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: 12
Tour Duration: 3 Hour(s)
Travel Distance: 4.6 Km or 2.9 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Aqua (skyscraper)
  • Chicago Theatre
  • Chicago City Hall & County Building
  • Civic Opera House
  • Union Station
  • Willis Tower - Skydeck Chicago
  • Rookery Building
  • Marquette Building
  • Fisher Building
  • Harold Washington Library Center
  • Fine Arts Building
  • Auditorium Building
Aqua (skyscraper)

1) 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.
Chicago Theatre

2) 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.
Chicago City Hall & County Building

3) 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.
Civic Opera House

4) Civic Opera House

The elegant residence of both the Lyric Opera of Chicago and the Joffrey Ballet exudes grandeur. Its interiors boast pink-and-gray Tennessee-marble floors, pillars adorned with intricately carved capitals, sparkling crystal chandeliers, and a magnificent staircase leading to the second floor. Crafted by the architectural firm Graham, Anderson, Probst & White, this colossal edifice seamlessly blends opulent Art Deco elements with Art Nouveau influences, all while incorporating musical motifs into its design. With a seating capacity of 3,563, it stands as the second-largest opera auditorium in North America, just behind New York City's Metropolitan Opera House.

Conceived as a tribute to both culture and commerce, this building was finalized in 1929 and represents the final major real estate project undertaken by Samuel Insull, Chicago's magnate of traction and utilities. A grand two-story portico runs the entire length of the east facade, giving it the appearance of a colossal armchair when viewed from the river. Pediments mark the entrances to the theaters, with the smaller one having been converted to support space. Inside, the Grand Foyer soars to a height of forty feet and features a color scheme chosen by Jules Guerin, the mastermind behind the theater's fire curtain.

Why You Should Visit:
Here, you can revel in turn-of-the-century charm while enjoying high art at reasonable prices. The building's size ensures that last-minute seating is often available, and its impeccable acoustics enhance the overall experience.

Don't forget to explore the fascinating mini-museum downstairs, which always offers something of interest. Additionally, consider treating yourself to a backstage tour to gain insights into the inner workings of an opera production.
Union Station

5) Union Station

You can experience the grandeur of the golden age of train travel at Union Station, one of the few remaining majestic American railroad stations. This station was a crucial component of Burnham's 1909 Plan of Chicago, designed to spearhead West Loop development. In the 1940s and 1950s, over 100,000 travelers strolled across the pink marble floors of the Great Hall daily, or rested beneath its airy, vaulted ceilings on wooden benches. Today, that number has significantly reduced, and many passengers skip the hall, opting to buy tickets onboard the trains. Nonetheless, one of the highlights of the decade-long improvement project is the restoration of the Great Hall's iconic staricases and massive skylight which, according to engineers, enhances natural light by about 50 percent.

The eight-story office tower, positioned well behind the base and nearly invisible from the street, was originally intended to reach twenty stories. Another noteworthy aspect is the double "stub end" tracks, the only ones in the United States where northbound and southbound tracks for different railroads terminate at the same point.

Upon its completion, Union Station was lauded as a remarkable achievement in railroad facility planning. Today, this monumental Neoclassical station serves as the last surviving railroad terminal that nearly every cross-country Amtrak train passes through.
Willis Tower - Skydeck Chicago

6) Willis Tower - Skydeck Chicago (must see)

Designed by Skidmore, Owings & Merrill in 1974, the former Sears Tower stood as the tallest skyscraper globally until 1996. Recommended by the readers of the Chicago Tribune as one of the "7 wonders of Chicago", this impressive structure stands tall at 1,730 feet, spanning 110 stories. While it may have yielded its title and embraced a new name, the fascination of the Skydeck on the 103rd floor remains unmatched. On clear days, it provides breathtaking vistas encompassing Illinois, Michigan, Wisconsin, and Indiana.

The journey in the elevator, lasting a mere 70 seconds, is transformed into an exhilarating experience through video monitors. Within the observatory, interactive exhibits breathe life into Chicago's visionaries, entrepreneurs, architects, musicians, and sports icons. Additionally, computer kiosks, available in six languages, aid international travelers in discovering Chicago's most sought-after destinations. Yet, for many visitors, the ultimate highlight is stepping onto the Ledge, a glass enclosure protruding 4.3 feet from the building, creating the illusion of being suspended 1,353 feet above the ground.

Despite occupying an entire city block and boasting over four million square feet of interior space, the tower was remarkably constructed in just three years. Its innovative design featured nine massive steel "tubes" of varying lengths, bundled together to provide both strength and flexibility. The concept for these distinct levels is said to have originated from the observation of someone shaking cigarettes out of a pack. Initially intended to accommodate up to 13,000 employees of the department store Sears Roebuck & Co., the tower changed hands in 1989 when it was sold to three property developers and is now home to a diverse range of commercial tenants. Remarkably, it houses one hundred elevators and 16,000 windows, all of which are thankfully equipped with automatic window-cleaning systems.

Before deciding to ascend, it is advisable to check the visibility ratings, either on your phone or at the security desk. If visibility is less than five miles, it's best to plan your visit for another time.
Rookery Building

7) 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.
Marquette Building

8) 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.
Fisher Building

9) 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.
Harold Washington Library Center

10) 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.

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.
Fine Arts Building

11) 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.
Auditorium Building

12) 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!

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