Loop District Architecture Walking Tour, Chicago

Loop District Architecture Walking Tour (Self Guided), Chicago

Chicago features an outstanding architectural legacy, having long been connected with some of architecture's most important names: Frank Lloyd Wright, Louis Sullivan, Mies van der Rohe, Holabird & Root, and others. The multi-layered Loop District, in particular, offers an extensive number of Chicago’s famous architectural “must-sees” – from modern skyscrapers to historic buildings that were instrumental in their development.

Start your walking tour with Aqua Tower’s rippling facade of irregular balconies, praised by architecture critics for its fascinating visual impact. One of the tallest high rises built during Chicago’s skyscraper boom of 2000-2009, it is noted for the unique design of its balconies, which give the building a remarkable silhouette.

Meanwhile, the Willis Tower (formerly known as the Sears Tower) is still the 2nd-tallest building in the Western Hemisphere, standing in the western Loop – the heart of the city's financial district. Its neighbouring landmark, the historic Rookery Building (1888), best exemplifies the development of the Chicago school with a unique style featuring exterior load-bearing walls and an interior steel frame, which at the time provided a transition between accepted and new building techniques.

Among other historic architectural gems are the Chicago Theatre – one of the city’s most-photographed structures for its flashing marquee built in 1921; the iconic Union Station, whose high ceilings and Corinthian columns inspire a sense of awe since 1925; or the Harold Washington Library Center, whose dramatically beautiful exterior, featuring five massive owls looking down from the top, is hard to miss.

Take this self-guided walking tour to explore the Loop District’s most iconic constructions that have contributed to a great deal of Chicago’s worldwide fame.
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Loop District Architecture Walking Tour Map

Guide Name: Loop District Architecture Walking Tour
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 22
Tour Duration: 3 Hour(s)
Travel Distance: 4.7 Km or 2.9 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Tribune Tower
  • Wrigley Building
  • London Guarantee Building
  • One Illinois Center
  • Aqua (skyscraper)
  • Carbide & Carbon Building
  • Marina City
  • Chicago Theatre
  • Richard J. Daley Center
  • James R. Thompson Center
  • Chicago City Hall & County Building
  • 190 South LaSalle
  • Rookery Building
  • Chicago Board of Trade Building
  • Marquette Building
  • Kluczynski Federal Building
  • Monadnock Building
  • Fisher Building
  • Manhattan Building
  • Harold Washington Library Center
  • Fine Arts Building
  • Auditorium Building
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Tribune Tower

1) Tribune Tower

Just a few steps from the Wrigley Building, the Tribune Tower rises like a Gothic cathedral with its flying buttresses and intricate scrollwork. Erected in 1925, this building was conceived as the headquarters for the 'Chicago Tribune', a project backed by the deep pockets of the newspaper's eccentric editor-publisher, Robert "The Colonel" McCormick. The dapper McCormick and his scruffy co-publisher, Joseph Patterson, initiated a contest in 1922 to celebrate the Chicago Tribune's 75th anniversary. They offered a total of $100,000 in prizes to architects worldwide, who would submit designs for the "most beautiful office building in the world".

The winning design came from the American duo, John Mead Howells and Raymond Hood, who drew inspiration from Britain's Arts and Crafts movement, which rebelled against angular, mass-produced decoration. As a result, the tower's ornate details feature a plethora of flora, fauna, and figures from ancient Greek storyteller Aesop's fables intricately woven into the stonework above the main entrance.

Be sure to explore the main lobby, where you'll discover remarkable decorative elements including quotations promoting a free press, etched across nearly every inch of marble. There's a colossal relief map of North America on the main wall, made from a peculiar mix of plaster and old dollar bills; apparently, the original design included a substantial portion of South America, but the intensely patriotic Colonel decided to emphasize the United States by truncating two feet from the bottom.

Ever since the 'Chicago Tribune' newspaper relocated from the building in 2018, the neo-Gothic skyscraper has been transformed into condominiums. This, however, hasn't affected the building's façade. Visitors can still marvel at the fragments from renowned global landmarks embedded therein, including the Parthenon, the Taj Mahal, Westminster Abbey, the Alamo, Saint Peter's Basilica in Rome, the Great Wall of China, and Bunker Hill.
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Wrigley Building

2) Wrigley Building

Perched along the river, at the bend of Michigan Avenue, is the Wrigley Building, a towering symbol of old Chicago deeply ingrained in the hearts of locals. Renowned for its radiant white exterior, this "Jewel of the Mile" stands majestically, with its grandeur enhanced by the mirrored image in the water when looked at from either the east or west sides.

Yet, the Wrigley Building is more than just a beloved symbol; it encapsulates the essence of Chicago's architectural history up to the 1920s. Designed by the talented young architect Charles Gerhard Beersman, the structure's tripartite division draws inspiration from European traditions, a common practice among Chicago's commercial architects since the city's rebirth following the 1871 fire. Beersman was inspired by the dazzling effects of the 1893 White City designs in Chicago, leading him to embellish the building with sparkling terra-cotta cladding.

He selected six shades of tiles, ranging from creamy white, at the base, to blue-white, at the summit, creating an ascending brilliance. When the night falls, an array of floodlights on adjacent structures bathes the Wrigley Building in a captivating, ever-intensifying luminance. Whether it's noon or midnight, the edifice stands as a brilliant beacon against the sky.

Just next door, at 401 North Wabash Avenue, the mirrored oval Trump International Hotel & Tower reached its peak in September 2008; soaring to 92 stories, it was briefly the second-tallest building in the United States, after the Sears Tower. Initially, Donald Trump had ambitious plans to make it the world's tallest building, but these were scaled back in the aftermath of the September 11 attacks. Impressively attuned to its surroundings, the tower echoes the curve of the river and pays homage to the Wrigley Building. Inside, it houses a luxurious hotel, opulent condos, and a fine dining establishment.

Tip:
Don't miss the chance to step inside the Wrigley Building's lobby during regular business hours to admire its extensive brasswork.
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London Guarantee Building

3) London Guarantee Building

The London Guarantee & Accident Building, a stalwart of Chicago's skyline since the 1920s, embodies the city’s architectural flourish during a period of rapid growth. Completed in 1923, this Beaux-Arts masterpiece was designed by Alfred S. Alschuler for the London Guarantee & Accident Company, a British insurance firm. The building's design reflects the opulence and ambition of its time, mirroring the grandiosity seen in Chicago’s early skyscrapers and paying homage to the city's architectural legacy established by the World's Columbian Exposition of 1893.

The London Guarantee Building stands as a prominent example of the Beaux-Arts style, characterized by its classical elegance and intricate detailing. Its stone façade showcases Corinthian columns and Roman figures, which are hallmarks of the style. These classical elements imbue the structure with a sense of timeless grandeur and sophistication, placing it firmly within the architectural context of early 20th-century Chicago.

A striking feature of the building is its cupola, which crowns the 22-story tower with dramatic flair. The cupola’s ringed colonnade and domed top extend the building’s height and add a sense of vertical grandeur, serving as a visual counterpoint to the nearby Wrigley Building. This architectural choice not only enhances the building’s prominence on the skyline but also underscores its significance as part of Chicago’s historic urban fabric.
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One Illinois Center

4) One Illinois Center

One Illinois Center, also known as 111 East Wacker, stands as a significant testament to Mies van der Rohe's architectural legacy. Completed in 1967, this skyscraper was the first building erected on the site of a former rail yard that had once housed Fort Dearborn. Mies van der Rohe’s design embodies the principles of International Style architecture, reflecting his refined approach and the ideas he carried from Germany before World War II.

The building’s design is a classic example of Mies’s commitment to the principles of International Style. It emphasizes volume through the use of thin planes of glass that enclose space, moving away from the traditional solid mass of brick or stone. The façade, rather than featuring a central opening or traditional symmetry, showcases a regular rhythm of columns that create a distinct and regular appearance. The aesthetic appeal of 111 East Wacker lies not in applied ornamentation but in the elegance of its materials and the technical perfection with which they are assembled.

The building’s sleek and minimalist form celebrates industrial materials in a way that aligns with its historical context. Situated on a site once dedicated to industry, the structure’s use of glass and steel highlights Mies’s ability to elevate basic construction into a form of high art. The careful detailing and proportional elegance of the design make One Illinois Center a notable example of Mid-Century Modern architecture, marking a significant moment in the evolution of skyscraper design.
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Aqua (skyscraper)

5) Aqua (skyscraper)

It took nearly five decades, but with the completion of Aqua, designed by Jeanne Gang, the iconic towers of Bertrand Goldberg's Marina City finally have a true contender in terms of architectural boldness that captures the essence of Chicago on a global scale. Soaring to a height of 859 feet, Aqua also holds the distinction of being the tallest building designed by a female lead architect, garnering numerous awards shortly after its construction.

Like Marina City, Aqua is a mixed-use complex, blending condominiums, apartments, commercial spaces, and a hotel. However, in contrast to Marina City's unconventional circular design, Aqua takes on the shape of a more typical rectangular tower. What sets it apart is Gang's ingenious incorporation of the concept of "vertical topography" to create a multifaceted texture on the building's façade, breaking away from the conventional linearity that lies beneath.

The edges of the floor slabs continuously vary from one floor to another. Balconies extend out as far as twelve feet in areas with optimal views or the need for sun shading. In contrast, some balconies are as narrow as two feet or even omitted, with the curtain wall behind them employing high-performance, reflective glass to form "pools" — resembling watery voids nestled within the vertical contours of the undulating balconies. Meanwhile, atop the building, an expansive 80,000-square-foot terrace houses lush gardens designed by landscape architect Ted Wolff, complemented by a swimming pool and other amenities.

When viewed head-on from a distance, especially on overcast days, Aqua's distinctive features can blend into the city skyline. Yet, when illuminated by light and observed up close, the building's visual allure becomes almost mesmerizing. Its ever-changing façade makes it elusive to the eye, and standing beneath one of its corners and looking up, the absence of traditional grid points to anchor your vision creates a sense of perpetual motion across Aqua's surfaces.

Why You Should Visit:
One of the most unique buildings in the world; each balcony is unique in size and shape giving the appearance of water flowing in waves.
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Carbide & Carbon Building

6) Carbide & Carbon Building

The Carbide & Carbon Building stands as a dazzling testament to the opulence and grandeur of the 1920s. Commissioned by the Carbide and Carbon Company, which was renowned for developing the first dry cell battery, this striking skyscraper was designed by the Burnham Brothers and completed in 1929. The building’s exterior exudes a sense of luxury with its polished black granite, green and gold terra cotta, and gleaming gold leaf accents. Its Art Deco design is characterized by dramatic and lavish detailing, setting it apart on Chicago's skyline.

The lobby of the Carbide & Carbon Building is a quintessential example of the period's extravagance, featuring frosted glass fixtures and Belgian marble. Originally intended to showcase the company’s products, the lobby remains an impressive introduction to the building’s opulent character. At the top, the building’s cap is adorned with genuine 24-karat gold, though it is incredibly thin—only one five-thousandths of an inch thick—adding a touch of understated luxury.

Despite its early promise, the building's expansion plans were halted by the market crash of 1929, and a planned sister structure was never realized. In 1994, the Carbide & Carbon Building was landmarked, and in 2004, it underwent a significant $106 million restoration. Following its sale to a realty company, it was transformed into the Hard Rock Hotel, continuing to stand out as one of the most unique and historic structures in Chicago's architectural landscape.
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Marina City

7) Marina City

Architect Bertrand Goldberg, clearly a fan of curves over corners, brought his artistic flair to life in these quirky residential towers. Some folks say they resemble corncobs, but Goldberg, with his artistic flair, fancied them as sunflowers—each apartment's curved balcony resembling a petal. This design gave the rigid International Style a run for its money, challenging the high-rise norm that dominated architectural trends in the 1950s.

In an era when many urban workers were flocking to the suburbs, Goldberg and his client, the Building Service Employees International Union, had a hunch. They believed that city-dwellers, especially singles and the childless, still wanted proximity to their workplaces in the Loop. Their gamble paid off handsomely, and this complex became a trailblazer for similar projects sprouting up around the Loop. Plus, it spent plenty of time in the Windy City limelight as one of the most snapped buildings.

To make urban living in a previously railroad-centric area appealing, Goldberg thought outside the box. He threw in shops, a restaurant, a health center, a pool, a skating rink, an exhibition space, a theater, a marina, a bowling alley, and even an office tower. It was marketed as a "city within a city", offering "24-hour urban living", slyly contrasting suburban life, where commuters only used their homes for snoozing.

Built between 1964 and 1968, these towers still house condominiums with spectacular views (although their unique shape poses some interior decorating puzzles). Oh, and don't forget about the first 19 stories of each tower—the open spiral parking garages. The complex also houses six restaurants, as well as the House of Blues, Hotel Chicago, a sprawling bowling alley, and even its own marina. It's like a sunflower in the middle of the urban jungle!
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Chicago Theatre

8) Chicago Theatre (must see)

The unmistakable vertical "CHICAGO" sign and marquee of the Chicago Theatre are impossible to overlook, as is its façade, which draws inspiration from the iconic Triumphal Arch in Paris. This building ranks among the city's most frequently photographed structures and earned the moniker "the Wonder Theatre of the World" upon its grand opening in 1921. Constructed immediately after the devastating Great Fire, it mimics the style and materials of the destroyed buildings, having one of the Loop's last surviving cast-iron facades (a feature that fell out of favor due to its susceptibility to heat, which could cause it to collapse along with the masonry walls it supports).

However, the Chicago Theatre is renowned primarily for its sumptuous interior, adorned with exquisite murals, crystal chandeliers, and bronze light fixtures. The entire lobby is a homage to the Royal Chapel at Versailles, featuring a grand staircase modeled after the Paris Opera House, gracefully ascending to the mezzanine and balcony levels. The auditorium, with a seating capacity of 3,800, offers exceptional sightlines, owing to the uniquely shaped site.

During its early years, the theater screened silent films accompanied by live orchestras and the in-house Wurlitzer theatre organ. Today, it hosts a wide array of performances, including post-Broadway plays, musicals, concerts, and comedy shows. Visitors can partake in informative tours that provide insights into the baroque interior, allow them to stand on the same stage graced by legendary entertainers like John Philip Sousa, Duke Ellington, Ellen DeGeneres, and Beyoncé, and even offer backstage access, where autographed walls bear testament to the venue's rich history.
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Richard J. Daley Center

9) Richard J. Daley Center

The Richard J. Daley Center, completed in 1965, stands as a striking example of Mid-Century Modern architecture and the International Style’s “skin and bones” aesthetic. One of the building’s most notable features is its distinctive exterior, clad in Cor-Ten steel. This unpainted steel develops a natural rust over time, creating a unique, permanent protective coating that requires minimal maintenance. Complementing the rust-colored steel panels are bronze-tinted glass windows, which together create a harmonious and eye-catching facade.

The true marvel of the Daley Center, however, lies in its structural innovation. The building is supported by just 16 steel columns—12 on the perimeter and four surrounding the central elevator core. This minimalist column arrangement allows for expansive, column-free interior spaces. Each floor is supported by Warren trusses, which are notably thick to span the considerable distances between the columns. The façade of the building visually emphasizes its structural components, making the engineering prowess an integral part of its design.

Despite its relatively modest 31 floors, the Daley Center reaches an impressive height of 648 feet, comparable to that of many 50- to 60-story skyscrapers. This vertical impact is achieved through high ceilings on each floor, with some courtrooms extending to 26 feet in height. Architect Jacques Brownson of C.F. Murphy Associates meticulously designed the columns to taper as they ascend, reflecting the decreasing loads as the building rises. This thoughtful design detail not only enhances the building’s aesthetics but also underscores the engineering sophistication behind its construction.
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James R. Thompson Center

10) James R. Thompson Center

The James R. Thompson Center, designed by Helmut Jahn, is a striking example of Postmodern architecture in Chicago, distinguished by its vibrant colors and distinctive shape. Completed in 1985, the building was conceived as a symbol of transparency and accessibility, reflecting the state of Illinois’ commitment to public service. Its design merges functionality with visual impact, intended to represent an open and welcoming government space. The Thompson Center consolidates 50 state agency offices into a single, easily accessible location, making it both a functional government center and a community hub for shopping and dining.

Architecturally, the Thompson Center makes a bold statement with its non-traditional design. The building's southeast profile features a curved blue glass facade and salmon-colored steel, evoking the grand domes of historic government buildings while breaking away from the strict linearity of modernism. This dome-like shape pays homage to the Illinois State Capitol in Springfield, adding a historical reference to its otherwise contemporary appearance. The gridded walls that face LaSalle and Lake Streets provide a more traditional façade, creating a juxtaposition with the building’s more expressive elements.

Inside, the Thompson Center continues to impress with its expansive, skylit rotunda. Spanning 160 feet in diameter and rising 13 stories, this central space is lined with open office balconies and features a large circular cutout that overlooks a busy food court and various state offices. The open design, with its continuous flow of escalators and exposed elevators, adds to the building's dynamic and bustling atmosphere. The rotunda serves as a vibrant heart of the complex, enhancing its role as a “peoples’ center.”

Maintaining a comfortable climate within this large glass structure presents a unique challenge. To address this, the building utilizes an innovative thermal storage system. Ice slush is created overnight when electricity costs are lower and stored in basement tanks. This chilled slush is then used to cool the building during the day and re-frozen overnight, balancing efficiency and comfort in a building known for its striking aesthetic and significant public function.
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Chicago City Hall & County Building

11) Chicago City Hall & County Building

This structure essentially functions as an office building—or more precisely, two office buildings designed around light wells, one of which has its office spaces interrupted for two stories to accommodate the City Council. The primary objective was to construct an eleven-story structure that wouldn't give the impression of a typical skyscraper. This feat was achieved by doubling the size of the exterior façade, reducing the number of windows, and introducing Chicago's largest columns at the time—imposing seventy-five-foot-high, hollow columns composed of fifteen curved granite segments. The Corinthian capitals alone equal the height of an entire floor! The support for these purely ornamental elements necessitated the use of ten-foot-diameter caissons.

Designed in the Classical Revival style, the building received its official dedication in 1911. The entrance to the Chicago City Hall showcases four relief panels sculpted in granite, each representing one of the four main concerns of city government: playgrounds, schools, parks, and water supply. Upon entering the premises, visitors are welcomed by intricate marble stairways and bronze tablets that pay tribute to the historical city halls of Chicago, spanning from 1837 to the present day.

In 2006, a green roof was installed on the City Hall section of the building, serving as an experiment to study the impact of green roofs on urban heat islands, rainwater runoff, and the suitability of various green roofs and plant species for Chicago's climate. It also facilitated energy consumption comparisons with the conventionally roofed County Building.
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190 South LaSalle

12) 190 South LaSalle

When strolling along LaSalle Street in Chicago’s financial district, 190 South LaSalle might initially blend into its surroundings, thanks to its understated masonry facade. The building’s design deliberately harmonizes with the surrounding structures, creating a grand but somewhat subdued street-level presence. However, this façade contrasts sharply with its dramatic impact on the city skyline. The building’s distinctive green gabled roof stands out, marking it as a notable landmark amidst Chicago’s diverse architectural landscape.

Designed by architects Philip Johnson and John Burgee, 190 South LaSalle exemplifies Postmodern architecture with its playful scale and vibrant symbolism. This style, emerging in the 1980s and '90s, represents a departure from the restrained International Style championed by Mies van der Rohe. Postmodernism often embraces exaggerated decorative elements and bold colors, which is evident in the oversized features and striking roof of 190 South LaSalle. The building reflects this architectural freedom, combining traditional Chicago architectural language with innovative, eye-catching elements.

In its blend of classic and contemporary influences, 190 South LaSalle manages to be both a subtle presence at street level and a striking visual landmark from afar. Its design cleverly navigates the balance between integration and distinction, offering a fascinating study in Postmodern architecture’s embrace of dramatic flair and historical reference.
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Rookery Building

13) Rookery Building

The Rookery Building is a cornerstone of Chicago's rich architectural heritage, showcasing the work of the city's two great design architects, John Wellborn Root and Frank Lloyd Wright. The building was designated a Chicago Landmark in 1972 and was added to the list of National Historic Landmarks in 1975.

After the Great Chicago Fire of 1871, a temporary city hall was built at the corner of LaSalle and Adams Streets around a water storage tank. The tank was a hangout for crows, and the locals called it "the Rookery." This was a reference to the birds and also a reference to corrupt politicians in the building.

In 1888, architects Daniel Burnham and John Wellborn Root completed their 11-story commercial building at the Rookery site and named it "Rookery." John Wellborn Root carved a pair of rooks into the Romanesque main entrance on La Salle Street.

The Rookery was truly transitional, with elevators, fireproofing, and electric lighting. John W. Root planned to have as much natural light in the building as possible. He developed a hollow square plan. Offices in the building would be lighted from the outside or the central two-story light court with its glass-paneled ceiling and grand staircases.

In 1905, Burnham commissioned Frank Lloyd Wright to renovate the interiors, especially the "light court." Wright removed Root's ironwork and replaced it with Carrara marble incised with gilded arabesque designs. The Rookery became a white and gold commercial center.

The double set of ornate stairs winds upward. A wrap-around balcony climbing up to the second floor creates the sense of "clockwork." The facade of the Rookery is of marble, terra cotta, and brick. The overall style is Romanesque, featuring touches of Roman Revival and Queen Anne. A second renovation in 1931 included Art Deco details.

The Frank Lloyd Wright Trust conducts tours Mondays through Fridays. Inside Chicago has daily walking tours of the Rookery. The Rookery has been a locale for films such as Home Alone 2 and The Untouchables.
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Chicago Board of Trade Building

14) Chicago Board of Trade Building

The Chicago Board of Trade Building stands as a commanding symbol of Chicago's financial district. This 45-story skyscraper, a paragon of Art Deco design, was conceived during the height of the Art Deco era by architects John A. Holabird and John Wellborn Root Jr., both prominent figures in architectural history. Completed in 1930, the building reflects the bold and dynamic spirit of its time, asserting its importance in both the cityscape and the economy.

The Chicago Board of Trade Building's design showcases key Art Deco features, including a striking vertical emphasis achieved through its use of gray Indiana limestone piers and dark, recessed windows. The building's streamlined, geometric ornamentation and abstract details exemplify the era's aesthetic, while its throne-like massing reinforces its grandeur and authority. These elements work together to create a facade that is both monumental and elegant, encapsulating the sophistication of Art Deco.

Topping the building is a distinctive pyramidal roof adorned with a faceless aluminum statue of Ceres, the Roman goddess of agriculture, crafted by artist John Storrs. The statue’s machine-like appearance and the clean lines of her garment further embody the Art Deco emphasis on stylization and modernity.
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Marquette Building

15) Marquette Building

Much like a well-fitted slipcover on a sofa, the Marquette, erected in 1895, conceals its structural steel frame beneath a clean, geometric facade. While its base showcases roughly cut stone and an ornate cornice crowns its summit, the majority of the building reflects the framework upon which it was constructed. All the offices, aligning with the building's arms, have a window either facing the street or the light well. This design, combined with the structural and aesthetic wall treatment, ensures abundant natural light within the interior.

Named in tribute to Jacques Marquette, a Jesuit priest and explorer, the building draws inspiration from his 1674–75 journal, which provided the first European description of Chicago's site. Owen F. Aldis, a real estate developer, amateur historian, and original owner, translated Marquette's journal in 1891, serving as the catalyst for the building's name and decorative theme. While exterior relief sculptures depict events related to Marquette's expedition, the intimate two-story lobby resembles a true jewel box. Shimmering bronze fixtures contrast with a Tiffany glass mosaic portraying the adventures of the French missionary while, nearby, bronze reliefs above the elevator doors depict French explorers and Native Americans. If you continue through the lobby, you'll find an exhibition on the structure's history and recent restoration, sponsored by the MacArthur Foundation, a prominent tenant.

Architects Holabird and Roche, who first met as draftsmen in the office of pioneering skyscraper designer William L. B. Jenney, established their firm in the early 1880s. Renowned for their work in the Chicago commercial style, they left an indelible mark on this edifice.
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Kluczynski Federal Building

16) Kluczynski Federal Building

The Kluczynski Federal Building, part of the Chicago Federal Center designed by Ludwig Mies van der Rohe, is a prime example of the architect’s philosophy of "Less is more." Completed in 1974, this steel and glass complex epitomizes Mies' commitment to simplicity, modernity, and efficiency. The design marked a significant shift in public architecture, aligning with Mies' vision of creating functional, streamlined structures. The building’s construction was part of a broader urban renewal initiative led by Mayor Richard J. Daley, aimed at revitalizing downtown Chicago and reinvigorating its struggling economy.

The Chicago Federal Center’s three-building complex stands as a testament to Mies' rigorous design principles. Constructed on a precise grid system, every component—from columns and light fixtures to benches and pavers—aligns perfectly, embodying the architect’s belief that "God is in the details." This meticulous attention to alignment and proportion is evident throughout the complex, offering an engaging visual experience for those who appreciate architectural precision. Visitors are invited to explore the plaza, where the alignment of architectural elements creates a harmonious and meticulously ordered environment.

Beyond its architectural significance, the plaza of the Federal Center has become a lively urban space, hosting festivals, farmers markets, and public demonstrations. This active use of the space underscores the dynamic interaction between citizens, businesses, and government, fulfilling the revitalization goals set forth in the 1959 urban renewal plan. Despite its rigid design, the Federal Center is recognized for its "monumental urban presence," a phrase coined by architecture critic Franz Schulze, capturing the building’s impressive impact on the cityscape.
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Monadnock Building

17) Monadnock Building

The Monadnock Building in Chicago stands as a fascinating testament to the evolution of architectural design and engineering in the late 19th century. Built in two distinct phases, the Monadnock is a structural and stylistic juxtaposition that highlights the rapid advancements and shifts occurring in the field of architecture at the time.

The northern half of the Monadnock Building, completed in 1891 and designed by the renowned architectural firm Burnham & Root, features a daring, stripped-down facade. This section of the building embraces the load-bearing brick wall tradition, with its exterior walls layered brick upon brick. The building’s undulating bay windows, supported by cantilevered steel, showcase an early use of structural steel technology.

Despite the thick, six-foot brick walls at the corners, which provide substantial support, the central areas of the building are reinforced by a hidden steel framework. The design’s stark minimalism, contrasted with the battered base and projecting bays reminiscent of ancient Egyptian columns, foreshadows the future embrace of simplified, unadorned facades that would characterize modern architecture.

The southern half of the Monadnock, designed by Holabird & Roche and completed just two years later, marks a notable departure in style and technique. This section of the building was constructed using a more advanced approach, with a brick and terra cotta facade that does not bear the building’s weight. Instead, it is suspended from a rigid metal frame, allowing the weight to be transferred to the ground through the frame. This innovative method demonstrates a significant shift towards the use of steel in construction and reflects the ongoing experimentation and technological progress of the era.
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Fisher Building

18) Fisher Building

A Neo-Gothic landmark with a steel frame, the Fisher Building stands at a towering 275 feet in Chicago's Loop community area. When it was originally completed in 1896, it was one of only two 18-story buildings in the city, the other being the Masonic Building. Remarkably, it remains the city's oldest 18-story structure to this day, having never been demolished. In a complete reversal of fate, the building underwent a restoration process in 1998, when it was sold and slated for conversion from an office building into rental apartments.

The extensive restoration effort focused on its ornate facade, adorned with marine-themed motifs (as well as several eagles, dragons and other mythical creatures) as a nod to its developer, Lucius G. Fisher. This intricate process involved replacing over 6,000 terra-cotta elements. Furthermore, the previously destroyed main entrances on Dearborn Street and Plymouth Court were faithfully re-created, and 1,200 wood-frame windows, exemplary of the Chicago School style, were either repaired or replaced. The interior features restored mosaic flooring and Carrara marble walls, while the main lobby blends elements of both restoration and new design.
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Manhattan Building

19) Manhattan Building

Following the devastating Great Fire of 1871 that laid waste to downtown Chicago, ambitious architects swarmed the city, capitalizing on a unique opportunity: a multitude of eager clients demanding fresh designs, and a near absence of architectural constraints hindering daring experimentation. Even as the debris was being cleared, William Le Baron Jenney was at the forefront of shaping what would become the Chicago School of architecture.

As the senior figure among this group, Jenney made a seminal contribution to the style and the future of skyscrapers. He achieved this by pioneering the use of an internal steel frame, rather than thick external walls, as the primary support structure for a building's weight. Regrettably, his 1885 Home Insurance Building, often considered the world's first skyscraper, no longer stands. However, his 1891 Manhattan Building remains a compelling testament to his sturdy and practical architectural achievements.

Dubbed "Hercules" by awestruck visitors to the 1893 World's Columbian Exposition, the Manhattan Building was a trailblazer in numerous aspects. It was the inaugural tall building to employ skeleton construction throughout, the first sixteen-story structure in the United States, briefly the tallest building worldwide, and the pioneer in incorporating a structurally advanced wind-bracing system. Its distinctive bay windows allowed natural light to penetrate interior spaces, and the combination of a granite facade for the lower floors and brick facade for the upper stories helped alleviate the strain on the internal steel framework. Moreover, the north and south bays were cantilevered to prevent overburdening the foundations of neighboring buildings.
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Harold Washington Library Center

20) Harold Washington Library Center

Opened in 1991 and named in honor of Chicago's first African American mayor, this building emerged as the winning design following a highly publicized 1988 competition. It notably presented the most overtly traditional approach among the diverse proposals conceived to house the main library collection, which had languished in temporary quarters for a decade. Architected primarily by Thomas Beeby, the structure pays homage to Neoclassical institutions while avoiding slavish adherence to all their architectural particulars.

This granite-and-brick edifice, colossal and somewhat whimsical, almost assumes the role of a uniquely postmodern tribute to Chicago's rich architectural heritage. The robust and textured ground level pays homage to the Rookery, while the stepped-back, arched windows echo the grand arches found in the Auditorium Theatre. The swirling terra-cotta ornamentation takes inspiration from the Marquette Building, and the glass curtain wall on the west side tips its hat to 1950s modernism. Crowning the building are imposing, gargoyle-like sculptures, including owls ready to offer sage advice (or perhaps just some hoots of wisdom).

Rather unexpectedly, the grandeur one anticipates upon entering a building of this magnitude is encountered not on the ground floor but at the pinnacle, the 9th floor. Here, the impressive, sunlit Winter Garden offers a serene oasis reminiscent of an outdoor courtyard. The 8th floor accommodates practice rooms for musicians and serves as a venue for listening to rare recordings or playing the piano. On the second floor, the former library, now known as the Cultural Center, is equally captivating, featuring the world's largest Tiffany dome within its splendid chamber. The exceptional Children's Library, sprawling across 18,000 square feet, showcases wall-mounted figures by Chicago Imagist Karl Wirsum, while the walkway above the main lobby displays works by renowned Chicago artists.

Since its completion, the Library has earned its place in the Guinness Book of Records as the largest public library building globally.

Why You Should Visit:
Each floor offers special displays and collections worth exploring.
The library hosts poetry readings, art exhibitions, and boasts an unparalleled children's library.

Tip:
Make sure to ride the elevator directly to the 9th floor, where you can bask in the splendor of the exquisite glass ceiling and relish the tranquility and sunshine of the Winter Garden.
21
Fine Arts Building

21) Fine Arts Building

Constructed around 1884, this building's Romanesque rough stone base and tiered floors beneath graceful arches set the stage for the architectural rhythm along South Michigan Avenue. The arches, supported by colossal red granite columns, cleverly opened up the sturdy east wall to accommodate the Studebaker carriage showrooms that occupied the first five levels. Up above, you can spot a change in purpose as smaller windows cluster together, marking the spaces where carriages and wagons were once assembled.

When Studebaker's needs changed, enter stage right: Charles C. Curtiss, a music publisher and real estate developer. He commissioned Beman to transform the place into a pioneering arts center, complete with two theaters, offices, shops, and studios for the creative elite. The metamorphosis included a bit of vertical expansion, as the top story made way for three new ones, adorned with skylit studios. The building even played a role in the women's suffrage movement and later became a hub for Chicago's 1920s literary scene.

Step inside, and you'll navigate a labyrinth of wooden hallways teeming with history, from the light well with its charming internal balconies (aptly named Venetian Court) to Art Nouveau murals dating back to the 1900s. With ten floors of art, dance, and music studios, including the FAB Second Floor Art Gallery and the melodious PianoForte shop on the first floor, it's an artist's dreamland. While there might not be public performances or classes, art enthusiasts can revel in the open spaces and observe artists in their natural habitat. Wander through the interior courtyard, where the sweet strains of piano keys and soaring sopranos compete with hearty tenors practicing their vocal acrobatics.
22
Auditorium Building

22) Auditorium Building

A prime example of the Chicago School architectural style, the Auditorium Building is most renowned for its magnificent 4,000-seat theatre, revered for its nearly flawless acoustics and impeccable sightlines. At one point, it even inspired the legendary Modernist maestro Frank Lloyd Wright to dub it the "greatest room for music and opera in the world".

Constructed in 1889 by the esteemed duo of Louis Sullivan and Dankmar Adler, this iconic complex solidified their global reputation as pioneers in modern architectural thought. Adler's prior triumphs in theater design secured their commission for this coveted project, and the ensuing publicity catapulted Sullivan's innovative architectural principles into the spotlight.

Conceived as a permanent haven for Chicago's operatic, symphonic, and cultural events, the building's visionary design included vast, multi-use commercial spaces, a 400-room hotel, and rental offices to balance potential deficits from operating the colossal theater. It stood as a monumental civic achievement; however, within just a decade, the building had fallen into disrepair, with its lowest point marked by a transformation into a recreational center for soldiers who ingeniously repurposed the stage as a makeshift bowling alley.

Roosevelt University eventually took ownership in 1946, but it wasn't until the 1960s that the building underwent a full-scale restoration and reopened its doors. In 1989, the cultural institution marked its centenary with the grand opening of "Les Misérables". A comprehensive restoration initiative commenced in 2001, featuring extensive paint analysis to resurrect the original color patterns, intricate stenciling details, and a charming mural that once adorned the interior. In 2002, the theater's 113-year-old stage underwent removal and reconstruction, just in time to host the Bolshoi Ballet, which garnered sold-out performances and critical acclaim.

Even if you can't catch a concert, consider embarking on a tour of this historic gem!

Walking Tours in Chicago, Illinois

Create Your Own Walk in Chicago

Create Your Own Walk in Chicago

Creating your own self-guided walk in Chicago is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
The Magnificent Mile Walking Tour

The Magnificent Mile Walking Tour

The stretch of Michigan Avenue from the Chicago River to Lake Shore Drive, otherwise known as the Magnificent Mile, is regarded as one of the world’s great avenues – or Chicago’s version of Fifth Avenue. Take this self-guided walk to explore its whole stretch and surrounding area, featuring a wide selection of amazing stores/malls, world-known museums, restaurants and spectacular...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 3.2 Km or 2 Miles
Chicago Old Town Walking Tour

Chicago Old Town Walking Tour

Settled in 1850 by German immigrants, Chicago’s Old Town neighborhood is a popular destination for locals and visitors who cater to the entertainment venues, restaurants, pubs, coffee shops and boutiques – all of which have turned an area once referred to as the “Cabbage Patch” into an attraction that rivals Navy Pier, Wrigley Field and the Magnificent Mile.

Start your Old Town walking...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.6 Km or 1.6 Miles
Millennium and Grant Parks Walking Tour

Millennium and Grant Parks Walking Tour

The city of Chicago is renowned for its outdoor green spaces. One such “forever free and open” space, is called Grant Park and was established in 1844. In fact, upon foundation, it was called Lake Park, but was renamed in 1901 after the American Civil War General and United States President, Ulysses S. Grant.

Popularly referred to as “Chicago's front lawn,” this lakefront park is...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.7 Km or 1.7 Miles
Frank Lloyd Wright Architecture Tour in Oak Park

Frank Lloyd Wright Architecture Tour in Oak Park

Oak Park, located in Cook County, Illinois, just outside Chicago, made history in 1889 when Frank Lloyd Wright, one of America's most renowned architects, and his wife settled there, leaving a profound impact on the area's appearance. This village boasts the highest concentration of Wright-crafted buildings in the world - over a dozen! - making it a pivotal destination for enthusiasts to...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.2 Km or 2 Miles
Chicago Chinatown Walking Tour

Chicago Chinatown Walking Tour

Tucked away just south of the Loop, the Chinatown of Chicago was established in 1912 and is considered one of the best examples of American Chinatown. While it may be one of Chicago’s smallest neighborhoods geographically, it is big on character, colors, sights, sounds, and flavors. Here, you’ll find a wide range of unique boutiques, specialty shops, religious sights, authentic Chinese...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
Chicago Introduction Walking Tour

Chicago Introduction Walking Tour

Chicago, perched on the shores of Lake Michigan in Illinois, is a city steeped in history and urban vibrancy. Known by numerous nicknames such as the Windy City and the City of Big Shoulders, it boasts a skyline marked by towering structures. The area of today's Chicago, initially inhabited by Native American tribes, saw its first European-settled reference as "Chicagou" in 1679, a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 3.7 Km or 2.3 Miles

Useful Travel Guides for Planning Your Trip


Chicago Souvenirs: 15 Distinct Local Products to Bring Home

Chicago Souvenirs: 15 Distinct Local Products to Bring Home

One of the most fascinating cities in the U.S., if not the whole world, Chicago has no shortage of things closely associated with it, often due to their direct origin (blues, gangstership, etc.), so one might literally be spoiled for choice as to what to choose as a "piece" of Chicago to...