These are some of our favorite Chicago attractions. There’s so much to do in the Windy City that these are only a few of what Chicago has to offer. We recommend several visits!
And check out my history of Illinois and Chicago for some more fun facts and insight.
We hope this helps inform your next Chicago trip!
Grant Park
Grant Park is a 319-acre park, which has been providing an enjoyable respite for Chicagoans since 1844. It was officially named Grant Park after Ulysses S. Grant in 1901. Most people do not know that Lake Michigan’s shoreline, in the 1800’s, came to the edge of Michigan Avenue. Fort Dearborn was constructed at the shoreline on Michigan Avenue. After the Great Chicago Fire, much of the debris was used as a landfill which eventually pushed the shoreline back to its current location, east of Lake Shore Drive. This essentially created the park area.
The park wouldn’t be a park without the direct involvement of Montgomery Ward, the scion of the retail stores that bore his name. Many of the civic leaders at the time wanted to use the park area for the construction of more buildings for businesses. Montgomery Ward fought to keep the land public and free of buildings. Many court battles ensued, but Ward eventually succeeded in keeping the large area public.
Today, the park is a combination of parks within the park. These include Millennium Park and Maggie Daley Park. The Art Institute of Chicago is on its western edge. Buckingham Fountain is somewhat in the middle. The Adler Planetarium, Field Museum of Natural History, and Shedd Aquarium are on the edge. The Petrillo Music Shell Today (formerly the Grant Park Bandshell) showcases classical music and jazz concerts.
Grant Park is beautiful and has so much to offer. Chicagoans should be grateful to Montgomery Ward for preserving this area for all. As a tourist, Grant Park is a must-see location. We enjoyed the Chicago Segway tour, a simple and fun way to traverse the width of the park.
Clarence F. Buckingham Memorial Fountain
The Clarence F. Buckingham Memorial Fountain has nothing to do with Buckingham Palace, although the Queen of England did see the fountain when she visited Chicago. In 1959, Queen Elizabeth II visited Chicago to commemorate the opening of the St. Lawrence Seaway. She came on the royal yacht, Britannia, and reportedly saw the fountain first when she arrived.
The Buckingham Fountain was inspired by a fountain in Versailles, outside of Paris. It is much larger than its French counterpart and circulates more than three times the water. The basin of the fountain symbolizes Lake Michigan.
It’s a beautiful fountain and operates between April and October. It does get cold in Chicago, so operating a fountain during the winter doesn’t make a lot of sense. If you visit Millennium Park, it’s worth the walk into Grant Park to visit Buckingham Fountain.
Millennium Park
Millennium Park is a park part of Grant Park and is a major tourist draw to Chicago. It is located on top of the original Illinois Central railroad lines in Grant Park. The park opened in 2004 but the idea began after Mayor Richard M. Daley took office in 1989. The name of the park was meant to draw attention to Chicago in the 21st century and was meant to open sooner than 2004. There were many problems to overcome, not the least of which was the legislation that Montgomery Ward (retailer of the same name) instituted to ensure that Grant Park was only for the public. The city wanted a concert venue, and this would be a business in the park, which would be in violation of Ward’s legislation. Frank Gehry proposed that the concert venue would be a work of art, and funding came from the Pritzker family who owns the famed Hyatt Hotels chain.
Probably the most memorable icon of this park is the Bean, officially known as Cloud Gate. It’s probably the most photographed spot in the park.
We definitely recommend you visit Millennium Park. It is Grant Park reimagined for the next millennium. In the spring and summer, there are plenty of food vendors nearby and there are numerous sculptures to observe and photograph. From Millennium Park, you can play mini golf, stroll to Maggie Daley Park or move farther south to one of the three major museums.
There is plenty to do and see. We love Grant Park, and Millennium Park is a great addition to a fine investment in public land for the city.
The Field Museum of Natural History
The Field Museum of Natural History is named for Marshall Field, the great department store businessman, who donated $1 million. It opened in 1894 displaying items from the World’s Columbian Exposition of 1893. The original location of the museum is where the Museum of Science and Industry is now located on the South Side. Its current location opened in 1921.
The Field Museum has more than 40 million specimens and artifacts in natural history and attracts millions of visitors every year. Marshall Field was initially reluctant to give any money to fund the museum. He was ultimately convinced to contribute $1 million as a means of preserving his legacy. The year after his death, his will specified another $8 million donation.
It’s a splendid museum to photograph, even if you didn’t go in. The architecture was inspired by the Greeks, particularly the Temple of Minerva in Athens.
The Field Museum is probably most known for Sue, a 90-percent complete large tyrannosaurus dinosaur skeleton. She’s named after the museum’s paleontologist Sue Hendrickson, who discovered the dinosaur in 1990 during an exploratory trip north of Faith, South Dakota. If it wasn’t for a flat tire, Sue might not have been discovered. It took 17 days to extract the bones.
Sue is still there, but now an even larger dinosaur takes center stage. Máximo is a titanosaur skeleton cast of the largest dinosaur ever unearthed. The two-story tall dinosaur was discovered in Argentina in 2014 and weighed 70-tons when alive.
You can easily spend more than a day in this museum; there is so much to see. It is one of the largest natural history museums in the world and should be on your list when you visit Chicago.
Madeline and I visited the museum when we were in high school and were very impressed with Sue. I can’t imagine looking at Máximo these days. You’ll also notice a T-rex sculpture outside the museum. If you’re in Grant Park, you can easily see it. When we were in high school, Madeline didn’t seem terribly interested in the Field Museum—it had a bunch of old things. Now she’s fascinated with history, relics, fossils and the like. Neither of us were interested in history in high school. It was a memory contest of names, places and dates. Boring! Now history is taught with context and relevance. How times have changed.
The Adler Planetarium
The Adler Planetarium opened in 1930 and was the first planetarium in the United States. The planetarium is named after Max Adler, who was an executive with Sears in Chicago. Max donated $500,000 in 1928 to construct the planetarium. It was originally planned to part of the Museum of Science and Industry, which was led by Max’s brother in law, Julius Rosenwald. There were substantial delays in the renovations of Science and Industry forcing Max to look for another location and deciding on its current location.
The museum is in an excellent location and is frequently used for taking pictures of the Chicago skyline. The museum attracts over 500,000 visitors annually.
Madeline and I visited the museum when we were in high school and were fascinated by the show, which depicted the heavens, stars, planets, suns, etc. It was a grown-up presentation at the time, but now there are plenty of programs for children and adults.
The Shedd Aquarium
The Shedd Aquarium opened in 1930 and was the first inland aquarium with a permanent saltwater fish exhibit. To achieve this, a train car was sent to Florida to harvest the saltwater from the sea and it returned to Chicago by rail. At the time it opened, it was the largest aquarium in the world. Today, it’s ranked seventh.
Visitors to Chicago prefer the Field Museum and the Shedd Aquarium over the Adler Planetarium. Both the Field and Shedd attract more than 1 million people annually, compared to the approximately half million visitors who go for the planetarium. The aquarium is regularly in the top five most visited aquariums in the United States.
Since Madeline and I visited the aquarium in high school, it’s grown significantly and is certainly worth your time to visit. Since the Shedd Aquarium is so close to the Field Museum, Adler Planetarium and Grant Park, it should definitely be on your list of places to visit.
The Art Institute of Chicago
Founded in 1866, the Art Institute of Chicago was opened as a school for artists. Its first building opened in 1870. Built mostly of wood, it succumbed to the Great Chicago Fire a year later. The current building originally was built for the World’s Columbian Exposition of 1893.
As you face the building from Michigan Avenue, the iconic bronze lions that flank the stairway look down at you. These were a gift from Helen Field, the wife of Marshall Field, the department store magnate.
Madeline and I have regularly visited the Art Institute over the years. It would take several days to see all of it. We are drawn to the impressionist paintings and the spectacular A Sunday on La Grande Jatte — 1884, the most significant work by Frenchman Georges Seurat. It demonstrates the pointillism technique, which creates a scene using thousands of tiny dots of paint. The work is quite large at 82 inches tall and 121 inches wide. We loved this piece so much we bought a small reproduction that we proudly display in our home.
There are plenty of masterpieces to view by Georgia O’Keeffe, Vincent van Gogh, Claude Monet, Édouard Manet, Some of its most famous are Grant Wood’s American Gothic, Marc Chagall’s America Windows and Edward Hopper’s Nighthawks. The Thorne Miniature Rooms feature highly detailed miniature dollhouses with furniture and lighting. Of course, there are many other famous artists including Pablo Picasso, Salvador Dalí, René Magritte and more.
We love this museum. Back in the old days, it used to be free every day. Now, there are certain free days but plan your schedule ahead of time. Or you can give a tax-free donation to the institute. The Art institute is not to be missed during your next Chicago visit.
The Magnificent Mile
Michigan Avenue is more than 12 miles in length, but most tourists spend their time on the Magnificent Mile section, known for high-end shopping like Water Tower Place. These days, there are medium and lower priced stores intermingled on this stretch of North Michigan Avenue. The Magnificent Mile is a nice place to find some historic architecture of Chicago, including the Tribune Tower, the Chicago Water Tower, the Wrigley Building, the old Playboy Tower.
Madeline and I remember both our mothers wearing their mink stoles when they walked down the Magnificent Mile. It was a place to be seen while you were sightseeing.
We walked up the Mile, beginning at the Chicago River and going to the point where it begins to merge with North Lake Shore Drive. We then turned around and headed back on the other side of the street to see more things. There is always something interesting to see on Michigan Avenue.
The Signature Lounge at the 96th
When we were dating in high school, I couldn’t afford to take Madeline to the Ninety-fifth Restaurant, the restaurant on the 95th floor of the John Hancock Center. Now it’s called the Signature Room at the 95th, and the building is called 875 North Michigan Avenue (but will still call it the Hancock).
I could, however, afford a pop on the 96th floor, which was a bar. They let high school students nurse a Coke and maybe order some peanuts or chips. The views from this bar were spectacular.
Today, it’s called the Signature Lounge at the 96th. A cocktail or beer there might seem expensive, but when you add the view, it’s a great deal. You need to visit the Signature Lounge if you want an amazing great view of Chicago and Lake Michigan.
The Hancock does have an observation deck on the 94th floor, called 360 Chicago. But the ambiance of the Signature Lounge is well worth the price of a drink. We go back regularly as the picture will attest. We’re smooching to mark the occasion, with Chicago spreading out behind us. What could be more romantic?
The Willis Tower (formerly The Sears Tower) is taller than the Hancock and has an observation deck, too. However, the Hancock is still my choice when we come back.
Old Chicagoans still call them Sears Tower and the Hancock. We also call the ballpark where the White Sox play Comiskey Park, not U.S. Cellular Field or Guaranteed Rate Field. We understand naming rights, but some things aren’t supposed to change. Try asking for ketchup on a Chicago hot dog sometime, you’ll understand.
Chicago Water Tower
The Chicago Water Tower is another iconic structure on the Magnificent Mile, which is North Michigan Avenue. Built in 1869, the tower drew the city’s water from Lake Michigan. It was one of the few structures still standing after the Great Chicago Fire. It’s the second-oldest water tower in the United States.
Don’t confuse this building with its better-known neighbor, Water Tower Place. The latter is a mecca for shopping and draws many tourists in search of the perfect gift. We would “window shop” in Water Tower Place because it was conveniently located close to the John Hancock Center (now 875 North Michigan Avenue) where we’d go for drinks.
Tribune Tower
The Tribune Tower is one of the most famous buildings in Chicago. If you are even moderately interested in architecture, this is a great photo opportunity. It originally was built in 1868 but succumbed to the Great Chicago Fire in 1871. It was rebuilt in 1925 and was home to the Tribune Company, which included the famous newspaper and later WGN radio and TV stations.
Although it was an office building for many years, it is now in the process of conversion into condominiums expected to finish in 2020. We never tired of looking at it, particularly on a sunny day when the sun hits it or at night when it’s all lit up.
Wrigley Building
Built in 1924, the Wrigley Building was headquarters to the famous chewing gum company. It anchors the south end of the Magnificent Mile of North Michigan Avenue. The Wrigley Building was Chicago’s first air-conditioned office building and was the first major office building to be constructed north of the Chicago River.
Architectural influences of the building come from France and Spain. Unlike the Tribune Tower, this building is still a group of office buildings. As a Chicago boy, I knew Wrigley. His gum was plentiful, and the Cubs played at Wrigley Field! William Wrigley Jr. purchased control of the Cubs in 1921 and renamed Weeghman Park to Cubs Park. In 1926, Cubs Park became Wrigley Field. Philip K. Wrigley assumed control after his father’s death in 1932. In 1977, William Wrigley took over the club after the death of his father, Philip. In 1981, the Tribune Company bought the Cubs from the Wrigley’s.
Growing up in Chicago, you’d hear the radio jingle, “Double your pleasure, double your fun with Doublemint, Doublemint, Doublemint gum.” Wrigley employed twins to appear on television and be heard on radio. Jayne and Joan Knoerzer, were the original Doublemint Twins. They were both professional singers and signed their contract with Philip K. Wrigley in 1959. Jayne and Joan showed fans how they could “double your pleasure, double your fun” by doing fun activities together, like playing tennis and riding bikes together. A new set of twins were hired in the late 1960’s when the first set of twins were getting married and having babies.
The Wrigley family dominated Chicago life, and the Wrigley Building stands as a constant reminder of their prominence.
Trump International Hotel and Tower
The Trump International Hotel and Tower is hard to miss. You also can’t miss the name. It was the fourth tallest building in the United States. It originally was planned to be the tallest in the world, but after the attacks of September 11, the plans changed so that the tallest building in the United States would be One World Trade Center, which replaced the twin towers in Manhattan. The Trump Tower is right on the Chicago River, so it’s hard to miss if you are in the neighborhood. This building was not around during our high school years.
The Prudential Building
When I was growing up in Chicago, the Prudential Building (now One Prudential Plaza) was the tallest building in Chicago. Completed in 1955, it was the first skyscraper built in Chicago since the Great Depression. Many other buildings were built in the 1960s that were taller than the Prudential Building. The tallest of these was the John Hancock building. Since that time, there have been plenty of taller buildings constructed, but the Prudential Building has remained in place and is easily seen by people on Michigan Avenue and from Millennium Park.
Absolutely Chicago Segway Tours
An outing with Absolutely Chicago Segway Tours is a very fun thing to do. The company has many tours to choose from and they’re all affordable. We chose the downtown and lake tour which took us through Millennium Park, Grant Park, The Field Museum, The Shedd Aquarium, the Adler Planetarium, and then back along Michigan Avenue.
The tour is about two and a half hours and includes some rest stops and lots of photo opportunities.
We were lucky to have Dan as our tour guide. He and the staff make sure you know how to safely operate a Segway. It was our fourth or fifth time on Segways, so we were well acquainted with the basics. Still, it’s good that they check everyone out so that all of us stay safe.
The route is about nine miles, and you are moving effortlessly around town and listening to things about Chicago you might not know about. This is a very good way to introduce yourself to Chicago and learn a few things about its history.
We’ve been on quite a few Segway tours over the years. It was fun to have the ability to see as much as we could of Chicago on a Segway, without sore legs and feet by the end.