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
  • The Magnificent Mile
  • Chicago Water Tower
Willis Tower / Skydeck Chicago

1) Willis Tower / Skydeck Chicago (must see)

Sears, Roebuck, a Chicago icon since 1906, had outgrown its offices in the city's west area. The search for a new site would not be an easy one. Shifting the headquarters to the suburbs would not do. Company executives began to focus on the western border of the Loop district. The Loop site was finally acquired in 1970.

It was decided that the new building would be either 70 stories of 60,000 square feet each or 60 stories of 70,000 square feet each. The Sears merchandise group would be moved in, and the remaining spaces would be rented out. Plans revealed the tower was intended to be 1,450 feet high. It topped out in 1973 with over 100 floors.

In subsequent years the tower would undergo renovations and changes in ownership. Sears itself moved out to Hoffman Estates in Illinois in 1990. The building continued to be called Sears Tower until 2009 when Willis Group of London leased part of the building and obtained naming rights. Sears Tower was now Willis Tower.

The Tower was designed by architect Bruce Graham and the structural engineer Fazlur Rahman Khan. The basic design concept was nine square "tubes" bundled in a 3x3 matrix having a square base with 225-foot sides. The Tower was the first building to use this innovative design, both efficient and economic.

The Willis Tower Observation deck on the 103rd floor, called Skydeck, is 1,353 feet above street level. It opened to the public on June 22, 1974. There is a second observation deck on the 99th floor. Retractable glass balconies were installed in a renovation of the Skydeck in 2009. The balconies are all-glass boxes that project up to four feet from the sides of the Tower. Elevators reach the top in 60 seconds.

Every year, almost two million tourists visit Skydeck, the highest in the United States, and enjoy breathtaking views spanning 50 miles and four states on a clear day.
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)

The Chicago Academy of Design was started in a studio on Dearborn Street in 1866. It was a group studio and gallery of 35 artists. The organization of the studio was modeled after European art academies, such as England's Royal Academy. A free school with its gallery was attached to the Academy. The Academy received its charter in 1867.

The Academy building was destroyed in the Great Chicago Fire of 1871. Some members of the Academy then founded the Chicago Academy of Fine Arts. In 1882 the Academy of Fine Arts changed its name to the Art Institute of Chicago.

The Art Institute building at 111 South Michigan Avenue is a Beaux-Arts creation by Shepley, Rutan, and Coolidge, a successful architecture firm based in Boston. The western entrance of the Institute is guarded by two large bronze lions made by sculptor Edward Kemeys. The lions are often dressed in the jerseys of winning Chicago sports teams. At Christmas time they wear wreaths.

In May 2009, the Art Institute opened its new Modern Wing. This is a 264,000-square-foot annex designed by Italian architect Renzo Piano. The Modern Wing houses the Institute's early 20th-century European Art represented by Pablo Picasso, Henri Matisse, Rene Magritte, etc., and the Bergman Collection of Surrealist Art.
Crown Fountain

4) Crown Fountain

In 1997 Grant Park by the Illinois Central Railroad was made a part of Millennium Park. The new park was conceived as a venue for the works of world-famous architects, artists, designers, and planners. In December 1999, the Lester Crown family volunteered to sponsor a water feature in Millennium Park.

The Crowns actively participated in the design and engineering of the Fountain. They were looking for modern work, animated and interactive. Their commission was awarded to Spanish artist Jaume Plensa. In the Crown Fountain, Plensa created an eternal dualist waterwork that would still be life-like in Chicago winters.

The Fountain shows the artist's penchant for dualism with two fifty-foot monolithic glass brick towers facing each other. Between the two towers is a black granite reflecting pool. The towers display digital videos on their inside faces. Waterspouts from nozzles on the outside faces while water cascades on each side.
Cloud Gate

5) Cloud Gate (must see)

The Cloud Gate is a public sculpture, the centerpiece of AT&T Plaza at Millennium Park, constructed between 2004 and 2006. It was created by the Indian-born British sculptor Anish Kapoor, well-known for his large-scale outdoor works, including several with highly reflective surfaces. The Cloud Gate was his first public outdoor work in the United States and is considered his most famous one.

The Cloud Gate is made entirely of stainless steel; 168 plates are welded together and polished to conceal the seams. The sculpture stands three stories high, measuring 66 feet long, 33 feet high, and 42 feet wide, and weighing 100 tons. It has been lovingly dubbed by the locals as "The Bean," although the design has been inspired by a drop of mercury. Concave at the bottom, it creates a spectacular fun mirror effect for those walking underneath, reflecting distorted images of the Chicago skyline.

At the time, before its installation, the sculpture was subject to controversy among experts, some of whom believed it could not be implemented because of the technical difficulties associated with its construction, assembly, upkeep, and maintenance. Although a feasible solution was eventually found, the project fell behind schedule and was still unfinished by the time Millennium Park was opened in 2004. The Cloud Gate was completed and formally dedicated only on May 15, 2006, and has since enjoyed great acclaim both at home and abroad.
Millennium Park

6) Millennium Park (must see)

Millennium Park is a public park in the Loop community area of Chicago. Originally, it was intended to celebrate the third Millennium, hence the name. Bounded by Michigan Avenue, Randolph Street, Columbus Drive, and East Monroe Drive, this is a prominent civic center near the city's Lake Michigan shoreline that covers a 99 000 square meters section of northwestern Grant Park. The latter is linked to Millennium Park by the BP Pedestrian Bridge and the Nichols Bridgeway.

The park features a variety of public art, outdoor spaces, and venues. In 2015, it became the location of the city's annual Christmas tree lighting. Millennium Park is free to enter and is home to multiple attractions, such as the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain, the Lurie Garden, and others. Because it sits atop parking garages and the commuter rail Millennium Station, the park is considered the world's largest rooftop garden and has received awards for its accessibility and green design.

In 2017, Millennium Park was the top tourist destination in Chicago and the American Midwest and was placed among the top ten in the United States with 25 million annual visitors.
DuSable Bridge

7) DuSable Bridge

Jean Baptiste Pointe du Sable, commonly regarded as the "Father of Chicago," was thought to be a native of the French colony Saint Dominique in the Caribbean. He is credited with being the first settler in the area of Chicago. His name is on schools, a museum, a park, and the DuSable Bridge spanning the Chicago River.

The bascule-style bridge was erected in 1928. It was part of a plan to link the south and north side parks of Chicago with Grand Boulevard. On the north, it connects with the 1780s homestead site of Jean Baptiste du Sable. The south side ends at the early 19th-century location of Fort Dearborn.

Also called the Michigan Avenue Bridge, the DuSable Bridge is a double-leaf, double deck, fixed counterweight, trunnion bascule bridge. It has a roadway on both levels. Edward H. Bennett was the consulting architect of the project, and William A. Mulcahy was the chief engineer.

Sculptures in the bridge tender houses by artist Henry Hering depict Discoverers, Pioneers, the 1812 Battle of Fort Dearborn, and Regeneration after the Great Fire of Chicago. The bridge also has 28 flagpoles for flags of the United States, Illinois, and Chicago and other banners as needed.
The Magnificent Mile

8) The Magnificent Mile (must see)

Michigan Avenue, and particularly the upscale section between the Chicago River and Oak Street in the Near North Side, known as The Magnificent Mile, is Chicago's largest shopping destination.

As a premier commercial district and home to an array of mid-range and high-end shops, restaurants, and hotels, the street caters primarily to tourists and the affluent. Many of the world's leading retail stores populate the avenue, including luxury department stores Bloomingdale's, Neiman Marcus, Saks Fifth Avenue, and Nordstrom. It is also home to three urban shopping centers: Water Tower Place, The Shops at North Bridge, and 900 North Michigan Shops.

Renowned and critically acclaimed restaurants, located along The Magnificent Mile, provide a variety of dining options. However, if you come to Chicago specifically for the famous local pizza, then you should check out, among other locations, Gino's East and Lou Malnati's, which offer some of the best Chicago-Style deep dish pizza experiences in the city.

There are also plenty of great architectural marvels along The Magnificent Mile. InterContinental Hotel is a stylish and historic building. The Chicago Water Tower is one of the few structures that survived the Great Chicago Fire of 1871 and represents a monument to that event. The Wrigley Building skyscraper with its two towers in an elaborate style built between 1920-1924, and the Tribune Tower, a 36-floor neo-Gothic skyscraper, are also located in the district.
Chicago Water Tower

9) Chicago Water Tower

The great Chicago Water Tower is located at 806 North Michigan Avenue in the Magnificent Mile district. It sits in the small Jane M. Byrne Plaza. The Tower was made to house a huge water pump used to draw water from Lake Michigan. These days, The Water Tower serves as an art gallery for photographers and filmmakers.

The Tower was created in 1869 by architect William W. Boyington. It is almost 183 feet high construction, built of yellow Lemont limestone. It was used together with the Chicago Avenue Pumping Station to control water surges and assist in firefighting. Oscar Wilde once said, "it was a castellated monstrosity with pepper boxes stuck all over it."

It is thought that the Water Tower's castled style inspired the design of the White Castle restaurants. The Chicago Water Tower was named an American Water Landmark in 1969. The tower was featured in the reality television finales of The Amazing Race 6 and The Amazing Race 29.

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.
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
Loop District Architecture Walking Tour

Loop District Architecture Walking Tour

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...  view more

Tour Duration: 3 Hour(s)
Travel Distance: 4.6 Km or 2.9 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
University of Chicago Walking Tour

University of Chicago Walking Tour

Founded in 1890, the University of Chicago is among the world’s most prestigious educational institutions. As of 2020, the University’s students, faculty and staff have included 100 Nobel laureates, giving it the fourth-most affiliated Nobel laureates of any university.

Set in the heart of Chicago’s famous eclectic neighborhood, Hyde Park, the campus is worth a visit as it offers a...  view more

Tour Duration: 2 Hour(s)
Travel Distance: 2.5 Km or 1.6 Miles
Chicago Navy Pier Walking Tour

Chicago Navy Pier Walking Tour

Additional to scenic views of the lake, the boats, and the city skyline, the Navy Pier offers a variety of attractions on the waterfront – for kids as well as adults – that draw nearly ten million people annually, making this Chicago's most visited spot. Yes, some may see it as a “tourist trap”, but it is worth the time and money to spend some time here, so take this self-guided walk...  view more

Tour Duration: 1 Hour(s)
Travel Distance: 1.0 Km or 0.6 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

Useful Travel Guides for Planning Your Trip

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