Last updated on March 1, 2024.

The Chicago Loop is the central business district of Chicago and one of three community areas making up the heart of the city.

L tracks in the Chicago Loop
L tracks in the Chicago Loop

 

What Exactly Is the Chicago Loop?

According to locals, the strict boundaries of the Chicago Loop is the area that falls within the L tracks above Wells Street, Van Buren Street, Wabash Avenue, and Lake Street. If you follow the community area definition, the boundaries of the Loop are the Chicago River to the north and west, Lake Michigan to the east, and Roosevelt Road to the south.

The Loop contains Chicago City Hall, numerous government buildings, and several architecturally important skyscrapers. You’ll also find lots of great shopping, the city’s theatre district, and some great museums and parks. All in all, the Chicago Loop is a great place to explore for all types of interests.

 

Organization of This Post on the Chicago Loop

For this post, we’ll use the community area boundaries. It covers a walking tour of the Chicago Loop in the area west of Michigan Avenue. I’ll start at State and Lake, walk south down State Street to Van Buren Street, and come back north up Dearborn Street. After visiting Daley Plaza, I’ll continue south down LaSalle Street to Jackson Boulevard. From there, I’ll swing over to the Willis Tower (which according to the strict definition isn’t in the Chicago Loop). At the end, we’ll take a quick tour of Printer’s Row. There’s more I’d like to cover in the Loop, and I’ll try to get to it on my next trip to Chicago.

 

State Street

State Street, that great street” is one of the most famous streets not only in the Loop but in Chicago in general. It was the city’s first major shopping street and runs through the heart of the theatre district.

State Street in Chicago
State Street

State Street started out as a muddy unpaved street in the middle of the 1840s. That all changed when businessman Potter Palmer (1826-1902) convinced Marshall Field (1834-1906) and Levi Leiter (1834-1904) to move Field, Leiter & Company (the future Marshall Field & Company) to the corner of State and Washington in 1868. Palmer himself built the luxurious Palmer House hotel nearby in 1870. Soon after, in the early 1900s, State Street became Chicago’s premier shopping destination and was mentioned in the song “Chicago“, written by Fred Fisher (1875-1942) in 1922.

State Street in the Chicago Loop
State Street

After being eclipsed by the Magnificent Mile for luxury shopping in the second half of the 20th century, various revitalization projects have taken place. For example, in 1979, State Street was pedestrianized except for buses but reopened to traffic on November 15, 1996. Since then, it has seen its most important department stores change ownership and names, but it’s still a “great street” with plenty of prestige.

 

Chicago Theatre

A good place to start exploring State Street is in front of the legendary Chicago Theatre, whose marquee on State Street is an iconic symbol of the city. It originally opened in 1921 and has a capacity of 3,600. The theatre offers daily tours for those who want a behind the scenes look.

Chicago Theatre in Chicago, Illinois
Chicago Theatre

The Chicago Theatre was the first cinema venue of its kind in America, and the façade was designed to resemble the Arc de Triomphe in Paris. The architects were Rapp and Rapp. After several years of success, the theatre fell into disrepair but continued to serve as a cinema until it closed in 1985. The Chicago Theatre was saved from demolition in the 1980s and renovated to modern standards. Currently, the theatre is used for mostly musical and comedy acts.

 

Chicago Theatre Tour

In my entire life, I had only entered this building twice for comedy shows. I appreciated the grandeur of the entire building but never really knew the history of it. That’s why I decided to take a tour.

Chicago Theatre on State Street in Chicago, Illinois
Chicago Theatre

Tours of the theatre are available via the official website. They run every Friday and Saturday at noon for US$20 (as of July 2023). Tickets are available online or at the box office on a first come, first served basis. When I visited, the tour lasted about an hour and I purchased my tickets at the box office.

 

Beginning of the Tour

Our tour began in the lobby with a very enthusiastic employee talking about the origins of the theatre and pointing out some unique architectural features. It was very interesting to hear how the theatre operated on a daily basis and the innovative marketing techniques used to attract moviegoers. From there, the tour continued to the luxury boxes where we were given a view from the best seats in the house.

Lobby of the Chicago Theatre on State Street
Lobby
Staircase of the Chicago Theatre on State Street
Staircase
Corridor of the Chicago Theatre on State Street in the Loop
Corridor
Luxury Boxes at the Chicago Theatre on State Street
Luxury Boxes

Next it was up to the balcony to get an incredible look at the murals of Greek gods painted on the walls. We also learned about the fine details that went into designing the auditorium.

Balcony of the Chicago Theatre on State Street
Balcony
Balcony of the Chicago Theatre on State Street
Balcony
Auditorium of the Chicago Theatre on State Street
Auditorium paintings

As we sat in the seats, the guide told us how the owners of the theatre, Balaban and Katz, used several tons of sandbags to convince the public of the safety of the balcony. She also pointed out the projector room that’s mainly unused today, and explained how ushers would use a complex set of hand signals to indicate empty seats for movie patrons. Balaban and Katz boasted that they had the most efficient ushers in the world.

Projector of the Chicago Theatre on State Street
Projector

 

Main Floor of the Chicago Theatre

Next, it was down to the main floor where we had a good look at the original Wurlitzer organ that was installed with the building. It’s the oldest surviving Wurlitzer in Chicago. There were actually two organs that were both played during silent films. The organists became celebrities, often overshadowing the films themselves.

Wurlitzer organ at the Chicago Theatre on State Street
Wurlitzer organ

We walked up the stage and had a breathtaking view of all the seats in the auditorium. I could only imagine what it was like for a performer with a full house and lights blaring in their face.

View from the stage at the Chicago Theatre on State Street
View from the stage

The last leg of the tour took us backstage and up a staircase where every single performer has autographed the walls since 1986. Frank Sinatra started the tradition when he performed for the grand re-opening of the Chicago Theatre on 15 September of that year. The staircase led to a modest dressing room as compared to the rest of the building.

Autographs at the Chicago Theatre on State Street
Backstage autographs
Dressing room at the Chicago Theatre on State Street
Dressing room
Dressing room at the Chicago Theatre on State Street
Dressing room

 

My Thoughts on the Chicago Theatre Tour

I highly recommend the tour of the Chicago Theatre to both visitors and residents. The building is a living piece of Chicago history that tells a lot about the city’s personality and culture. I also recommend seeing a show if possible.

 

Page Brothers Building

Next door to the Chicago Theatre, at the corner of State and Lake, is the Page Brothers Building. It was completed in 1872, shortly after the Great Chicago Fire of 1871, by architect John Mills Van Osdel (1811-1891). The building was originally five stories high but a sixth story was added when it was remodeled in 1902. The Page Brothers Building features the city’s last remaining cast iron front.

Page Brothers Building on State Street in Chicago, Illinois
Page Brothers Building

 

ABC Building

Across the street from the Chicago Theatre is the ABC Building. Formerly State-Lake Theatre, it opened on March 17, 1919, as a vaudeville theatre behind an office building designed by Rapp and Rapp. It became part of the Balaban and Katz chain in 1938, offering live acts and movies until 1941, when it switched to movies only.

ABC Building on State Street in Chicago, Illinois
ABC Building

State-Lake Theatre closed permanently on June 28, 1984, and was converted into studios and offices for WLS-TV, the local ABC affiliate. The façade was restored to its 1920s appearance, without the marquee and ticket booth. The Oprah Winfrey Show was once filmed there, and local newscasts for ABC-7 Eyewitness News began in 2006.

ABC Building
ABC Building

 

Gene Siskel Film Center

South of the ABC-7 studios is the Gene Siskel Film Center. It presents a selection of international, independent, and classic films in its two state-of-the-art theatres. It also hosts various film festivals throughout the year. The center was founded as the Film Center of the School of the Art Institute of Chicago in 1972 and renamed for film critic Gene Siskel (1946-1999). It moved to its current location on State Street in June 2001.

Gene Siskel Film Center
Gene Siskel Film Center

 

Oriental Theatre (Nederlander Theatre)

Turning west down Randolph Street for a moment is the former Oriental Theatre. It opened on May 8, 1926, and was designed by Rapp and Rapp. It originally presented motion pictures and stage shows, but fell into disrepair and was eventually closed to the public in 1981. Restoration began in 1996 and it reopened in 1998 as the Ford Center for the Performing Arts. It was renamed the James M. Nederlander Theatre in February 2019 and continues as a venue for live stage musicals. One interesting tidbit of information is that the Oriental Theatre was built on the site of the Iroquois Theater, where 600 people died in a fire in 1903.

Oriental Theatre in Chicago
Oriental Theatre

 

Marshall Field & Company Building

Back on State Street is the start of the shopping district. First is the Marshall Field & Company Building, which occupies the block between Randolph and Washington. It housed the flagship location of iconic department store Marshall Field & Company from 1902 to 2006. Since then, it has been owned by Macy’s. The building was designated a National Historic Landmark on June 2, 1978.

Marshall Field & Company Building in Chicago
Marshall Field & Company Building

The Marshall Field & Company Building was designed by Daniel Burnham (1846-1912) and stands 13 stories high. Construction took place in stages between 1901 and 1906. Sections were added in 1906, 1907, and 1914. With 73 acres of floorspace, the building was once the largest store in the world and is still the second largest.

The building’s interior is impressive. There are several floors to explore and some interesting features including three atria. The atrium on the southwest corner is covered by a 6,000 square foot Tiffany ceiling that contains 1.6 million pieces of iridescent glass. It’s the largest glass mosaic of its kind in the world. The atrium on the northwest corner is covered by a skylight 13 stories high.

Northwest atrium at the Marshall Field & Company Building in Chicago, Illinois
Northwest atrium

 

Marshalll Field & Company Origins

Marshall Field & Company was founded at 137 Lake Street in 1852 by Potter Palmer (1826-1902) as P. Palmer & Company. He entered into a partnership with Marshall Field (1834-1906) and Levi Leiter (1834-1904) on January 4, 1865, and the company became Field, Palmer, Leiter & Company. Palmer withdrew two years later, and it was renamed Field, Leiter & Company.

After moving to the corner of State and Washington in 1868, the store burned down during the Great Chicago Fire of 1871. As the fire quickly spread through the city, Leiter decided to load as much of the most valuable merchandise as possible onto wagons and take them to his home for storage. This allowed the store to reopen at a temporary location at State and 20th Street just a few weeks later. In April 1872, Field & Leiter moved to an unburned building at Madison and Market (now Wacker Drive).

In October 1873, the store reopened at its former location at State and Washington in a new five story building. That building was also destroyed by fire in November 1877, and the store moved to a temporary location where the Art Institute of Chicago now stands. A new six story building went up at their State and Washington location, opening in April 1879.

In January 1881, Field bought out Leiter who retired from the business to concentrate on real estate investments. The six story building was demolished in 1892 and a new building designed by Daniel Burnham opened the next year in time for the World’s Columbian Exposition. Burnham also designed the current building, which partially opened in 1902.

Marshall Field & Company Building
Marshall Field & Company Building

 

Post-Marshall Field Years

After Marshall Field died in 1906, John G. Shedd (1850-1926), of Shedd Aquarium fame, took over as president and led until he retired in 1922. The company, which went public in 1930, opened branches in the suburbs and built the Merchandise Mart to house the wholesale division. Once the core of the company, the wholesale division became a casualty of the Great Depression and had to be liquidated in 1936. The Merchandise Mart was sold to Joseph Kennedy (1888-1969) in 1945.

A post-war boom saw the company expand over the next 35 years by acquiring other stores around the country and opening branches throughout Illinois. Branches also opened outside the state in Houston in 1979 and Dallas in 1982.

Marshall Field & Company was purchased by BATUS in 1982 and the Target Corporation in 1990. In 2004, it was sold to the May Department Stores Company, and in 2006 was acquired by Macy’s. On September 9, 2006, all nine remaining branches of Marshall Field’s, including the flagship store on State Street, were renamed Macy’s, and the Field’s brand officially ceased to exist.

Atrium of the Marshall Field & Company Building in Chicago, Illinois
Atrium

 

Legacy of Marshall Field & Company

Marshall Field & Company revolutionized shopping in many ways, and set standards that are still in use today. First of all, Marshall Field’s was the first department store to have a European buying office, which was located in Manchester, England. The Walnut Room is the first tea room ever opened in a department store, and has been in operation since 1905.

The bridal registry and personal shopping both started at Field’s. In fact, personal shoppers were provided free of charge up until the very last day under the Marshall Field’s name. The store was the first to offer revolving credit, and was the first department store to install escalators. Finally, if you’ve ever been to a book signing, you can thank Marshall Field’s for the pioneering the concept.

 

From Field’s to Macy’s

The name change to Macy’s ruffled feathers in Chicago because it erased a piece of the city’s history. Macy’s was, however, required to keep certain features of the building, including the original nameplates from Marshall Field & Company. Thankfully, visitors and shoppers can still get a sense of the original splendor of Field’s, although it’s not quite the same.

Original Marshall Field & Company nameplate in Chicago
Original Marshall Field & Company nameplate

 

Great Clocks

Macy’s was also required to keep the Great Clocks that adorn the corners at both Washington and Randolph Streets. The first Great Clock was installed at the corner of State and Washington on the 1893 building on November 26, 1897. The second clock at State and Randolph went up in 1907. They weigh over seven tons and are my favorite features of the building.

The Great Clock of Marshall Field & Company in Chicago
The Great Clock

 

Holiday Traditions

During the holidays, the elaborate animated window displays outside the building became famous for their creativity and beauty. Visiting the windows became a Christmas tradition for many locals and visitors. I remember going “window shopping” on State Street as a kid, and these displays are still popular today.

Holiday window display at Macy's in Chicago, Illinois
Holiday window display at Macy’s
Holiday window display at Macy's in Chicago, Illinois
Holiday window display at Macy’s
Pinball-themed holiday window display at Macy's in Chicago, Illinois
Pinball-themed holiday window display at Macy’s

Another holiday tradition is to head up to the Walnut Room to see the 45-foot tall Christmas tree. It’s always beautifully decorated with about 1,200 ornaments and 6,000 lights.

Christmas tree in the Walnut Room at Macy's in Chicago, Illinois
Christmas tree in the Walnut Room

 

Reliance Building

On the southwest corner of Washington and State is the Reliance Building, which features plate glass windows and a terracotta tiled façade. It was built by businessman William Ellery Hale (1836-1898) with a unique construction process.

Reliance Building in Chicago
Reliance Building

Hale had purchased the lot, which contained the four-story First National Bank Building, in 1880. He wanted to demolish the building and construct a tower, but the tenants on the upper three floors refused to terminate their leases which didn’t expire until 1894. In 1890, Hale lifted the upper three floors on jack screws and demolished the ground floor. That same year, architect John Root (1850-1891) constructed a new ground floor and basement, and the first tenant, Carson Pirie Scott & Company, moved in. Unfortunately, Root died before he was able to complete the rest of his vision for the building and his plans have never been found.

When the leases expired and the tenants moved out, the upper floors were demolished and the rest of the building was completed by architect Charles Atwood (1849-1895). The Reliance Building opened in March 1895 and was the first skyscraper with electricity and telephone service in every office. It was originally used for retail and offices and fell into disrepair after the Great Depression. The building was renovated between 1994 and 1999 as a luxury hotel. It now houses the Staypineapple Hotel. It was designated a National Historic Landmark on January 7, 1976.

 

Carson Pirie Scott and Company Building (Sullivan Center)

At State and Madison is the old Carson Pirie Scott and Company Building, now the Sullivan Center. It was built in 1899 for retail firm Schlesinger & Mayer and designed by Louis Sullivan (1856-1924). H.G. Selfridge & Company purchased it in 1904, and a few weeks later sold it to Otto Young (1844-1906) who in turn leased it to Carson Pirie Scott and Company.

Carson Pirie Scott and Company Building in Chicago
Carson Pirie Scott and Company Building

The original flagship store of Carson Pirie Scott opened in the building in 1904 and closed in February 2007. The building is currently home to a branch of Target, which opened on July 26, 2012. Of particular interest is the marquee on the north face and the stunning ornamental iron entrance on the northwest corner designed by Sullivan. The building was designated a National Historic Landmark on May 15, 1975.

 

Harold Washington Library

Finally, a few blocks further south at State and Van Buren is the Harold Washington Library. It was built in 1991 and was named for Mayor Harold Washington (1922-1987). It was the largest public library building in the world when it opened. Of particular interest are the two-story central lobby and the Winter Garden on the 9th floor.

Harold Washington Library in Chicago
Harold Washington Library
Lobby of the Harold Washington Library in Chicago
Lobby
Winter Garden in the Harold Washington Library in Chicago
Winter Garden

 

Dearborn Street

We’ll continue our tour of by walking north along Dearborn Street, which is one of the important streets in the Chicago Loop. It runs north to south and contains some important government complexes as well as public art displays and historic late 19th century skyscrapers.

 

Monadnock Building

First, at Jackson and Dearborn is the Monadnock Building. It was built in two parts in two different years and by two different architectural firms – Burnham and Root in 1891 and Holabird and Roche in 1893. It makes up one of the four major buildings in the Printing House Row District along the 300 through 500 blocks of South Dearborn Street.

Monadnock Building in Chicago
Monadnock Building

The 16-story Monadnock Building, which was commissioned by Boston real estate developers Peter and Shepherd Brooks, is regarded as the tallest load-bearing brick building ever built. When it was completed, it was also the largest office building in the world with over 1,200 rooms. It was the first building in Chicago wired for electricity and one of the first to be fireproofed.

Entrance to the Monadnock Building in Chicago
Entrance

The Monadnock Building was modernized in 1938 and underwent a major restoration to its original condition starting in 1979. The dimly lit ground floor corridor is lined with shops and has an impressive cast aluminum staircase.

Hallway of the Monadnock Building along Dearborn Street in Chicago, Illinois
Hallway
Cast aluminum staircase of the Monadnock Building along Dearborn Street in Chicago, Illinois
Cast aluminum staircase

 

Federal Center

Across the street to the north is the Federal Center, which is comprised of the Kluczynski Federal Building, the Dirksen Federal Building, and the Loop Post Office. The complex, which surrounds Federal Plaza, was designed by Ludwig Mies van der Rohe (1886-1969) and built between 1960 and 1974. The design of the buildings is cold and sterile, which is fitting given their purpose.

Federal Plaza in Chicago
Federal Plaza

 

Flamingo

Gracing Federal Plaza is Flamingo by Alexander Calder (1898-1976). It was commissioned by the United States General Services Administration and unveiled on October 25, 1974. The sculpture weighs 50 tons and stands 53 feet high. The bright red color was chosen to offset the dull black and gray surroundings of the Federal Center buildings.

Flamingo by Alexander Calder at Federal Plaza in Chicago, Illinois
Flamingo by Alexander Calder

 

Marquette Building

The northwest corner of Adams and Dearborn is occupied by the Marquette Building, which was designed by Holabird and Roche. It was completed in 1895 and is one of the most impressive historic buildings in the Chicago Loop. It’s also tourist-friendly, making it easy to pop into the lobby to look around. The building was designated a National Historic Landmark on January 7, 1976.

Marquette Building in Chicago
Marquette Building

The entrance to the 16-story building features relief panels of the building’s namesake, Father Jacques Marquette (1637-1675), exploring the Chicago region in 1674.

Entrance to the Marquette Building in Chicago
Entrance

The lobby is incredibly beautiful, with a mosaic frieze depicting scenes of Father Marquette’s life and mission in Illinois. It was created by Louis Comfort Tiffany (1848-1933). Relief panels with the faces of Native American chiefs and French explorers associated with Marquette sit above each elevator. Just past the lobby is a small museum chronicling the history of the building.

Lobby of the Marquette Building in Chicago
Lobby
Mosaic panel in the lobby of the Marquette Building on Dearborn Street in Chicago, Illinois
Mosaic panel
Relief panel in the lobby of the Marquette Building on Dearborn Street in Chicago, Illinois
Relief panel
Museum in the Marquette Building
Museum

 

Four Seasons

A couple blocks away at 10 South Dearborn is Four Seasons by Marc Chagall (1887-1985). This large, colorful mosaic was donated to the city by the Prince Charitable Trust in 1974. It has four sides and is wrapped around a box 70 feet long, 14 feet high, and 10 feet wide.

Four Seasons by Marc Chagall in Chicago, Illinois
Four Seasons by Marc Chagall

Chagall created a model of the work in his studio in France. He then sent a mosaicist to install 128 separate panels, which feature thousands of pieces of glass and stone depicting six scenes of the city. Chagall arrived two weeks before the dedication and made adjustments based on his memory of Chicago 30 years earlier.

Four Seasons by Marc Chagall in Chicago, Illinois
Four Seasons
Four Seasons by Marc Chagall in Chicago, Illinois
Four Seasons
Marc Chagall's signature on Four Seasons by Marc Chagall in Chicago, Illinois
Marc Chagall’s signature

 

Daley Plaza

Further north at Washington Street is Daley Plaza, which frequently hosts civic events, farmers’ markets, and festivals. Christkindlmarket, the traditional German Christmas market every holiday season, is the most popular.

Daley Plaza in Chicago, Illinois
Daley Plaza
Daley Plaza
Daley Plaza
Farmer's Market at Daley Plaza in Chicago, Illinois
Farmer’s Market at Daley Plaza

 

The Picasso

Daley Plaza features one of the city’s best known pieces of public art. The untitled Picasso sculpture, which everyone refers to as “The Picasso”, was designed by Pablo Picasso (1881-1973) and commissioned by the architects of the Daley Center. It was made to specification at US Steel in Gary, Indiana, and erected in 1967. When the City of Chicago tried to pay Picasso for the work, he refused and said it was a gift. Initially, the sculpture was met with criticism and controversy, but it has grown into one of the city’s most important symbols. The legendary artist never saw the finished product in person.

The Picasso at Daley Plaza in Chicago, Illinois
The Picasso

 

Daley Center

The Richard J. Daley Center is a 30-story building on the north side of Daley Plaza. It was originally named Chicago Civic Center and was renamed for Mayor Richard J. Daley (1902-1976) a week after his death. When it was completed in 1965, it was the tallest building in Chicago. It houses offices and courthouses for Cook County as well as offices for the City of Chicago.

Daley Center along Dearborn Street in Chicago, Illinois
Daley Center

 

Miró’s Chicago

Across the street south of Daley Plaza is Miró’s Chicago. In 1979, Joan Miró (1893-1983) was commissioned to create a sculpture for the city. It was erected 2 years later in 1981, standing 40 feet high and made of concrete, different metals, and tile. The sculpture was originally titled The Sun, the Moon, and One Star. It sits next to the Chicago Temple, a mixed-use church building that was once the tallest in the city.

Miró's Chicago in Chicago, Illinois
Miró’s Chicago

 

Goodman Theatre

Finally, on Dearborn between Randolph and Lake is the Goodman Theatre. Founded in 1925, it’s Chicago’s oldest active nonprofit theatre organization. It’s named for Kenneth Sawyer Goodman, a local playwright who died in 1918 during the Spanish flu pandemic. The original theatre was located at the Art Institute of Chicago and moved to its current location in 2000. The building was designed by KPMB Architects.

Goodman Theatre in Chicago
Goodman Theatre

 

LaSalle Street

Continuing our tour of the Chicago Loop, we’ll head west to walk south down LaSalle Street. It’s named for French explorer Robert de La Salle (1643-1687) and is the home of the city’s financial district.

 

Thompson Center

The James R. Thompson Center takes up the entire block bordered by LaSalle, Lake, Clark, and Randolph. It’s an interesting futuristic-looking glass building designed by architect Helmut Jahn (1940-2021). It opened in May 1985 as the State of Illinois Center and was renamed for James R. Thompson (1936-2020) in 1993, who served as governor from 1977 to 1991. The building permanently closed in 2022 and will be renovated to house offices for Google (as of February 2024).

James R. Thompson Center in Chicago
James R. Thompson Center

The Thompson Center housed offices of the State of Illinois and served as a secondary state capitol. It’s 17 stories high and visitors can see all of the floors from the skylit atrium.

Atrium of the James R. Thompson Center in Chicago
Atrium

 

Monument with Standing Beast

Monument with Standing Beast is a 10-ton sculpture located in front of the Thompson Center. It was erected in 1984 by Jean Dubuffet (1901-1985). It’s made of fiberglass and looks like large distorted pieces of a puzzle. Some people call it “Snoopy in a Blender”.

Monument with Standing Beast by Jean Dubuffet in Chicago, Illinois
Monument with Standing Beast by Jean Dubuffet
Monument with Standing Beast by Jean Dubuffet in Chicago, Illinois
Monument with Standing Beast by Jean Dubuffet

 

Cadillac Palace Theatre

On the opposite corner at LaSalle and Randolph is the Palace Theatre, which opened in 1926 as the New Palace Theatre. It was designed by Rapp and Rapp, who took inspiration from Fontainebleau and the Palace of Versailles. The theatre was turned into a rock venue and renamed the Bismarck Theatre in 1984. It was renovated and renamed the Cadillac Palace Theatre in 1999. The theatre has a capacity of 2,344 and is a venue for Broadway plays and musicals.

Palace Theatre in Chicago
Palace Theatre

 

Chicago City Hall

Chicago City Hall takes up an entire block bounded by LaSalle, Randolph, Washington, and Clark. The center of city government has sat on that spot from 1853 to 1871 and from 1885 to the present. It houses the offices of the mayor, city clerk, and city treasurer, as well as a handful of city departments and aldermen’s offices. The chambers of the Chicago City Council sit on the west side of the building while the east side contains offices for Cook County.

Chicago City Hall on LaSalle Street in Chicago, Illinois
Chicago City Hall

The current Chicago City Hall was built on the site of the old city hall and courthouse, which was built in 1853 and burned down during the Great Chicago Fire of 1871. Abraham Lincoln’s body laid in state there during his funeral in 1865. That building was replaced by another city hall and courthouse built in the French Empire style, standing from 1885 to 1905.

Chicago City Hall seen from Daley Plaza
Chicago City Hall seen from Daley Plaza

The current building was designed by Holabird and Roche in the Classical Revival style and constructed between 1905 and 1911. It stands 11 stories high and features a 38,800 square foot green roof installed in 2001.

 

Rookery Building

Three blocks south at Adams Street is the Rookery Building, which was built between 1886 and 1888. It was designed by Burnham and Root and is considered one of their masterpieces. Upon completion, the 12-story building was one of the tallest in the world at the time. The building was designated a National Historic Landmark on May 15, 1975.

Rookery Building in Chicago
Rookery Building
Rookery Building
Rookery Building

The Light Court on the ground floor center of the building was designed by Frank Lloyd Wright (1867-1959) in 1905. Wright had his offices in the Rookery Building in 1898.

Light Court of the Rookery Building
Light Court
Light Court of the Rookery Building
Light Court

 

Federal Reserve Bank of Chicago

At LaSalle and Jackson is the Federal Reserve Bank of Chicago. It’s one of 12 regional Federal Reserve Banks, serving the Seventh Federal Reserve District. The building was completed in 1922 and is 17 stories high. It had one of the largest vaults ever constructed at the time.

Federal Reserve Bank of Chicago in Chicago, Illinois
Federal Reserve Bank of Chicago

 

Money Museum

The Federal Reserve Bank of Chicago houses the Money Museum, which opened in 2001. It’s free and open year-round from 10am to 5pm, Monday through Friday except bank holidays (as of February 2024). Visitors over 18 must provide a valid photo ID, and everyone must go through a security screening.

Money Museum at the Federal Reserve Bank of Chicago in Chicago, Illinois
Money Museum

The Money Museum contains displays on the history of money in the United States, the fight against counterfeiting, and much more. A bag of shredded money is given to visitors as a small souvenir. It takes about 45 minutes to go through on a self-guided tour.

$10,000 bill at the Money Museum at the Federal Reserve Bank of Chicago in Chicago, Illinois
$10,000 bill

 

Chicago Board of Trade Building

At the south end of LaSalle Street is the Chicago Board of Trade Building, which opened on June 9, 1930 for the Chicago Board of Trade (CBOT). The CBOT, which was founded on April 3, 1848, has been at the location since 1885. The Art Deco structure was designed by Holabird and Root and was the tallest building in Chicago until 1965. At 19,000 square feet, it once had the world’s largest trading floor. The once-bustling trading floor was open to visitors in the past but it’s now a quiet office space. I remember taking a field trip there during elementary school and feel fortunate to have seen it in action.

Chicago Board of Trade Building in Chicago, Illinois
Chicago Board of Trade Building

The Chicago Board of Trade Building is crowned by an aluminum statue of Ceres, the Roman goddess of agriculture. It’s 31 feet tall and weighs 6,500 pounds. It was designed by John Storrs (1885-1956) and was assembled from 40 pieces. The building was designated a National Historic Landmark on June 2, 1978.

Ceres on the Chicago Board of Trade Building in Chicago, Illinois
Ceres

The clock on the LaSalle Street façade is 13 feet in diameter and is flanked by the hooded figures of a Babylonian holding grain and a Native American holding corn. In popular culture, the building was the headquarters of Wayne Enterprises in the 2005 blockbuster Batman Begins, and was used in the infamous funeral scene in the sequel, The Dark Knight, in 2008.

Clock on the Chicago Board of Trade Building in Chicago, Illinois
Clock

 

Willis Tower

Next, we’ll walk two blocks west down Jackson to the Willis Tower. It’s the tallest building in Chicago and once the tallest in the world. The building is still called by many Chicagoans (including myself) by its original name, the Sears Tower. (Note: if you follow the strict local definition of the area’s boundaries, the Willis Tower is NOT technically in the Chicago Loop.)

Willis Tower (Sears Tower) in Chicago
Willis Tower

 

History of the Willis Tower

The Sears Tower was built in the early 1970s for Sears, Roebuck and Company, then the largest retailer in the world. Construction started in 1970 and it was completed in 1973. The building was designed by Fazlur Rahman Khan (1929-1982) and Bruce Graham (1925-2010).

Willis Tower
Willis Tower

The Sears Tower was constructed in phases of nine “bundled tubes“, which were essentially separate buildings. It was the first building to use this architectural innovation. For 25 years it was the tallest building in the world at 108 stories and 1,450 feet high.

Willis Tower
Willis Tower

The building was the headquarters of Sears from 1974 to 1995, but although they had vacated the building, they held the naming rights until 2003. After the naming rights expired, the building was still referred to as the Sears Tower for another six years. Willis Group acquired the naming rights in March 2009, and the name officially changed to the Willis Tower on July 16 of that year. The name has yet to stick.

 

Skydeck

The observation deck on the 103rd floor, the Skydeck, opened on June 22, 1974. It’s the highest observation deck in the United States and one of the top tourist attractions in Chicago. Timed admission starts at US$32 for anyone age 12 and up and US$24 for children age 3 to 11 (as of July 2023). There are other admission packages including expedited entry.

Skydeck at Willis Tower (Sears Tower) in Chicago
Skydeck

Elevators reach the Skydeck in 60 seconds. At the top are interpretive panels with several facts about the building. On a clear day, it’s possible to see Illinois, Indiana, Wisconsin, and Michigan. You can also see other buildings in the Chicago Loop and beyond. No matter what time of day you visit, the views are breathtaking.

Skydeck at Willis Tower (Sears Tower) in Chicago
Skydeck

One of the highlights of the Skydeck is the Ledge, which is a series of glass boxes visitors can climb onto and look straight down to ground level. These boxes were installed in 2009 and opened to the public on July 2 of that year. Each one can accommodate five tons. It’s an exhilarating yet terrifying experience.

The Ledge on the Willis Tower Skydeck
The Ledge
The Ledge on the Willis Tower Skydeck in Chicago, Illinois
The Ledge
Me sitting on the Ledge at the Skydeck at Willis Tower (Sears Tower) in Chicago
Me sitting on the Ledge

 

Printer’s Row

The final part of the walking tour of the Chicago Loop takes us to Printer’s Row. It’s a neighborhood that was once full of printing and publishing companies. The majority of the buildings have now been converted into lofts. Most of the interesting buildings lie along Dearborn Street. Among them are the Pontiac Building, the New Franklin Building, and the M.A. Donohue Building. (Note: this is another area of Chicago not considered by locals to be in the Loop proper.)

Dearborn Street in Printer's Row in Chicago
Dearborn Street in Printer’s Row

 

Pontiac Building

The Pontiac Building was built in 1891 by Holabird and Roche. It’s the oldest surviving building in downtown Chicago built by the firm. It stands 14 stories high and was built with a steel frame covered in brick. The building features terra cotta soffits and limestone piers with decorative capitals.

Pontiac Building in Printer's Row Chicago
Pontiac Building

 

Franklin Building

The Franklin Building was built in 1916 for the Franklin Printing Company. It was designed by George C. Nimmons (1865-1947) in 1912. It housed printing presses until 1983, and was converted to residential units in 1989. The terra cotta tiles are the main design feature.

Franklin Building in Printer's Row Chicago
Franklin Building

 

M. A. Donohue Building

The M. A. Donohue Building was occupied by publisher M. A. Donohue and Co. It was designed in the Romanesque style by Julius B. Speyer (1845-1916) and built in 1883. An annex was added in 1913. The company published children’s books in the building until the 1960s. In 1979, the M. A. Donohue Building became the first factory building in Chicago to be converted to residential lofts.

M. A. Donohue Building in Printer's Row Chicago
M. A. Donohue Building

 

Dearborn Station

And the south end of Dearborn Street is Dearborn Station. This former railway station built in 1885 was in use until May 1, 1971. The architect was by Cyrus L. W. Eidlitz (1853-1921), who designed it in the Romanesque Revival style. The most striking feature is the 12-story clock tower. Dearborn Station once served 17,000 passengers a day but has been a quiet office building since the 1980s.

Dearborn Station in Printer's Row Chicago
Dearborn Station
Ornamental stonework on Dearborn Station in Printer's Row Chicago
Ornamental stonework
Dearborn Station in Printer's Row Chicago
Dearborn Station

 

Where to Eat in the Chicago Loop

The Loop has some of the best food for those on the go in Chicago. I’ve been to lots of restaurants in the area, but this post will only cover the one that I’ve been to since 2015. I’ll add more as I visit them.

 

Gayle V’s Best Ever Grilled Cheese

If you’re looking for comfort food, head to Gayle V’s Best Ever Grilled Cheese. It’s located underground on the Pedway at State Street. All the ingredients are local and farm-fresh.

Gayle V's Best Ever Grilled Cheese in the Loop, Chicago, Illinois
Gayle V’s Best Ever Grilled Cheese
Gayle V's Best Ever Grilled Cheese in the Loop, Chicago, Illinois
Gayle V’s Best Ever Grilled Cheese

I’m not convinced it’s the best ever, but they definitely make a great grilled cheese. I had a combo with a tomato soup and it filled me up nicely on a cold winter day. Service was a little slower than we expected but it turned out to be worth the wait.

Grilled cheese and tomato soup at Gayle V's Best Ever Grilled Cheese in the Loop, Chicago, Illinois
Grilled cheese and tomato soup

 

Map of the Chicago Loop

Author

Owner of Paisadventure. World traveler. Chicago sports lover. Living in Colombia.

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