I want to start this article by saying that The Windy City is windy indeed. I visited Chicago for the first time last year, in December and unfortunately, the weather wasn’t nice at all.

We (me and my boyfriend) spent two days in Chicago, but we could only enjoy the second one to the fullest. For that matter, I’m going to give you a tip from now: try to visit Chicago in spring or summer!

Even autumn can be a good idea, but winter is certainly not unless you really want to experience Chicago during the holidays.

    Exploring Chicago was a lot of fun! I loved the architecture of the buildings, the clean streets, the beautifully designed parks, but I guess my favorite was the Riverwalk.

By the way, did you know that Chicago is the birthplace of the American skyscraper? I honestly had no idea, but I did my homework and tried to find out as much as possible about this fascinating city before I went to visit it.

Chicago Riverwalk


    The City of Big Shoulders (one of the many nicknames that Chicago has) is located in northeastern Illinois, on the shores of Lake Michigan.

    There was one event that completely changed the course of the city’s evolution. A big part of the actual architecture was rebuilt in the late 19th century after the Great Fire of 1871 wiped out much of the historic center.

However, Chicago succeeded in becoming again one of the most beautiful cities in the US, despite the tragic events that I’ve mentioned.

     At the present time, Windy City has plenty of attractions for everyone. In this post, I will mention the 10 that I liked most, during my visit. Here we go…

TOP 10 things to do in Chicago

     1.Cloud Gate aka The Bean:

     Being located right in the heart of downtown, it’s impossible to not spot it. The Bean is a neat piece of architecture, designed by Anish Kapoor. The iconic construction is made of 168 highly polished stainless steel plates and has a shape inspired by liquid mercury.

Most tourists come here to capture a beautiful reflection of Chicago’s skyline. No wonder why is always crowded around it! For the record, its weight is not less than 100 tons.

Find here the best hotels in Chicago. 

Chicago The Bean Cloud Gate

Chicago The Bean Cloud Gate

Chicago The Bean Cloud Gate

Chicago The Bean Cloud Gate

     2. Millenium Park:

     Like all of Chicago’s architectural style, this park is truly spectacular, as well. Home to the Bean, Lurie Gardens, Crown Fountains and lots of outdoor art displays, Millenium Park has it all.

One of my favorite pieces of architecture that I found here was the Pritzker Pavilion, used for outdoor concerts. I think it has a great design, so different than anything I’ve seen before. In addition, the park represents a very pleasant way to walk around.

Millenium Park Chicago


     3.Chicago’s Riverwalk:

     As I said at the beginning of this article, this is my favorite activity in Chicago. You can either choose to go on a free guided walking tour or to go by yourself.

In my case, I chose the second option, of course, accompanied by my boyfriend. Riverwalk is one of the best aspects of this city, a place that I’m sure both tourists and locals love it.

If for any reason, you don’t go on a river cruise, this is the best option to admire the architecture of the most iconic skyscrapers, and not only, in the city. 

⇒ Also read: What to visit in San Francisco in less than a day

Riverwalk Chicago

Riverwalk Chicago

Riverwalk Chicago

Riverwalk Chicago

Riverwalk Chicago

     4.The Art Institute of Chicago:

     This museum will successfully compete against the best art museums in the world. Located on Michigan Avenue, the Art Institute is the second largest museums in the US, being visited by over 1.5 million people annually.

Inside, you’ll find more than 300 000 works of art that will probably take your breath away for a whole day.

Art Institute Chicago

     5.Ice skating in Millenium Park:

     Unfortunately, skating here is only available in the winter season. Personally, I would say that is a big rival of the Central’s Park rink in Manhattan. Moreover, here the admission is free. For daily hours of operation, you can check the website

Ice Skating Chicago


     6.Willis Tower and the Sky Deck:

     Willis Tower, previously named Sears Tower, was the tallest building in the world for over 25 years.  If you wish to have a unique and at the same time a terrifying perspective of the city, then you must visit the sky deck.

The view from up there is simply stunning.  The line was pretty long, but eventually, we could make it to the top right before the sunset. Imagine admiring the panorama of the city from the 103rd floor, while sitting on plain glass.

It took a year of engineering and six months of construction to create the 4 boxes. Also, 4 states are visible from that height: Illinois, Indiana, Michigan and Wisconsin. 

Overall, I believe that Willis Tower is one of the most popular tourist destinations. As a fun fact, the tower was designed by an advertisement for a package of cigarettes.

Willis Tower Chicago

View from Willis Tower Chicago

Willis Tower Chicago

sky deck chicago

     7.Michigan Avenue:

     Are you a shopping addict? Then this is heaven for you. Michigan Avenue is Chicago’s most popular shopping street. However, the most famous section of it, it’s called Magnificent Mile, a place where you will find many brands and high-end shops.

In my opinion, this avenue is also a great place to walk around and feel the vibe of the glamorous city.

Find here the best hotels in Chicago. 

Michigan Avenue Chicago

Michigan Avenue Chicago

Michigan Avenue Chicago

Michigan Avenue Chicago

   8.Water Tower:

     After you have finished your shopping, you must visit this stunning and nonconformist building. It literally looks like a small European gothic castle. The Water Tower is the second-oldest water tower in the United States, constructed in 1869 out of limestone blocks.

Water Tower Chicago

     9.Navy Pier:

     Head down to the shoreline of Lake Michigan and you will find this famous landmark. The Navy Pier is home to the Chicago’s Children Museum, Pier Park, IMAX Theatre and of course, the Ferris Wheel.

Moreover, the city’s 4th of July and New Year’s Eve fireworks take place here every year.  The Ferris Wheel can also be a great option if you wish to have one of the best views of the city.

Navy Pier

     10.Chicago skyline:

    After seeing New York, Miami, Los Angeles and San Francisco, I have to say that Chicago has one of the best skylines in the US. However, it is officially ranked as second best, so I can’t agree  more with that ranking (NYC will always be number 1, no offense :D).

I’m sure you will want to get the best views of Chicago’s skyline, so I’m going to share my favorite spots to help you. These are, in no particular order: the Navy Pier, Riverwalk, Millenium Park and of course, the view from above, on the 103rd floor of Willis Tower.

     The TOP 10 tallest buildings in Chicago are Willis Tower, Trump International Hotel, and Tower, Aon Center, John Hancock Center, Frankin Center, Two Prudential Plaza, 311 South Wacker Drive, 900 North Michigan, Water Tower Palace, and Aqua Tower.

Chicago Skyline

Chicago Skyline

Chicago Skyline

Chicago Skyline

Chicago Skyline

     Other attractions to consider:

  • 360 Chicago- John Hancock building
  • Boat tours
  • Lincoln Park Zoo
  • Oak Street Beach
  • Explore the neighborhoods
  • Shedd Aquarium

     Bella’s tips:

1. The parking is extremely expensive. If you check into a hotel, make sure you’ll find one that already has parking included and rather use the subway.

2. Try to get to the top of Willis Tower at least an hour before the sunset in order to admire the breathtaking panoramic views. You must see them in the natural light, but also after is getting dark when you can admire the city being lighted.

3. Chicago is named The Windy City for good reasons, so you’d better get some extra layers because it can get really cold outside and extremely windy.

4. The public transport is very good and pretty cheap so it makes no sense to spend money on renting a car and parking

5. I advise you to visit the Bean early in the morning when it’s not that crowded yet. We went there around 1 pm, and it was kind of hard to take some good pictures.

6. If you are a student, don’t forget your ID at home because you can get a discount for some of the attractions. For example, for the Art Institute.


Public transport Chicago


Public transport Chicago


    Fun facts about Chicago:

  • The design of Willis Tower was inspired by an advertisement for a package of cigarettes
  • Cloud Gate weights 1000 tons
  • The world’s first skyscraper was built in Chicago in 1885 (Home Insurance Company)
  • More than 52 million people visit Chicago annually
  • Walt Disney was born in Chicago in 1901
  • Chicago River is the only river in the world that flows backward
  • The first Playboy Mansion was in Chicago
  • The Ferris wheel was also invented in Chicago in 1893
  • Chicago invented the deep-dish-pizza
  • Historic Route 66 began in Chicago