TOP 10 things to do in Chicago

Even if you’ve been there a few times, there are still plenty of things to do in Chicago. It’s the type of city where things are continuously changing, and something new is always coming up.

Also, Chicago is about listening to the waves while gazing up at the skyscrapers. What could be greater than that?


 I want to start this article by saying that The Windy City is windy indeed. 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.


There are so many amazing things to see in Chicago!


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.


What I use every time I travel:

  • To book hotels:
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     Where is Chicago located


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 existing 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 one of the most beautiful cities in the US again, despite the tragic events I’ve mentioned.


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





TOP 10 things to do in Chicago


     1.Take a selfie at Cloud Gate aka The Bean


Since it’s located right in the heart of downtown, it’s impossible not to spot it. 


The Bean is a neat piece of architecture designed by Anish Kapoor and one of the best things to see in Chicago


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 since it’s one of the top 10 Chicago tourist attractions! For the record, its weight is not less than 100 tons.


Find here the best hotels in Chicago. 





   2. Relax in the Millenium Park | Top 10 things to do in Chicago



Like all of Chicago’s architectural style, this park is truly spectacular, as well.


Home to the Bean, Lurie GardensCrown 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 an enjoyable way to walk around.




     3. Admire the architecture on 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 top 10 Chicago tourist attractions, a place that I’m sure both tourists and locals love it.

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


Book a river cruise on the Chicago River


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







     4. Visit 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 museum 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.



     5. Go Ice skating in Millenium Park | Top 10 things to do in Chicago


     Unfortunately, skating here is only available in the winter season. Personally, I would say that is a big rival of the Central Park rink in Manhattan.


Moreover, here the admission is free. For daily hours of operation, you can check the website. 




     6. Don’t miss Willis Tower and the Sky Deck:


  Willis Tower, previously named Sears Tower, was the tallest building globally for over 25 years

 If you wish to have a unique and, at the same time, a terrifying perspective of the city, 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 four boxes. Also, four 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.









 7. Walk along Michigan Avenue:


 Are you a shopping addict? Then this is heaven for you. Michigan Avenue is Chicago’s most famous 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.

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. 



8. Admire the Water Tower | Top 10 things to do in Chicago


     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.



     9. Stroll the 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 MuseumPier Park, IMAX Theatre, and of course, the Ferris Wheel


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



   10. Stare at Chicago’s amazing 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 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. 


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 to see 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.




     Other places to visit, besides the top 10 Chicago tourist attractions:


  • 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 costly. If you check into a hotel, make sure you’ll find one that already has parking included and instead use the subway.

2. Try to get to the top of Willis Tower at least an hour before the sunset to admire the breathtaking panoramic views.


You must see them in the natural light, but also after it is getting dark, 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 freezing outside and extremely windy.

4. The public transport is perfect 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, such as the Art Institute.




  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



There are many hotels in Chicago, but it is best to stay somewhere close to all tourist attractions.


Even if the subway works very well in the city, nothing compares to living right in the heart of the metropolis. Here are my suggestions for the best hotels in Chicago, suitable for any budget:


  • low budget: Central Loop Hotel– fitness center, private parking, good location
  • mid-range: Kimpton Hotel Monaco Chicago – fitness center, wonderful breakfast, restaurant, bar, great view
  • luxury: The Langham Chicago– swimming pool, amazing location, restaurant

Chicago is located in the center of the United States, which means getting here is very easy, regardless of how you choose to travel.


You can get to Chicago via airline, automobile, rail, and other modes of transportation.

When booking flights to Chicago, you have two options: the big, modern O’Hare International Airport (ORD) and the more affordable Midway International Airport (MDW) (MDW)


Chicago is a relatively safe city, and most tourists will spend their time in the town around The Loop, an area densely packed with public art and institutions.


Pickpockets are the only thing to be concerned about in this area.

When in Chicago, try to avoid shady neighborhoods and take standard precautions.




Although there are so many things to do in Chicago, three days is plenty of time to visit the city’s main attractions.


If you want to extend your visit and add more tourist attractions in Chicago to your itinerary, then 5 to 7 days should be enough.

 Many other blogs can recommend the best restaurants in Chicago. Still, if I were to make a small list of my suggestions, they would be Honey Butter Fried Chicken, Pat’s Pizza and Ristorante, Hermosa Restaurant, and Kasama.  



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