EP 1 : A Little World Tour (Chicago Windy City)
Key Takeaways
Chicago is nicknamed the “Windy City” for its cold winds from Lake Michigan. The city deserves 3 to 4 days: Skydeck Willis Tower, Millennium Park, Magnificent Mile, architecture cruise, deep-dish pizza. Calmer and architecturally more beautiful than New York according to many.
Episode 1 – 2 / The USA: Chicago Windy City
What are the most beautiful or well-known cities in the United States? Some will say: New York, San Francisco, Los Angeles, Miami, Las Vegas, Chicago, Why each of them is so dream-worthy or talked about:- New York, for its Statue of Liberty, its skyscrapers, the Empire State Building, Wall Street and many more,
- San Francisco for the Golden Gate Bridge, its originality and Alcatraz prison,
- Los Angeles for Hollywood, its stars and its stars on the Walk of Fame,
- Miami for its beaches and beautiful girls,
- Las Vegas for the casinos, weddings and wedding chapels,
- Chicago for its architecture, its tower, basketball.
During my trip to the USA, I chose to go to Chicago and San Francisco because I have a friend Katie who lives in Chicago, and I wanted to go to California to see San Francisco. I later learned that I had family there.
You should know that I am quite comfortable in the USA because I have already been there twice but this is the first time in these two cities!
I booked my tickets 15 days before leaving with United Airlines because I had previously joined their loyalty program during my last two stays. They have an alliance with companies such as Air Canada, Lufthansa, Swiss Air, etc… so it’s pretty good!
My Experience
I took the Chicago River architecture cruise in 90 minutes: it’s the must-do activity. You understand why Chicago is cited as the most beautiful American city architecturally, ahead of NYC. The ticket costs 50 USD.
I think I did pretty well because I paid 850 euros for the ticket for Paris – Chicago – San Francisco – Portland – Paris (4 flights).
Did you know?
Chicago is the birthplace of the modern skyscraper: the Home Insurance Building (1885) is considered the first skyscraper in the world, with its 10 floors. The city then gave birth to the Chicago School of architecture, which influenced the entire world.
Arriving in Chicago, I am welcomed by Katie and Romain. We go to the station to buy a 3-day Pass, this pass allows you to travel everywhere in Chicago without zone limitation, and it only costs 12 dollars, it’s a bargain for unlimited access for 3 days!
Advantages
- Exceptional architecture
- Vibrant cultural life (blues music, theater)
- Varied cuisine (deep-dish, Chicago-style hot dog)
- Mild summer climate
- Less touristy than NYC
Weak points
- Very cold winters (-15°C)
- Constant wind
- South neighborhoods to avoid
- High hotel costs
- ORD airport far from downtown
We went to Millennium Park located in the Loop area. This park regularly hosts outdoor concerts in the summer at the Jay Pritzker Pavilion. There is also a rather impressive object called “The Bean,” a bean-shaped object that reflects like a mirror! You can have fun making faces and all sorts of gestures! It’s quite nice.
The classic trap to avoid
Don’t buy a ticket for the Skydeck Willis Tower if you can do 360 Chicago (John Hancock Center). Identical view, line three times shorter, similar price (~30 USD). Book online to avoid queues.
- Willis Tower formerly “Sears Tower” named after the company “Sears.” This guided tour includes the projection of the history of this tower, which was the tallest tower in the world from 1974 to 1998, until it was surpassed by the Petronas Towers in Malaysia. The entrance fee costs 15 dollars.
- Have a drink at the top of the John Hancock Tower with a magnificent view of the city at night. One quite impressive thing in Chicago, which differs from big cities, is its incredibly diverse and varied architecture.
- Navy Pier, a pier over a kilometer long on the shores of Lake Michigan. This port was much used for ship embarkations and goods storage, but today it has become a very touristy spot in the city that reflects the appearance of Chicago at the beginning of the twentieth century.
- Walk along Lake Michigan, Lake Michigan separates several states: “Wisconsin,” “Illinois,” and “Indiana.” It is said that on clear days, you can see the other states! It is one of the 5 largest lakes in North America.
In the same vein, the article on Chicago, the opinion of an American woman about her city provides useful insight. Our feedback on South American countries to visit also offers good leads, and the guide dedicated to San Francisco nicely completes the picture.
- See various museums, Chicago has museums such as the Museum of Contemporary Art, the Children’s Museum; I haven’t been there but the brochures make you really want to go.
Find in an upcoming article about Chicago Windy City, «  ;Chicago seen by Katie » If you liked this article, share it on Facebook or Twitter, icon below! “Like” my Facebook page if you enjoyed the visit on my site!
In the same vein, the article on Chicago, the opinion of an American woman about her city provides useful insight. Our feedback on the American continent by also offers good leads, and the guide dedicated to South American countries to visit nicely completes the picture.
How many days in Chicago?
3 to 4 days for the must-sees. 5 days adding museums and neighborhoods (Wicker Park).
Chicago or NYC?
Chicago is calmer, architecturally more beautiful, cheaper. NYC is more iconic. Both complement a US road trip well.
What is the best time to visit?
May to October. Avoid December-March (very cold). Summer (June-August) is ideal for Lake Michigan.
| Site | Duration | Price |
|---|---|---|
| Willis Tower Skydeck | 1h30 | ~30 USD |
| Architecture cruise | 1h30 | ~50 USD |
| Millennium Park | 1h | Free |
| Art Institute of Chicago | 3h | ~28 USD |
| Magnificent Mile | 2h | Free |









