Chicago: My 10 absolute highlights

Illuminated Chicago skyline

Chicago has always held a similar fascination and attraction for me as New York City does. But when I really stood in this stunning city in the middle of the canyons, my mouth simply remained open in amazement! In this post I'll show you my personal ten highlights in the "Windy City" from the best viewpoints to the most interesting sights. 🙂

This article was last updated on 02. April 2019 update.


Time of travel: May 2010 (3 days, 3 nights)
Getting there: By rental car from Cedar Point amusement park in Sandusky to Chicago (approx. 4:45h)
Accommodation: Sofitel Chicago Magnificent Mile ***** (20 E Chestnut St, book hotel*): Impressively beautiful and stylish hotel in a perfect location in the middle of downtown Chicago. The Magnificent Mile, Hancock Tower, and other landmarks are within walking distance. Chicago subway station (Red Line) two minutes away. Very spacious rooms, comfortable beds, lots of storage, stylish bathroom with super shower, great views of the skyscrapers all around. WLAN with good speed, breakfast not booked. Recommendation? YES
You can search and book more beautiful hotels in Chicago here*.


*The links marked with an asterisk in this blog article are so-called affiliate links. If you book something through these links, you support my work and I receive a small commission. There are no disadvantages for you.

Buckingham Fountain and the Chicago skyline at night

The attraction of Chicago

When my girlfriend and I were planning our trip to the eastern U.S., the focus was still on Niagara Falls, in addition to New York and Washington. We also wanted to visit one of the infamous roller coaster parks – Cedar Point in Sandusky, a four hour drive from Niagara Falls. This opened up another opportunity that we did not want to miss: Chicago!

Well known from movies and television

Indeed, from Cedar Point amusement park (which I'll introduce you to once in another post), it's once again only a four-and-a-half-hour drive to arrive in the city on Lake Michigan. Chicago is familiar from numerous series (u.a. Emergency Room, Married … with Children, The Good Wife) and really made me want to explore it in person through various cityscapes on TV.

Chicago, "the Windy City

The skyscrapers not only form impressive street canyons, but also one of the most beautiful skylines in the USA, as you can see from my lead picture. The location directly at the huge Lake Michigan gives Chicago not only quality of life, but also often generates strong winds – hence the nickname "Windy City".

Three days as a tight margin

Due to the tight program in the other cities, my girlfriend and I unfortunately only had three days in Chicago, which is already a very short period of time. Thus we had to concentrate on the most important points in the city, which interested us both. These are presented below in my personal order of preference!

Other stops on this trip

The stay in Chicago was part of a two-week trip through the USA. My girlfriend and I also visited New York, Washington and Niagara Falls, the travelogues you can find below or. will follow soon!

Itinerary: Vienna -> New York (Austrian Airlines flight) // New York -> Washington, D.C. (JetBlue flight) // Washington, D.C. -> Buffalo Niagara (United flight) // Buffalo Niagara -> Chicago (rental car) // Chicago -> New York (JetBlue flight) // New York -> Vienna (Austrian Airlines flight)

How best to soak up the atmosphere of a metropolis? Right, from above! The skyline of Chicago is certainly one of the most beautiful in the U.S. – and this is really clear, for example, from the observation deck 360 Chicago (875 N Michigan Avenue). By the way, the attraction used to be called John Hancock Observatory and was named after the skyscraper's name. With the train you get fast to the 94. From a height of 300 meters you can look into all directions.

View in all directions

I recommend you to go up about an hour before sunset to admire the surroundings in daylight as well as in the wonderful evening light with the illuminated buildings. A ticket (online purchase here*) costs USD 22,- (EUR 19,40), additionally there is a thrill to experience with the attraction TILT for USD 8,- (EUR 7,-) extra charge. Leaning against a glass wall, it is tilted outwards by 30 degrees and you look diagonally into the abyss – nice, but in my eyes also not really exciting. The view alone is excitement enough! 😉

View from the platform 360 Chicago in the John Hancock Tower View from the platform 360 Chicago in the John Hancock Tower View from the platform 360 Chicago in the John Hancock Tower on the Navy Pier and Lake Michigan View from the 360 Chicago platform in the John Hancock Tower

"Love and marriage, love and marriage, go together like a horse and carriage, …" When you stand in front of the Buckingham Fountain, many of you will immediately think of the TV series "A terribly nice family". "Married … with Children") and its theme song by Frank Sinatra. This is what happened to me and it was a strangely touching feeling to actually see this place with my own eyes! The big fountain, whose official name is actually Clarence F. Buckingham Memorial Fountain reads, stands in Grant Park (see also item 4)

Strong photo motif in Chicago

By the way, it is modeled on a fountain from the gardens of the Palace of Versailles and scores with lovingly designed sculptures. The skyscrapers of the skyline line up in the background and together with the fountain form a fantastic photo motif. It is in operation only in the warm season from April to October, in between it is unfortunately not a really attractive object. Make sure you visit in the evening, because then the Buckingham Fountain shines in great colors and there is also a musical background to enjoy.

Buckingham Fountain and Chicago skyline Panorama of the Buckingham Fountain and the Chicago skyline

A small part of the huge Grant Park (see point 4) is the Millennium Park, where two interesting objects are located, which seem to have built in real tourist magnets. 😉 The 100-ton sculpture Cloud Gate by British artist Anish Kapoor resembles a giant bean and is therefore often just called "The Bean". The artwork consists of 168 stainless steel plates, which are seamlessly welded together and highly polished. This creates fascinating reflections of people and the skyline on the surface. You can imagine that something like this always attracts the crowds – so if you want to see the thing in peace, better come early in the morning.

The Crown Fountain

The second work of art called Crown Fountain is also something special and I liked it enormously. Two 15 meter high towers with LED elements face each other, separated by a large area of reflective granite stones. On the LED surface, the portraits of about 1.000 people from Chicago projected, their mouths spewing water at irregular intervals. A shallow pool of water forms on the granite surface, reflecting the skyline. Especially in hot weather, the artwork is also a popular playground for children to cool down. I think it's really great how art and the viewers come together here!

Cloud Gate (The Bean) in Chicago's Millennium Park Cloud Gate (The Bean) in Chicago's Millennium Park Cloud Gate (The Bean) in Chicago's Millennium Park Crown Fountain in Chicago's Millennium Park

Grant Park is a 1.3 km² park directly on Lake Michigan and a perfect oasis for recreation. The park is home to numerous attractions such as Millennium Park with its two famous works of art Cloud Gate and Crown Fountain (see point 3), Buckingham Fountain (see point 2) and the Art Institute of Chicago. In Millennium Park, the Jay Pritzker Pavilion by star architect Frank Gehry, where open-air concerts of all musical genres are regularly held, is also visually striking.

Unobstructed skyline views

If you follow the park southward, you will also notice the many public baseball practice fields, which are gratefully accepted by the population. In the distance, you're not looking at a practice field, but at Soldier Field Stadium, which is a monster in terms of construction and over 60 stories tall.000 people. Personally, however, another circumstance struck me very positively: from Grant Park you have an almost unobstructed view of a large part of Chicago's skyline!

Jay Pritzker Pavilion by star architect Frank Gehry in Chicago Sunset and Chicago skyline

"The Loop" is the name given to downtown Chicago. The downtown area of this lively metropolis is bustling with activity among the dozens of skyscrapers, and a stroll here is an absolute must for visitors. The name comes from the end of the 19th century. A funicular railroad used to run around downtown in the early twentieth century. Very interesting is the mixture of historic and modern skyscrapers as well as the fact that despite the cramped conditions there are always places that allow a generous view of the surrounding buildings. You can get very special views of downtown by taking the elevated train eight meters above street level!

The Magnificent Mile

One of the highlights in the Loop is the Magnificent Mile boulevard. This is the northern part of Michigan Avenue, where you can see the neo-Gothic Water Tower – one of the oldest buildings in the city and one of the few to survive the Great Chicago Fire of 1871. Very impressive are also the Wrigley Tower from 1924 and the neighboring Tribune Tower from 1925. Don't miss a detour to the Chicago River, which leads to the city's main drag. Patrick's Day is colored green.

Water Tower on Chicago's Magnificent Mile Skyscrapers on Chicago's Magnificent Mile Wrigley Tower and Tribune Tower on Chicago's Magnificent Mile Green colored Chicago River Elevated train (Chicago Elevated) in the Loop

Besides the observation deck 360 Chicago presented in point 1, there is a second one in downtown, the Skydeck Chicago. You may be wondering if another visit to a skyscraper makes sense and is different from the other one? From my point of view it is not a must, but I would do it again anytime! The Willis Tower (formerly the Sears Tower) is the second tallest building in the U.S. after the One World Trade Center in New York (as of 2019) – this alone is a reason to visit the observation deck at 412 meters, because you don't often get that high in cities.

Views of the sea of lights

The views are also absolutely fantastic and allow you to take spectacular photos home with you. In addition, there are small glass niches where you can look hundreds of feet down into the abyss – oppressive and not for the faint of heart! 😉 I recommend you also at Willis Tower to come one hour before sunset to catch all the light moods. The ticket costs USD 25,- (EUR 22,-), it is best to buy it online* in advance to avoid having to queue at the box office on site.

Glass floor in the Skydeck Chicago (Willis Tower) Sunset seen from the Skydeck Chicago (Willis Tower) View from the Chicago Skydeck (Willis Tower) Skyline of Chicago and Lake Michigan seen from Skydeck Chicago (Willis Tower)

Navy Pier is one of Chicago's most popular attractions, with nine million visitors annually. A one-mile stretch of rides, restaurants, and cultural venues are located here. Personally, I'm not a big fan of excessive hustle and bustle, but you definitely have to check out Navy Pier. In the summer months there are fireworks twice a week on Wednesday and Saturday late in the evening – but unfortunately our visit was too early to see them. The exact dates and more info about the attractions can be found on the website

Large amusement mile

We skipped the enchanting Ferris wheel, which I regret a bit in retrospect. You pay USD 18,- (EUR 15,80, with online purchase USD 16,- resp. EUR 14,-), but for that the view of the skyline must be indescribable! Besides the northern entrance to Navy Pier, a short trip to Lake Michigan is also worthwhile, because there you will find a small city beach, Chicago Beach. 🙂

Fountain in front of Navy Pier in Chicago Ferris wheel on the Navy Pier in Chicago Skyscrapers in front of Navy Pier in Chicago Skyline and Chicago Beach

We didn't see a show and couldn't explore the inside of the building – but still the Chicago Theatre ( 175 N State St ) is one of my must-sees in the city, at least from the outside! The theater, built in 1921, was originally named Balaban and Katz Chicago Theatre, named after the famous theater group. Since 1983 it has been an official landmark of the city and is still a popular venue today. I would have liked to see the dozens of lights in full illumination in the evening, but also during the day the neo-baroque facade radiates a very special atmosphere. Be sure to stop by and be amazed!

Exterior view of the Chicago Theatre Engine 42 of the Chicago Fire Department (CFD) in front of the Chicago Theatre

The Lincoln Park Zoo is located a bit outside of downtown in the north. It can be reached either by a long walk – but we chose the quick approach by bus. From downtown Chicago, lines 22 and 36 go almost directly in front of the zoo (Clark station& Armitage). The entrance to the zoo is free of charge, which makes the time expenditure worthwhile again. Lincoln Park Zoo, opened in 1868, is home to more than 1 million animals.100 animals, including gorillas, polar bears, big cats and many more. A visit is certainly not a must, but I found a short distraction from the big city very pleasant.

Gorilla at Chicago's Lincoln Park Zoo Polar bear in the Lincoln Park Zoo of Chicago Meerkats at Chicago's Lincoln Park Zoo

My last highlight refers to Saint James Chapel ( 835 N Rush St ), but basically this tip can be considered representative for many worth seeing churches in Chicago. We passed the church shown in the following photos only by chance, but the colorful and enormously detailed stained glass windows amazed us in disbelief. Two more beautiful sacred buildings I would like to recommend to you, even though we didn't have time to visit them: the centrally located Holy Name Cathedral ( 730 N Wabash Ave ) and the Saint John Cantius Church ( 825 N Carpenter St ) west of downtown.

Saint James Chapel in Chicago Saint James Chapel in Chicago Saint James Chapel in Chicago


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