Located on the shores of Lake Michigan, Chicago is one of the most beautiful cities of America. The Chicago River runs through the heart of the city. Photo courtesy of City of Chicago Photo /Choose Chicago.


The Windy City has the dramatic skyline, architectural marvels, dynamic entertainment, and colorful history. Join noted gastroenterologist Dr. Jun Ruiz as he rounds ups Chicago’s iconic attractions from his multiple visits.

Chicago is the third most populous city in the United States, one of the most ethnically diverse cities, and the biggest urban center in Midwestern America (also known as Midwest). It is also considered as one of the most beautiful metropolises in America. Located on the shores of Lake Michigan, Chicago experiences strong gusts of wind, giving it the nickname “Windy City.” Another popular nickname for Chicago is “Second City”, signifying Chicago’s rebirth after the great fire devastated the city in 1871.

International tourists are more inclined to visit the highly urbanized coastal American cities, like New York, Miami, Los Angeles, and San Francisco, due to the influence of popular culture and the proximity from Europe and Asia. However, including domestic tourists traveling within the United States, Chicago has 54 million visitors annually, second only to New York City. Chicago has set the stage for blockbuster movies and popular television programs like Home Alone, Ferris Bueller’s Day Off, Batman Begins, and E.R.

Taking a cruise along the Chicago River is one of the best ways of sightseeing in the city. Photo courtesy of City of Chicago Photo /Choose Chicago.

Chicago is renowned worldwide for its unique and innovative architecture of the skyscrapers, outstanding art scene, cultural institutions, diverse gourmet cuisine, and extensive shopping opportunities. Chicago offers a lot of things for tourists to enjoy, making their visit to the “Heart of America” a truly memorable one.

The first time I visited Chicago was in the 1990s, when I was applying for a medical residency in the United States. The last time I stopped by was last year after my American medical recertifying exam, when I made a quick visit to meet up with very good friends. All in all, I have had five trips to Chicago and most of the time was spent for catch-up and social occasions. Thus, my roundup of Chicago’s most popular attractions took two decades, and was not achieved in one single trip.

The author Dr. Jun Ruiz enjoys the outdoors by the Pritzker Pavilion. This photo was taken in 2013. Photo courtesy of Dr. Matthew Libiran.

The Dulanas family graciously accommodated me during my first two trips to Chicago, especially I have a close relationship with my Aunt Virginia. My very good friends Leni and Bong Kitane, and Matthew and Gretchen Libiran alternately hosted me in my later visits. I also have a few other friends from Chicago who are also from my hometown that I keep in touch.

The Magnificent Mile

Whether you are a serious shopper or not, the Magnificent Mile is a good introduction to Chicago. This is an upscale area of North Michigan Avenue, the 13-block section running from Oak Street in the north side up to the Chicago River. It is the city’s premier shopping district, lined with mid-range and high-end retail stores, shopping malls, restaurants, and posh hotels. Shopaholics will find pleasure in the three vertical malls (like the Macy’s Water Tower Place), department stores, luxurious boutiques, and specialty stores, like Crate and Barrel, Nike Town, Gap, and Apple Store. I was already contented with window-shopping. This fashionable and beautiful boulevard reminds me of Fifth Avenue in Manhattan, with its skyscrapers, wide sidewalks, plush stores, and a sea of people.

The Great Chicago Fire of 1871 burned for 36 hours from October 8 to 10, destroying most of the buildings in downtown, all of which were made of wood. This defining event in Chicago’s history resulted in 300 deaths, and around 100,000 persons were left homeless, the latter number constituting one-third of the population.

In the aftermath, the Chicago Water Tower was among the only few left standing. It was originally commissioned to house a standpipe that stabilized the main water pressure. It is a castellated Gothic Revival-style limestone building that is now a monument to that event. The 154-feet tower was built only two years earlier before the fire. This beloved landmark currently houses the City Gallery, café, theater and a visitors’ center.

The city of skyscrapers and architectural innovations

After two decades, Chicago rose from the ashes, and architectural geniuses rebuilt the city with pioneering skyscrapers, like the Marquette Building, the Rookery, and the Monadnock Building. In the 20th century, Chicago earned a great reputation as a center of architectural innovation, where new building techniques were developed and original creative expression reflected the history of American architecture. Today, Chicago’s downtown skyline is dominated by a diverse heritage of skyscrapers, both modern and historic. The more residential architectural styles, like Queen Anne, are found in the suburbs of the city.

Chicago Water Tower survived the Chicago Fire of 1871. It is a castellated Gothic style limestone building. Photo courtesy of Pixabay

For those interested in architecture along Michigan Avenue, these following buildings are must-sees. The 100-story International-styled 875 North Michigan Avenue Building (John Hancock Center) stands out in the Chicago skyline in its dark metallic looking exterior. The major attraction is the 360 Chicago Observatory, located on the 94th floor, where you can admire panoramic views over Chicago. At the southern end of the Magnificent Mile stand two spectacular historical buildings. The Tribune Tower is the 36-story neo-Gothic designed limestone building and home of the newspaper Chicago Tribune. Wrigley Building is one of Chicago’s most beloved buildings, and this Gothic-style white terra-cotta landmark boasts two towers connected by arcades, a massive cupola, and a giant four-sided clock. When illuminated, the landmark dazzles at night.

The Chicago River runs through the heart of the city, parallel to the lakeshore, and is crossed by 32 bridges. It was a major commercial waterway as part of the Illinois and Michigan canals around two centuries ago. Now, the riverfront is a fashionable place to hang out with its restaurants, condominiums, and marinas. Starting spring time, you will see sailboats, sightseeing and tour boats.

Taking a cruise down the Chicago River is definitely one of the best ways for city sightseeing. In 2013, I joined my friends Matthew and Gretchen in the guided 75-minute Chicago Architectural River Cruise. We enjoyed our time from this vantage point, as it was very educational and inspiring to admire the spectacular architectural highlights. Even if you’re only visiting for a day or two, put this activity on your list. Among the additional architectural landmarks I was impressed were: the two circular towers of Marina City, which look like giant corncobs as a symbolic tribute to the farming industry; the reflective, green-tinted curved edifice of the Post-Modern 333 West Wacker Drive Building; and the glamorous Trump International Tower, the second tallest building in Chicago.

Willis Tower

The tallest building in Chicago is the glass-and-steel 110-story Willis Tower that stands at 1,454 ft. It was built in 1973 to be the Sears National Headquarters, and was the world’s tallest structure at that time. When I first visited the observatory called Skydeck on the 103rd floor during my first visit, it was still called Sears Tower. In 2009, it was renamed Willis Tower. In 2010, Burj Khalifa in Dubai opened as the new world’s highest building.

The tallest building and the top paid tourist attraction in Chicago is the Willis Tower. Photo courtesy of Pixabay/272447.

The Willis Tower is Chicago’s number one paid tourist attraction. Take a quick ascent to the clouds, as the elevator ride to the glass-enclosed deck takes only 70 seconds. Overlooking Lake Michigan on the east side, the panoramic views are stunning. On my second time, I experienced the Ledge – the newly added glass-floored platform that extends out of the deck where you can look directly down at the city view with some fear factor.

Millennium Park

Located close to many of the major attractions and bordered by Michigan Avenue in downtown Chicago is the Millennium Park. It is an architectural and art-filled jewel that opened in 2004 to celebrate the 21st century. It provides recreation and entertainment all year round, either free summer concerts, or an ice-skating rink during winter. This is my favorite place in all of Chicago, and I made sure I spent leisure time here in my last three visits.

The centerpiece is the iconic elliptical-shaped sculpture officially called Cloud Gate, and nicknamed “The Bean”. The huge sculpture is a masterpiece by renowned British sculptor Anish Kapoor. It has a highly polished, mirror-like stainless steel surface inspired by liquid mercury, as seen as visual effects in science-fiction movies.

The Cloud Gate has quickly become Chicago’s most iconic sight. It anchors the downtown park, and its shiny exterior of this 110-ton sculpture reflects the park, the surrounding skyline, and the excited tourists. Do not forget to take a fun selfie by the Bean, despite it being ubiquitous on social media platforms like Facebook and Instagram.

Another showpiece is the soaring beauty of the outdoor Jay Pritzker Pavilion.  It is the venue of several summer music festivals and concerts. The unique design features a “billowing stainless steel headdress with petals” reaching out into the sky that frames the concert stage. The pavilion and lawn beneath this lovely canopy can accommodate up to 14,000 people. Another top attraction is the Crown Fountain, which is composed of two fascinating 50-ft glass blocks that project video images of Chicago locals, whose mouths open to sprout water down below.

Navy Pier

Navy Pier is the newest “old jewel” in Chicago’s crown and iconic part of the Chicago skyline. Stretching into Lake Michigan, it originally opened in 1916 as a municipal wharf and a shipping facility. In World War II, the US Navy took over and used it as a naval training facility; hence, the name. In 1995, it opened in its present incarnation as a modern amusement and cultural park, becoming one of Chicago’s most popular tourist attractions. Navy Pier comes to life in the summer, with live music, special events and fireworks display. The attractions, lakefront views and the cool breeze kept me busy one whole morning during my last trip.

Navy Pier is a recreational center, where there are shops, restaurants, theater, and a Ferris wheel. Photo courtesy of City of Chicago/Choose Chicago.

Today, Navy Pier is a recreational center, where you can enjoy gardens, shops, restaurants, concerts venues, and theater. Adding fanfare to the park, there is a 150-ft Ferris wheel and an old-fashion carousel at Navy Pier.  The Ferris wheel offers fine views of the lake during the day, and is illuminated at night, visible from anywhere on the Lake Shore Drive. Other entertainment activities include a 3D Imax Theater, the Chicago Shakespeare Theater, the Crystal Gardens, an ice skating rink, and the Chicago Children’s Museum. Several boat cruises leave from here on various sightseeing excursions.

There is more to see in Chicago than what I can write in this travelogue. The art museums are world-class, the Art Institute of Chicago being the most famous. There are other green parks, the most celebrated is Grant Park. Here you can find the beautiful Buckingham Fountain and the Museum Campus at the lakefront, home to the Field Museum, the Adler Planetarium, and Shedd Aquarium. Chicago is a sports town where the passion is deep among fans.  You can watch the Cubs at Wrigley Field, or watch basketball at the United Center, the house that Chicago Bulls superstar Michael Jordan built.

The author Dr. Jun Ruiz finds relaxing time at Navy Pier. This picture was taken in 2019. Photo courtesy of Leni Ligunas-Kitane.

Chicago has always been a favorite destination of mine, not just for being the home of my wonderful friends whom I enjoy visiting, but also for the plethora of attractions that make every trip exciting and memorable. From the visual delights of the soaring skyscrapers, to the endless fun in Navy Pier and the Millennium Park, and to the multitude of fine museums, Chicago has always something for everyone’s interest. There are more hidden gems in Chicago that travelers like me need to explore, see and experience. When the COVID-19 health crisis ends and it is safe to travel again, another visit to Chicago is very likely.

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