting the reorientation of commercial activity from Lake to State Street.

51.
Chicago Theater
175 North State Street

This was the flagship theater in the Balaban and Katz chain of over 100 movie houses. More than four million dollars was poured into its construction in 1921 with the brother tandem of Cornelius and George Rapp creating a French Baroque palace that could seat nearly 4,000 patrons. Accompanying the silent films was a 50-piece orchestra and 29-rank Wurlitzer organ. During its 40 years of operation the marquee became an instantly recognized emblem of the city in photographs and movies. The Y-shaped figure behind the horizontal word Chicago on the State Street marquee is the city’s municipal badge, symbolizing the forked Chicago River at Wolf Point. The current marquee, part of a multi-million revitalization of the theater, is a reproduction - the original was donated to the Smithsonian Institution. 

52.
Gene Siskel Film Center
164 North State Street

The Film Center of the School of the Art Institute of Chicago began in 1972 as a way to premier new American and foreign films, revive classics, present retrospectives, and stage festivals of international scope. With over 100 programs each month it is one of the world’s largest venues of its kind. In 2001 it was named for film critic and Advisory Board member Gene Siskel.

53.
Joffrey Tower
8 East Randolph Street at State Street

Robert Joffrey, then 23 years old, formed his modern ballet company in 1954and toured the country with a six-dancer ensemble in a station wagon and U-Haul trailer. The Joffrey Ballet relocated to Chicago in 1995, several years after the founder’s death in 1988. This is their first permanent home, raised in 2007 on the site of the flagship Walgreen’s Drug store.

AT RANDOLPH STREET TURN RIGHT AND WALK A FEW STEPS DOWN TO SEE...

54.
The Oriental Theater
24 West Randolph Street

The consortium of A. J. Balaban, Barney Balaban, Sam Katz, and Morris Katz organize din 1916 and operated over 100 theaters in the Midwest, including some 50 in the Chicago area and a half-dozen in the Loop itself. Balaban and Katz often used the celebrated Rapp brothers to design their theaters and the duo provided an exotic Indian motif for the Oriental in 1926. The site was historic and infamous - in 1906 a fire swept through the Iroquois Theater here, claiming 602 lives. The exterior remained intact and it was used to rebuild as the Colonial but the building was finally razed to make way for the Oriental. The theater followed a familiar arc as it declined from its heyday as a movie palace into exploitation films in the 1970s and then vacancy. But it was one of the lucky ones - it escaped the wrecking ball and has been restored. It was reported that it required 4,000 gallons of paint, 12,500 square feet of gold leaf, and an astounding 62,500 square feet of aluminum leaf to complete the project.

TURN AND RETRACE YOUR STEPS ON RANDOLPH STREET TOWARDS STATE STREET. CONTINUE ACROSS, PAST MARSHALL FIELD’S (MACY’S), UNTIL YOU REACH MICHIGAN AVENUE. CROSS TO RE-ENTER GRANT PARK AND THE START OF THE TOUR.