From the skyline glittering with lights and non-stop traffic, it may look like New York City, but it’s not. It’s the city that boasts some of the tallest skyscrapers in America, the Mid West city where every building has a unique story, the one with the most beautiful downtown in the entire United States, perhaps. You’ll walk around with your nose perpetually in the air and you’ll feel like you’re in a movie from the future, expecting to see flying cars in the sky. To get an idea of what to do in Chicago without missing out on the highlights, follow me and take note: I’ll give you something much better than a top ten!
Best things to do in Chicago
Even though it is a metropolis, Chicago’s main attractions remain in the city center, the Loop, named after the elevated subway that outlines the city, which we will talk about in the upcoming article “how to get around Chicago”. Not everyone knows that the mother of all roads, Route 66 starts right in Chicago’s Loop (to be precise, on the north side of Adam Street, between Michigan Ave and Wabash Ave). If you’ve already got an idea of the best time to visit Chicago, here’s what to see in the city.
Millennium Park is Chicago’s most precious jewel, certainly a showcase for modern architecture as it houses masterpieces such as the Pritzker Pavilion, a majestic silver structure that hosts many free concerts every year starting at 6:30 p.m., and the BP Bridge, the bridge that connects the park to the Daley Bicentennial Plaza across Columbus Drive; crossing it you can admire the beautiful skyline of the city that is reflected in Lake Michigan.
Another famous work is “The Bean“, as Chicagoans call it, the Cloud Gate, a smooth silver sculpture weighing more than one hundred tons with an unmistakable bean shape. The Crown Fountain also attracts many visitors: it is a fountain that projects the faces of citizens by making water flow from a slot in the screen: the mechanism is so effective that it seems that the faces really spit water from their mouths and children are fascinated so much to linger for almost an hour in front of the fountain!
Grant Park and Millennium Park are home to countless places of interest and outdoor activities, such as free gymnastics classes or ice skating. A true feather in the city’s cap.
The skyscrapers of Chicago
Chicago is a pilgrimage destination for lovers of architecture. Just think that right here is the tallest building in the United States (or rather, it was from 1973 to 1998), the Willis Tower (the former Sears Tower): 110 floors, 1453 feet high. Only the Pentagon has a larger surface than this skyscraper. Walking on the Skydeck on the 103rd floor will make you feel like you’re walking on clouds.
But not only the Willis, but also the Chicago Board of Trade will leave you open-mouthed with its art deco style, as well as the Rookery (a building that owes its name to the pigeons that used to roost there). Frank Lloyd Wright has also had his hands on this skyscraper, as he was responsible for the renovation of the atrium. I can’t help but recommend a visit to the Monadnock Building which is the result of two buildings in one: the north side is the older one while the south side has a modern style.
The list would be endless, to learn more about the architectural sights you should take advantage of the Go Chicago Pass, which includes a tour of the Chicago Architecture Foundation (or the Chicago Architecture Cruise which I talk about below).
After you’ve taken your kids to see the tallest skyscrapers and a few architecture tours, to make it up to them, you can give them this gift: choose one of these destinations, the museum, the aquarium, or the planetarium.
The Art Institute of Chicago, the second largest art museum in the United States, is a must-see. Located in Grant Park (a green area between the Loop and Lake Michigan), you’ll find works from all over the world; the collection of Impressionist paintings by George Seurat is fundamental, but there are also canvases by Picasso, Miro, Cézanne, Chagall, Monet, Renoir… the list is long, it definitely takes less time to go there than to name all the artists present!
At the Field Museum, in addition to mummies and stuffed monkeys, children can see the majestic creatures of Jurassic Park with their own eyes. In fact, the museum is home to the largest specimen of Tyrannosaurus Rex: Sue.
If it’s the ocean that fascinates you, you can come face to face with white dolphins, whales and sharks at the Shedd Aquarium. Finally, if you really don’t care about animals, Chicago offers you the stars: at the Adler Planetarium, on the first Friday of the month, the staff offers you their telescopes to observe the sky.
Remember that I recommend the most famous (and most worthy in my opinion) stops, but the city is so full of things to do and see that you’ll have to arm yourself with patience and make a selection and – alas – cross something off the list, unless you want to stay for a month.
From the list, however, you can’t cross off Navy Pier, what was once the main pier. You could call it the focal point of Chicago, the hub, the terrace, you name it. From here you can use up your cell phone memory taking pictures of Chicago’s unique and inimitable skyline (take note: there are fireworks on Wednesdays and Saturdays), take a ride on the Ferris wheel, go to one of the nearby beaches on Lake Michigan, browse the stores and restaurants and enjoy your trip to the fullest.
The Blues Capital of the World
“It’s 126 miles to Chicago. We have a full tank of gas, half a pack of cigarettes, it’s dark, and we’re both wearing sunglasses.”
(The Blues Brothers)
What city is the home of music more than this one? This is where the Blues was born, this is where a genre was created that changed the history of music and much more thanks to Chess Records, a small record company founded in 1947 that discovered artists such as Muddy Waters, Etta James and Chuck Berry. To spend an unforgettable evening here, you are spoiled for choice. The city is teeming with blues clubs such as the historic Buddy Guys’ Legend, the Kingstone Mines or the Blue Chicago: you expect the Blues Brothers to pop up at any moment. In addition to the clubs, if you’re still not satiated with the blues, Millennium Park hosts the Chicago Blues Festival every June.
How many days to spend visiting Chicago
As you may have guessed, Chicago is overflowing with places of interest. It takes at least three days to visit, but five would be better. In three you can stay in the central district and enjoy the attractions of the Loop, but with five you can experience what it really offers, such as a concert in Millennium Park or in one of the famous blues clubs, or visit the Architecture Foundation. Keep in mind that Chicago is like a second New York, so if you’re thinking of “popping in”, think about the main attractions.
The good thing about Chicago is that it is full of attractions, the bad thing is that it is not exactly cheap. How can you remedy this problem? We have told you about the different types of Chicago Passes, that you can use to not only save money but also to get an idea of what the must-see things are in the Windy City.
Places to stay in Chicago
Good question. The answer is: it depends on you. If you’re only planning to spend three days in the city, you’ll want to stay in the Loop, but if you want to explore the city, you can also stay in a less central area, like the South Side (and therefore cheaper). Think about it, make a list of the things you have decided to visit and then decide which is the best place, maybe by reading our guide on where to stay in Chicago, where we suggest not only the most strategic areas but also some interesting accommodations.
Among the many things to do in Chicago, we can suggest some tours with a list of attractions included: the first is definitely a trip on the Hop On Hop Off Bus, the legendary red bus that crosses the Windy City in comfort. One of the best ways to visit places of interest for the whole family.
If, on the other hand, you have come to the city of skyscrapers to relive the roaring twenties, well then this is just the tour you are looking for: a dinner and show at Tommy Gun’s Garage, where gangsters and Charleston music will keep you company to give you a real “Gatsby” evening!
The last one is the half-day Grand Tour: a 4-hour bus trip to visit the length and breadth of Chicago, from the South Side to Grant Park, from the Planetarium, the Art Institute and Orchestra Hall to end up in President Obama‘s neighborhood!
But that’s not all. For an infinite city, infinite ways to discover it. With this tour you can visit the city in half a day, first by bus and then by cruise. If, on the other hand, you only want to experience the cruise on Lake Michigan, these other two proposals will satisfy you:
- a tour to admire the Chicago coastal architecture, touching on more than 40 stops, including John Hancock Center, the Wrigley Building, Aon Center, Willis Tower (Sears Tower), and more.
- a slightly more romantic cruise, including a buffet dinner and fireworks to follow. What more could you want?
Chicago and the cinema
The architecture, the Blues, the museums, Millennium Park and the cinema. Chicago is an open-air movie set, if you love cult movies you will know that here, in addition to The Blues Brothers, The Untouchables was also filmed (why not also take a ride in the beautiful Central Station to relive the scene in which Kevin Costner from the top of the stairs kills Al Capone’s gansters?). For the record I must inform you that the romantic comedy My Best Friend’s Wedding was also filmed in the station. You should know that my movie pills will haunt you in every article, I swear I will try to contain myself!
I’ll stop here but I hope I’ve intrigued you because visiting Chicago is always a very good idea, you’ll discover so many attractions and all kinds of places of interest where you’ll leave your heart and a little bit of your wallet (but it’s worth it!).
One final tip…
If you want to learn about Amish culture, visit the village of Shipshewana in Indiana: it is just a couple of hours away from Chicago.