You may not believe it yet, but yes, the time has come: you will soon take off for one of the most amazing cities in all of the United States. Chicago is waiting for you to marvel at its architecture, feast your eyes on the most authentic blues you’ve ever heard, and rock out to a Chicago Cubs game.
Planning a vacation? Looking for an adventure? Here are 101 crazy things to do before you die.
The famous “Windy City” has countless attractions that go through the history of the historical mafia Al Capone or the original Millennium Park, full of surprises.
Here’s a complete list with the 10 essential things you must do on a trip to Chicago. Get ready because… America is waiting for you!
Walk through Millennium Park
You’ve probably seen that giant stainless steel bean that decorates one of the most emblematic corners of the most famous park in all of Chicago on more than one occasion, haven’t you? It’s The Bean -or Cloud Gate, if you’re referring to its original name- an immense sculpture in the shape of a bean by the Indo-British artist Anish Kapoor, which has undoubtedly become the main attraction of Millennium Park.
Taking a picture of yourself in it will be something you can’t help but do before continuing your journey through the park, which stretches over 10 hectares in the heart of Chicago. And if you get lost on the trails, you’ll come across another of the surprises that Millennium Park hides: the Crown Fountain, designed by Spaniard Jaume Plensa. It is an interactive public artwork in which, in a black granite esplanade always covered with water, two opposite towers are erected in which digital videos are projected with the faces of Chicago’s neighbours. *Every time they open their mouths, a stream of water comes out of them.
And the icing on the cake is the incredible Jay Pritzker concert hall, designed by Canadian architect Frank Gehry, which hosts all kinds of outdoor concerts. Attending one of them when night falls and the universe of illuminated skyscrapers surrounds you is something you should not miss if you travel to Chicago.
Admire the view from the Willis Tower
And let’s go to the heights this time: no less than the 103rd floor of the tallest building in all of Chicago. We’re in the Willis Tower, known as Sears Tower until a few years ago, and from there you can enjoy the exhilarating views of the city that you won’t even be able to blink at.
Imagine having all of Chicago in miniature… Because, from the 413 meters high that you will find when you visit the Skydeck, the viewpoint of the Willis Tower, everything will seem tiny to you. Once you access it after the 60-second elevator ride, and depending on how daring you are, step up to one of the glass balconies that were added to the building in 2009 and from which you can experience absolute vertigo just by looking at your feet.
Delight in the view of Lake Michigan and the surrounding skyscrapers. And, if you’re lucky and the day is clear, you might even get to see the plains of Illinois or Wisconsin.
Enjoy its architecture
And since we are in its tallest building, it is time to talk a little about architecture, another of the great tourist attractions of Chicago. So we’re going to walk around the Chicago River, where skyscrapers follow one another in a continuous feast for lovers of beautiful buildings. And it’s not that they stand out for their historical value, no: due to the Great Fire that took place in Chicago in 1871 and that destroyed most of the city, almost all its buildings stand out more for their design and originality than for any other feature.
We will walk calmly as we turn our heads right and left, but, above all, upwards. In this way we will find some of the most emblematic constructions of the city.
For example, the Marina City, twin towers shaped like corn cobs that attract the attention of everyone who walks near them. They are located on the north bank of the Chicago River and have a small marina for pleasure boats, hence their name.
And we continue to 235 North Michigan Avenue, where the Tribune Tower stands, built in 1925 and home to the ‘Chicago Tribune’ newspaper. CNN also has its offices in this emblematic building of Neo-Gothic architecture that has a peculiarity that you will surely love: in its façade there are stones and tiles from other mythical buildings from all over the world. Some examples? You can see, walking around the building, pieces of the Taj Mahal, Hagia Sophia, Angkor Wat, Notre Dame Cathedral or one of the very pyramids of Giza.
And it’s time to have some fun, don’t you think? To do so, we’re going to the harbor, by the enormous Lake Michigan, of which you won’t see the end, neither wide nor long. There you will find Navy Pier, a large open-air shopping and leisure centre full of bars and restaurants, attractions, shops, theatres, museums and cinemas. It’s the place chosen by both the citizens of Chicago and the majority of travelers who come to the mythical “Windy City” to disconnect and limit themselves to walking and having fun.
Navy Pier is considered the oldest walk in the city. In its time it was a military training camp, although shortly after it adapted its current mission: that of public space that serves as a place of leisure and recreation for families and tourists.
Some of its most famous attractions are the “Ferris Wheel of Fortune”, renovated in 2016 and from which you get incredible views of the city and the lake. Also the mythical Children’s Museum or the Shakespeare Theatre. But, something you must not miss if you visit the Navy Pier, is to get on one of the boats that leave from this same place and make a tour of Lake Michigan. Getting that perspective of the city skyline is something you’ll always remember.
Get into the history of the mafia in Green Mill
And is there anything more related to Chicago than the figure of Al Capone? Probably yes, but what is clear is that the most famous mobster of all time left a great mark on his city and his history still reverberates in many corners.
So we go to the famous ‘Green Mill’, a legendary ‘jazz bar’ where the mafioso used to go with his people and where, even today, you can see the seat in which he used to sit, perfectly located to control both the front and back door if someone from the opposite side dared to go for him.
On the front, a fluorescent green sign welcomes you. Inside, the music plays while every detail makes you go back in time mentally and imagine how those dark nights were when gangsters were the owners and masters of the city, and when alcohol was forbidden and smuggled, transported through secret underground tunnels.
Little is left of that part of the story, but you can find a good corner and enjoy listening to a concert while having a drink… or two, why not?
Tour The Loop
And we’re going to kick up The Loop, as Chicago’s most central neighborhood is popularly known. Downtown, that place in the city where financial and commercial activity is concentrated. A district full of banks and businesses, shops, huge skyscrapers and where you can find some of the tourist attractions that you can’t miss on a visit to Chicago and that we have already mentioned in this article, such as the Willis Tower or Grant Park, where the Millennium Park is located.
But, this time, we will focus on learning about the lives of Chicago’s citizens. In seeing how it unfolds on any given day along its long avenues and streets. Walk down them, take a deep breath and experience the atmosphere you feel among the jacketed executives who rush along the sidewalks.
To understand the origin of the neighborhood’s name, The Loop, you’ll only have to look up. Probably the first thing you’ll see are the tracks of the elevated tram that runs through the entire district, and whose name is, indeed, The Loop. **This is the most popular means of transport in the city and has been running since the late 19th century between skyscrapers. **
Watch a Chicago Cubs game
How about we put on a Chicago Cubs cap and go do something as authentically American as attend a baseball game? The Cubs are the quintessential team in the city and, without a doubt, going to see them in action is one of the things you should do if you travel to Chicago.
Wrigley Field is their stadium, and if you arrive in time for the game, we suggest you take a walk around and get excited about the atmosphere. Hundreds of people wearing team colors walk to Wrigley in waves, a tradition that has been in place since the team’s founding in 1870. The surrounding streets, which are packed with bars, are filled with fans drinking beer and singing the praises of what’s to come.
Another option that is a little more expensive than attending the match from the stadium, but at the same time more fun, is to get a ticket for one of the roofs of the surrounding buildings that hold parallel parties. You can enjoy views of the stadium and not miss a detail of the game, while trying the open bar of food and drink that is included, a unique experience, we assure you!
Find the best skyline in Chicago
If you want to get an idea of the immensity of this city that has seen so many American films and series, you can’t miss one of its many viewpoints. So, that’s what we’re going to do!
And we’re off to the Adler Planetarium, which can be reached by crossing Solidarity Drive and from which you can get one of the best views of the whole city of Chicago, without a doubt. This area, much quieter and without the hustle and bustle of downtown, will allow you to stroll by the lake while admiring, in the distance, the huge skyscrapers of the city. The Willis Tower, with its huge antennae, will seem small in the distance, but it’s still impressive compared to the neighboring skyscrapers.
One option to tour this area of the city is to do it on a segway tour. Stopping by the planetarium and taking a souvenir photo with the entire city of Chicago behind you is a must.
Another of the viewpoints you can go to is Milton Lee Olive Park, from where you will get a panoramic view of the Chicago skyline, which is much closer but incomplete. You decide which one you want to take!
Let yourself be carried away by the best blues in the world
Meeting in the cradle of the blues… Can’t help but spend a night in one of his legendary clubs, don’t you think?
So we set off for ‘Buddy Guy Legends’, one of the most classic and where you can easily meet the legendary musician, owner of the first blues club in the world, what do you think?
As night falls, the most renowned performers of this musical genre take over the stage and the tables are filled with an audience that is unable to take its eyes off the show. Just by listening to the chords of any of the instruments your body will vibrate, your heart will start beating fast and your body will start moving to the rhythm of their notes.
Don’t hesitate for a second: feeling the Chicago blues is one of the experiences you should have in the city.
Route 66 begins
Did you know that the mythical Route 66 starts in the city of Chicago itself? That’s right, and the sign indicating the start of one of the most famous road trips of all time is right in the center of the city, at the confluence of Jackson Boulevard and Michigan Avenue. Why not go take a look?
Route 66 was part of the U.S. Federal Highway Network, beginning in 1926 and running between Chicago and Los Angeles. Some changes were made later, including moving the end – or the beginning, as you look at it – to Santa Monica instead of Los Angeles.
It was one of the most used routes by the immigrants who moved to the west of the country, and although today and since 1985 the road does not exist as such, still in some parts of the different states through which the route ran there are signs indicating “Historic Route 66”. One of the most authentically American experiences you should not miss. So, since you’re in Chicago… Why don’t you get in?
If you’re considering a trip to Chicago, you might be interested in these other articles:
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10 experiences you should have in the United States
The 10 most impressive viewpoints in the world
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