Chicago Introduction Walking Tour, Chicago

Chicago Introduction Walking Tour (Self Guided), Chicago

Sitting on the shore of Lake Michigan in the U.S. State of Illinois, Chicago has had many nicknames throughout its history, including the Windy City, Chi-Town, Second City, and the City of the Big Shoulders referring to the numerous towers and high-risers that punctuate its skyline.

Prior to the Europeans, the area of today's Chicago was successively inhabited by various Native American tribes who, after several victorious military campaigns by the United States, were removed from their land. The first known reference to the territory as "Chicagou" dates back to 1679, and stems from a French rendering of the indigenous Miami-Illinois word “shikaakwa” which means wild garlic or onion, reportedly once grown here in large quantities. The first non-indigenous permanent settler in Chicagou was explorer of African and French descent, Jean Baptiste Point du Sable, who arrived in the 1780s and is commonly regarded as the "Founder of Chicago".

The city was incorporated in 1837. It grew rapidly in the mid-19th century as an important transportation hub between the eastern and western United States. During World War I and the 1920s, a major expansion in the local industry attracted migrants. Simultaneously, the Prohibition era made Chicago notorious with the gangsters like Al Capone battling law enforcement and each other. After the Great Depression pause, Chicago's heavy industry boomed again with hundreds of thousands of African Americans coming from the South to work in the steel mills, railroads, and shipping yards during World War II.

Over the years, Chicago made eminent contributions to urban planning and gave rise to new construction styles such as, Chicago School architecture, the City Beautiful Movement, and steel-framed skyscrapers. A thriving hub of international trade and commerce, the city abounds in vibrant tourist sights and has been repeatedly chosen among the "Top Ten Cities in the United States" to visit.

The local landmarks are numerous and include, among others, the likes of Millennium Park (complete with the reflective Cloud Gate sculpture in AT&T Plaza, and the two tall glass sculptures making up the Crown Fountain), the Magnificent Mile (renowned for its upscale shopping), the Art Institute of Chicago (home to the noted Impressionist and Post-Impressionist works), and the Willis Tower (formerly named Sears Tower), to mention but a few.

If you wish to get a sense of today's Chicago and explore its top attractions in more detail, take our self-guided introductory walk!
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Chicago Introduction Walking Tour Map

Guide Name: Chicago Introduction Walking Tour
Guide Location: USA » Chicago (See other walking tours in Chicago)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 9
Tour Duration: 2 Hour(s)
Travel Distance: 3.5 Km or 2.2 Miles
Author: doris
Sight(s) Featured in This Guide:
  • Willis Tower - Skydeck Chicago
  • Rookery Building
  • Art Institute of Chicago
  • Crown Fountain
  • Cloud Gate
  • Millennium Park
  • DuSable Bridge
  • Magnificent Mile
  • Chicago Water Tower
Willis Tower - Skydeck Chicago

1) 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

2) 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.
Art Institute of Chicago

3) Art Institute of Chicago (must see)

Perched atop a grand set of stone steps and guarded by its iconic lion statues, you'll discover the Midwest's most extensive art museum. Within the colossal Beaux-Arts structure, this institution proudly displays an expansive array of artworks from diverse regions worldwide. It is notably enhanced by a comprehensive assortment of modern and contemporary pieces featured in the Modern Wing, an architectural marvel designed by the renowned Italian architect, Renzo Piano.

Organized chronologically, the extensive European Collection spans from the Middle Ages to 1950, encompassing a substantial assortment of Renaissance and Baroque art and sculptures. Yet, its primary attraction lies in its nearly 400 Impressionist and Post-Impressionist paintings. Meanwhile, the American Arts collection comprises approximately 5,500 paintings and sculptures spanning from the 1600s to 1950. Additionally, the loans from the Terra Foundation collection encompass paintings and works on paper, as well as a diverse range of decorative arts, including furniture, glass, and ceramics from the 18th century to the present (notably, the silver collection stands out). Among the must-see attractions are beloved Chicago gems such as the Thorne Miniature Room and Chagall's remarkable stained-glass creation, "American Windows".

Why You Should Visit:
The diverse collection encompasses paintings, drawings, sculptures, and designs that span from ancient times to the contemporary world. Visitors will have the opportunity to explore a rich array of artworks from various eras and regions, including Greek, Roman, Byzantine, European, Asian, African, and Native American art. Additionally, you can delve into the museum's extensive and comprehensive photography collection, making it a truly enriching cultural experience.
Crown Fountain

4) Crown Fountain

To the south of Tribune Plaza, you'll encounter Crown Fountain, a striking installation designed by the renowned Spanish architect Jaume Plensa. Comprising two impressive 50-foot (15.2-meter) glass towers that face each other across a granite plaza, this fountain is a unique attraction. Beneath the surface of the glass blocks, LED screens display a rotating gallery of close-up images featuring 1,000 Chicago residents. These individuals, drawn from various communities within the city, were asked to simulate blowing on a feather while being filmed. Now, when their digital representations purse their lips, water playfully spouts from their mouths, bringing joy to playful children. In the summertime, it transforms into a popular splash park, but even during Chicago's winters, the fountain retains its lifelike charm.

The atmosphere surrounding Crown Fountain is infectious, drawing people from diverse backgrounds and fostering an extraordinary sense of community. It's the kind of place that transcends social boundaries and unites people, if only for a brief moment. The sight of strangers-turned-friends sharing laughter as they dodge the dancing water spouts is bound to bring a smile to your face.

Why You Should Visit:
Whether you want to bask in the sun, enjoy a picnic, or simply take a leisurely stroll, everything is readily available here. The area is consistently well-maintained, with crystal-clear water and meticulously kept grounds. It's evident that the city takes great pride in preserving the beauty of this location, and this commitment shines through in every aspect.
Cloud Gate

5) Cloud Gate (must see)

Situated at the heart of AT&T Plaza within Millennium Park, Cloud Gate was created during the years 2004 to 2006, under the artistic vision of Anish Kapoor, an Indian-born British sculptor renowned for his large-scale outdoor artworks, many of which feature highly reflective surfaces. This sculpture marked Kapoor's inaugural foray into public outdoor art in the U.S., standing as his most iconic creation.

Crafted entirely from stainless steel, this monumental work meticulously joined 168 plates, expertly polished to conceal any visible seams. Towering over three stories tall, it spans 66 feet in length, 33 in height, and 42 in width, with a weight of 100 tons. Locals affectionately refer to it as "The Bean", though its design was actually inspired by the shape of a mercury droplet. With its concave underside, it conjures a funhouse mirror effect for those who venture beneath, reflecting captivatingly distorted images of the Chicago skyline.

Before its installation, Cloud Gate stirred controversy among experts, some of whom doubted its feasibility due to the technical challenges related to construction, assembly, maintenance, and upkeep. While a viable solution was eventually devised, the project experienced delays and was still unfinished when Millennium Park opened in 2004. The formal dedication of Cloud Gate took place on May 15, 2006, following its completion, and it has since garnered widespread acclaim both domestically and internationally.

Why You Should Visit:
Taking a selfie in front of this captivating artwork, which mirrors the surrounding skyline, has become an iconic Chicago souvenir.
Millennium Park

6) Millennium Park (must see)

In 2004, when Anish Kapoor's colossal, gleaming Cloud Gate sculpture, the lively fountains, the captivating Crown Fountain, and a Disney-esque music pavilion all came together in this park, they quickly won the affection of both Chicagoans and tourists. This public space, which cost $250 million more than planned and opened four years later than scheduled, stands out as Chicago's most dazzling, showcasing contemporary architecture and design. Paul Goldberger, the architecture critic for The New York Times, hailed it as "one of the great new models for a kind of urban park." It has been embraced by locals and visitors alike and is widely considered the most impressive public project in Chicago since the 1893 World's Fair.

The park's origins trace back to a moment when Mayor Richard M. Daley conceived of it while sitting in his dentist's chair across the street, gazing at the sea of parking lots and railyards that occupied the site until the late 1990s. The initial design, created by the globally renowned Skidmore, Owings and Merrill firm based in Chicago, adhered to the traditional style of Grant Park, featuring formal fountains and gardens. However, private donors who had pledged to supplement public funding for the park's construction rejected this design as too conservative. Cindy Pritzker, a prominent Chicago philanthropist and the spouse of the late Jay Pritzker, the founder of the Hyatt hotel chain and the esteemed Pritzker Prize in architecture, eventually persuaded Frank Gehry (a previous Pritzker Prize laureate) to design the park's central pavilion, along with a bridge leading to the lake across Columbus Avenue. Gehry's involvement attracted other exceptional talents to the project, resulting in an impressively diverse yet cohesive masterpiece.

The star attraction undoubtedly lies in Gehry's remarkable Jay Pritzker Pavilion, featuring striking ribbons of stainless steel soaring 40 feet into the sky, resembling petals enveloping the music stage. Other notable elements include the Harris Theater for Music and Dance, offering an indoor option for performing arts enthusiasts, the McCormick Tribune Ice Rink, and the Lurie Garden, a year-round delight.
DuSable Bridge

7) DuSable Bridge

Chicago boasts one of the largest collections of movable bridges in the world, with trunnion bascules being the predominant type. This particular bridge, well-suited for its prominent and bustling location, elegantly spans the river without any protruding superstructures, maintaining a generous, navigable channel. Its construction held paramount importance in the 1909 Plan of Chicago, serving as a catalyst for the rapid revitalization of real estate along North Michigan Avenue. Drawing inspiration from the design of Paris's Alexander III Bridge (1900), it features four corner pylons, decorative abutments, a gracefully flat arch profile, and seamlessly integrated embankments.

The forty-foot pylons, serving as functional operator houses, are adorned with sculptural reliefs narrating key events in Chicago's history. These include the explorations of Marquette and Joliet, the establishment of the city by trader Jean Baptiste Point du Sable, the Fort Dearborn Massacre of 1812, and the city's reconstruction following the devastating Great Chicago Fire of 1871. A commemorative plaque marks the site of the fort at the southern end of the bridge. Additionally, the southwest structure now houses a museum operated by the Friends of the Chicago River, open seasonally, providing visitors with the opportunity to observe the inner workings of the bridge's gears responsible for its opening and closing.
Magnificent Mile

8) Magnificent Mile (must see)

Strolling down the expansive stretch of Michigan Avenue north of the Chicago River is a must-do for nearly every visitor to the city. Known as one of the world's most renowned shopping districts, the Magnificent Mile boasts a rich assortment of mainstream retailers, major department stores, and shopping centers. Even if you aren't inclined to shop, there's much to captivate your interest here. The southern end of this bustling strip is anchored by the iconic Wrigley Building skyscraper, featuring two elaborately designed towers constructed between 1920 and 1924, as well as the Tribune Tower, a 36-floor neo-Gothic skyscraper. At the northern terminus stands the impressive 100-storey John Hancock Center, with the famous Water Tower situated in between.

Apart from being one of Chicago's premier spots for people-watching, the Magnificent Mile is also a haven for food enthusiasts, offering a wide array of dining choices, including renowned and critically acclaimed restaurants. However, if you come to Chicago with a specific craving for the city's famous local pizza, be sure to explore Gino's East and Lou Malnati's, among other locations, as they provide some of the finest Chicago-Style deep dish pizza experiences available in the city.
Chicago Water Tower

9) Chicago Water Tower

The intersection of Michigan Avenue and Pearson Street in Chicago serves as a fascinating meeting point between the city's historical legacy and its contemporary identity. Here, the towering Water Tower Place, long considered the pinnacle of Chicago shopping, stands in contrast to one of the few remaining remnants of Old Chicago: the historic Water Tower. This unique limestone structure, adorned with peculiar turrets that Oscar Wilde humorously described as resembling "a castellated monstrosity with pepper boxes stuck all over it," was constructed in 1869 to accommodate a standpipe, regulating water pressure from the nearby Pumping Station.

Both of these edifices played pivotal roles in the city's ambitious endeavor to provide safe drinking water to its burgeoning population. It wasn't until 1900, when the city reversed the flow of the Chicago River to redirect its waste southward toward St. Louis, that this goal was truly achieved. Remarkably, these buildings withstood the devastating Great Fire of 1871 that consumed much of downtown Chicago, becoming enduring symbols of the city's resilience and remaining among its most iconic landmarks.

Today, the interior of the Water Tower has been repurposed to host temporary photo exhibitions centered around Chicago themes, while the Pumping Station houses the Chicago Water Works Visitor Center, where visitors can obtain a wealth of maps, brochures, and information about the latest cultural events happening throughout the city. Notably, a recent addition to the Pumping Station is a 270-seat theater that showcases productions by the Lookingglass Theatre Company.

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.
Loop District Architecture Walking Tour

Loop District Architecture Walking Tour

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Tour Duration: 3 Hour(s)
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Chicago Old Town Walking Tour

Chicago Old Town Walking Tour

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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

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Tour Duration: 2 Hour(s)
Travel Distance: 2.7 Km or 1.7 Miles
Chicago Chinatown Walking Tour

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Tour Duration: 1 Hour(s)
Travel Distance: 1.7 Km or 1.1 Miles
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
Frank Lloyd Wright Architecture Tour in Oak Park

Frank Lloyd Wright Architecture Tour in Oak Park

Oak Park is a village in Cook County, Illinois, adjacent to Chicago. Architect Frank Lloyd Wright and his wife settled in Oak Park in 1889, and his work heavily influenced local architecture and design, including the Frank Lloyd Wright Home and Studio. Oak Park is home to the world’s largest collection of buildings designed by Frank Lloyd Wright. View the exteriors of nearly a dozen of...  view more

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

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