Chicago itinerary: the perfect 3-day trip

“My kind of town, Chicago is
My kind of town, Chicago is
My kind of razzmatazz
And it has, all that jazz
And each time I leave, Chicago is
Tuggin’ my sleeve, Chicago is
The Wrigley building, Chicago is
The union stockyard, Chicago is
One town that won’t let you down
It’s my kind of town”
Frank Sinatra

The excitement that Chicago inspired in me is hard to describe.
I have always got a thing for the United States: it is, quite simply, the country of my dreams, the one in which you imagine that your every wish will come true.

Chicago was my first encounter with my beloved States. When, after 8 long but pleasant hours of flying, I caught a glimpse of the city skyline at the end of Lake Michigan, I was moved. My heart was swollen with happiness and my eyes were wet, and when we passed over those towering skyscrapers a tear dropped.
Having one of the places you have always dreamed of in front of your eyes can have that effect… and if it is a city as beautiful as only Chicago can be, the effect is doubled.

Here we were supposed to spend 3 nights and 4 days, also planning a day in Milwaukee, having read everywhere that it would have been more than enough to visit the city… but no, don’t believe it, three days in Chicago are not enough to properly visit it. It is such a big and rich city that you need at least a week to discover all the most interesting parts of it without rush.
However, in three days you can get a good taste of it, see the most beautiful and unmissable, the most famous things, discover the heart of the city and… fall in love with it.

We landed in Chicago at O’Hare International Airport at about 2 p.m. (local time).
The line for security checks is long, especially if it’s your first time setting foot in the States and they have to take your fingerprints and retinal print (however, if you are a U.S. citizen or have a valid ESTA and have already been to America, it’s gonna take you a little less time).
O’Hare airport is about 25 km from the city.
The cab in my opinion is not the best alternative to get to downtown, because in addition to the high cost (we were charged $40/50) you risk getting stuck in the famous American traffic.
Instead, we opted for the little train that leaves from Terminal 3. The Chicago airport has 4 terminals, all connected by a monorail shuttle that runs every 2 to 3 minutes.
From Terminal 3 you have to go down to the parking lot (T floor on the elevator) and follow the “Train to City” signs. The ticket costs $5 and it takes about 30 to 40 minutes to get downtown (practically a few feet from Michigan Avenue).

Day one

Having arrived in the city late in the afternoon with the jet lag on our shoulders, between one thing and another, on arrival, we just managed to take a walk on the Magnificient Mile and have a drink at the Drake Hotel (which I told you about here), before collapsing exhausted on the bed.
The next morning we woke up super early thanks to the time difference that knocked us out of bed at 4 a.m., and our real exploration of the city began.
Before anything else, there was a dream I had wanted to fulfill ever since I had the plane tickets in my hands: to take a swim in Lake Michigan (so much so that I even listed it as one of the things not to miss in Chicago). This was the first thing we wanted to do, and I recommend doing it right at 8 a.m. when on the beach it’s just you, a couple of people walking dogs, and the Chicago skyline in the background.

Starting on Michigan Avenue, leave Millennium Park behind (for now) and cross the DuSable Bridge where you can see the University of Chicago’s Gleacher Center on your right and the Trump International Hotel&Tower on your left, and the Chicago Riverwalk is below you turn right onto East Illinois Street and from there continue straight until you find yourself in front of the famous Navy Pier. We preferred to go back there after the lake, but the Pier is definitelly worth a visit (even more so on a summer’s Wednesday afternoon, so after visiting and maybe a dinner at Billy Goat Tavern, you can watch the fireworks).

Right at the beginning of the Pier is the Chicago Children’s Museum, a three-story museum that encourages, through activities and exhibits, children and parents to explore, discover, create, and research. After the museum you will encounter the Chicago Shakespeare Theatre (a theater dedicated to the works of England’s most famous playwright and poet), the Ferris wheel and the beautiful Richard H. Driehaus Gallery of stained glass where in dark rooms you can admmire the works of Louis Comfort Tiffany (the son of the famous jewelry firm’s founder) who created true masterpieces with colors on glass.
Past the Pier, go through Jane Addams Memorial Park to land on a small beach of the clearest sand to which the park’s trees act as a gateway: Ohio Street Beach.
Here enjoy the clear, shallow water of Lake Michigan, the sunshine of the American midwest, and a view of part of the city skyline. It is absolutely worth it!

Go back across Jane Addams Park, take East Grand Avenue until you return on Michigan Avenue and walk for almost a mile (to the right, leaving Grand Avenue behind), there you will find the John Hancock Center, Chicago’s third tallest skyscraper at 100 stories and 344 feet high. You can go up (tickets are $20 per person) to the top floor to take in the most beautiful view ever of Chicago and Lake Michigan, but more importantly to experience TILT, an experience that will give you the sensation of “falling” on Michigan Avenue, and of flying over the street (you can read our dedicated post). Unique!
Walk back down the street to return to Michigan Avenue, also called the Magnificient Mile, and right at the intersection with East Illinois Street, take a closer look at the Tribune Tower (the very one from the famous Chicago Tribune): on its walls are pieces of 149 historic buildings from around the world, brought in by the newspaper’s correspondents. From Fort Alamo to the Colosseum, from the Great Wall of China to Pompeii, from the pyramids to Westminster, it’s like a world map!
Resuming the walk, just before the DuSable Bridge you will find Wendella Boats, which organizes boat tours including the ever-present Architecture Tour.
After the fire that destroyed downtown in 1871, Chicago became the headstone of a movement and a school of architecture that gathered two generations of architects who transformed the city into a place of innovative design and architectural avant-garde (not coincidentally, later Frank Lloyd Wright opened his studio here and worked on several works). The 75-minute tour, navigating along the river, leads you to discover with the help of an expert guide more than 100 years of architectural innovation and its importance (tickets cost $35.50 per person).
At the end of the tour go back to Michigan Avenue and continue until, on your left, you see Millennium Park, one of the world’s largest public parks, opened in 2004.
You could spend hours there! It is a beautiful park where you can relax, listen to music (including live music: we caught the Open Rehearsal of the Grant Park Music Festival), and play in the fountains.
There are four main things to see here:

  • The Cloud Gate: the famous Bean on which the entire surrounding city is reflected. Despite the cute nickname, it is a true work of art, inspired by liquid mercury, by the artist Anish Kapoor. Created with 168 stainless steel plates fused seamlessly with not even the slightest welding sign visible from the outside. Many tourists pass by here mainly to admire its reflections and take cute photos, but… I would take the opportunity to admire its perfection, the way the steel curves, and the originality of seeing no welds in a work that weighs over 100 tons!
  • The Crown Fountain: the fountain made with two glass blocks about 50 feet high, on which are showed the faces of more than 1,000 Chicagoans who lent their image for the work.
  • The Laurie Garden: a distinctive garden, beautiful and colorful in all seasons. In summer there are also free tours every Thursday, Friday and Sunday.
  • The Jay Pritzker Pavilion: is the one I liked best in the whole park, I admit. Home to outdoor concerts, it has a 36-meter-high stage with a curved canopy of sails that extends over all 4,000 seats and more.

The first day ends here, so you have time to enjoy each place with the calm and attention it deserves. But to end the day as true Chicagoans, you can go for a Deep Dish Pizza at Giordano’s!

Day two

The next day, the second day spent discovering this amazing city, start by going back near Millennium Park, on East Washington St to be exact, where you will find the Chicago Cultural Center, one of the largest art collections in the United States: Carrara marble entrance, Tiffany stained glass dome… it also hosts more than 700 free events each year, and it is the place where the city’s mayor receives important people.
Once you leave, you will find almost in front of you Grant Park, in the middle of which you will see the world-famous Art Institute of Chicago, which opened in the very same place in 1893. It collects works by artists such as Cezanne, Correggio, Degas, Gaugain, Modigliani, Monet, Picasso, Toulouse-Lautrec, Van Gogh… and many, many other nineteenth-century artists, as well as modern and contemporary art. It is the second largest art museum in the United States!
A proper visit (and it is definitely worth it) is sure to take more than two hours, tickets cost $25 (free admission under 14) and the museum is open daily from 10:30 a.m. to 5 p.m. (until 8 p.m. on Thursdays).
As you leave the institute, cross Michigan Avenue, continue down on it (to understand, leaving the Art Institute go on your left) and a few feet later you will find the Rookery Building, one of the oldest and most beautiful buildings in all of Chicago, an architectural masterpiece. Created by architects Daniel Burnham and John Root, with the touch of Frank L. Wright, it has a very bright lobby that you can visit for free, or take one of the tours that reveal all the stories and anecdotes behind this magnificent building.

Exit this building and head back toward the Art Institute, just across the street from the entrance to the institute is Adam Street, and here you will find what we were looking forward to see: the sign indicating the beginning of Historic Route 66. An extraordinary thrill to see it in person, the kind of thrill that only fulfilled dreams can provide.

Continuing along Adam Street for about half a mile, on your left you will find another Chicago landmark: the Willis Tower (the entrance, however, is on Wacker Drive) and its Skydeck.
With its 103 stories (the elevator ride takes 90 seconds in which a video is shown with some information about the tower and its history) and 1453,41 feet high (1729 counting antennas), it was the tallest tower in the world until 1998 and is visible from four states: Illinois, Indiana, Michigan and Wisconsin. Admission costs $22 ($14 for ages 3 to 11) and takes you up to touch the sky, admire the whole of Chicago from a 360-degree view from above, and have it right under your feet thanks to its glass balconies, the tower’s highlight. An amazing sight, on that balcony I felt like I was flying!
(Although from the photo below it looks more like I’m panicking… let’s just say it is really impressive, but that feeling quickly passes!)

after this you can call it a day, perhaps eating something at one of the city’s famous blues clubs!

Day three

Onthe third day, once you have already visited the heart of the city and its must-sees in the previous days, I recommend a treat: Andersonville.
It’s an area on Chicago’s North Side that began as a fishing village founded by Swedish immigrants. It is very quaint, colorful, and stands out for many reasons: it is the center of the city’s LGBT+ community, there are no international chains here but only stores and restaurants (among the best in the city by the way) of independent private individuals selling typical products that recall the Swedish origins of the place, and finally its quirky, lively and multicultural atmosphere. Also located here is the American Swedish Museum, a museum dedicated to the history of Swedish immigrants with an art gallery, a children’s area, and a store selling Swedish crafts.
The best and most peculiar place in the area is the Andersonville Commercial Historic District (on North Clark Street), where the area’s historic sites and quaint stores are located.
To get here just take the bus 22 from Michigan Avenue (bus fare is $2.25) and the trip takes about 40 minutes.

Back to downtown, you can go see the MoCP – Museum of Contemporary Photography, one of the most beautiful photography museums in the world (we missed this one, and you have no idea how disappointed I am for not being able to see it! As usual though, I think this gives me reason to return to Chicago as soon as possible!). It is located at 600 Michigan Avenue (across from Grant Park, two streets past the Rookery Building) and brings together exhibitions, events, and reviews that celebrate the best artists in modern photography. A must-see for any traveler and lover of photography!

Visiting these two will take you most of the day, but if you have time there is still so much to see in Chicago: for example, you can go, starting at MoCP, visit Buckingham Fountain, which is at the end of Grant Park right across from the museum, or the Shedd Aquarium or the beautiful Adler Planetarium (also in the area, on Northerly Island).

Chicago is one of the most vibrant and interesting cities in the United States, a fascinating city that is hard not to love. I hope this itinerary will give you a chance to appreciate it as much as we do, we just can’t wait to go back there to see more of what we have already seen and discover what we yet have to see.
And to go back there again, and again, and again….

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