Visiting Chicago

Chicago is a first-rate destination for architecture lovers, with a compact downtown area that’s easy to visit on foot.

I first discovered Chicago in 2003 and immediately fell under its spell. For me, as a lover of urban architecture, it was the ideal place, perhaps second only to New York at the time. Note that the town’s natural setting also contributes to its charm: on the banks of a lake, criss-crossed by a river that allows you to discover it in a different way, it’s a city that’s not only beautiful but also very pleasant. In fact, my comment at the time was “it’s like New York but more peaceful and civilized”.

What’s more, while Chicago is a large, sprawling city, its downtown area – or at least the “visitable” part of it that will interest tourists – is fairly concentrated and easy to get around on foot. What’s more, it’s not an over-exploited city in terms of tourism, and our opinion is that it’s a little too little known and forgotten by tourists. A pity, but it adds to a certain kind of tranquility.

If we were already familiar with the city and didn’t explore it as thoroughly as we would have if it were our first visit, here are the essentials of Chicago to see in a short stay.

You’ll find all the articles about this vacation in the USA at the bottom of the page.

In this article:

A bit of history first

You can’t understand Chicago without looking at its past and some of its founding myths.

First, its nickname of “Second City”. For many, it comes from the fact that Chicago was the second largest city in the USA after New York (before being overtaken by Los Angeles), but that’s not the main reason.

Chicago was totally devastated by fire in 1871, forcing the population to completely rebuild the city. So the Chicago you see today is a second city, rebuilt on the ashes of the first.

Which brings us to the city’s flag, which features 4 red stars framed by two blue stripes, recalling key moments in the city’s history.

The first star represents Fort Dearborn (used then abandoned during the war against the British, then rebuilt and used during the war against the American Indians, destroyed by the Great Fire), the second represents the Great Fire of Chicago, and the third and fourth represent the two World’s Fairs held in Chicago. The two blue stripes recall the two waterways: Lake Michigan and the Chicago River.

The Willis Tower

Like many people, I knew it as the Sears Tower, and at 442 meters high (527m with antennas) it was the world’s tallest tower (24m higher than the old World Trade Center) until the Petronas Towers were built in Kuala Lumpur. But tradition and memory remain, and most locals continue to call it Sears even after its name change in 2009.


So as not to have to wait unnecessarily, we advise you to book tickets in advance for access to the Skydeck, an observation platform located on the 103rd floor at a height of 412m.

Provided the weather cooperates, you’ll have a breathtaking view of the city.


For a different angle, you can also try the 360 Chicago observation deck, located in the former Hancock Center or, to combine the useful with the pleasurable, eat at the building’s panoramic gourmet restaurant, the Signature Room.

The magnificent mile

The Magnificent Mile is a stretch of Michigan Avenue that brings together some of the city’s iconic buildings and a host of mainly luxury businesses.


It’s also here, among the skyscrapers, that you’ll find two highly symbolic buildings: the Water Tower and the Pumping Station.

The Water Tower is a neo-gothic water tower, the second oldest water tower in the United States and one of the few to survive the great fire that ravaged the city in 1871.


Another building to have survived the fire is the Pumping Station, just opposite the Water Tower. This neo-Gothic pumping station is still in use today.


A little more recent, built after the great fire, you’ll find a 1904 fire station in the shape of a medieval castle.


Iconic buildings and the Chicago River

It’s widely believed that Chicago was the site of the first skyscraper. Today, the city has the second highest number of skyscrapers in the United States and the second highest in the world, but that’s not really important: you can build tall towers without them having any architectural interest, and Paris and La Défense are good examples of this.

What’s interesting about those in Chicago is that some of them are of architectural or even historical interest.


There are two ways to appreciate and discover them: walking down the street, of course, but also, and above all, by boat from the Chicago River.


From the lake, the Chicago skyline is superb.


The Art Institute of Chicago

The second largest art museum in the country after New York’s Metropolitan Museum of Art, it houses one of the most important art collections in the United States.

Given its size, it is of course impossible to see everything in one day, so I concentrated on two subjects: the Impressionists and a temporary exhibition on Van Gogh and the painters of the Avant Garde.

Let’s start with the Art Institute of Chicago’s Impressionist collection, the second largest in the world after the Musée d’Orsay in Paris. Simply stunning, there’s more than enough to keep you going for hours.


A must-see if you like this style….and can find your way through the labyrinth that is this museum.

Then the temporary exhibition.


In addition to Van Gogh, it thematically brought together a large number of paintings by artists such as Signac and Seurat.


The exhibition is also enhanced by a superb scenography.

The Museum of Contemporary Art

A museum I’ll mention without going into too much detail.

It’s supposed to have a quality collection, but I didn’t see anything: only temporary exhibitions that I found moderately to my taste. But either I’ve missed something or the main collection isn’t or isn’t easily visible.

A bit disappointed.

The “L”

It can’t really be visited – at best, it can be used – but it’s noticeable and intriguing, with a style that’s a little off the beaten track and will stay with you for part of your visit, whether you use it or pass by it.

What are we talking about? From the typical Chicago metro, the L for “Elevated”.


Even if it’s not aerial all the way, even if it’s just a nickname and not a trademark, everyone now calls it by that name, including its operators.

Unlike New York, the decision was made not to bury the lines over time: Chicago is located on sandy soil, and in this context the costs would be far too high.


No cultural interest, but this pier with its beautiful view of the Skyline is home to an amusement park where you might want to relax.


There’s even a beach nearby.


Bottom line

Far from being a museum city, Chicago can be experienced, visited and appreciated by strolling its streets. There’s what you see and what you feel. What’s more, its town center is on a human scale.

A too little-known destination that we recommend.

The articles about this vacation in the United States

1DiaryPlanning summer vacation 2023 in the USA
2HotelFairfield Inn by Marriott, North Conway (New-Hampshire)
3HotelAC Hotel by Marriott, Portland (Maine)
4FlightParis-Copenhaguen – SAS – SAS plus
5LoungeSAS Gold Lounge Copenhagen
6FlightCopenhagen-Gothenburg – SAS – SAS Plus
7HotelAvalon Hotel – Gothenburg
8RestaurantCarbon, Gothenburg
9LoungeSAS Lounge – Gothenburg
10FlightGothenburg-Copenhagen – SAS – SAS plus
11LoungeAmerican Airlines Admirals Club lounge, Boston Logan
12FlightBoston – Chicago O’Hare – American Airlines – Domestic First
13LoungeEventyr lounge, Copenhagen
14FlightCopenhagen-Chicago – SAS (operated par Hifly) – Business Class
15HotelThe St. Regis, Chicago
16HotelW Chicago Lakeshore
17RestaurantSignature Room at the John Hancock Center, Chicago
18RestaurantThe Purple Pig, Chicago
19RestaurantObelix, Chicago
20RestaurantCabra, Chicago
21RestaurantMiru, Chicago
22DiaryVisiting Chicago
23LoungeAmerican Airlines Flagship Lounge, Chicago O’Hare
24FlightChicago O’Hare – Indianapolis – American Airlines Domestic First
25FlightIndianapolis – Boston – American Airlines Domestic First
26LoungeSAS Lounge – Chicago O’Hare
27FlightChicago O’Hare-Stockholm – SAS – Business Class
28LoungeSAS Gold Lounge, Stockholm
29FlightStockholm-Gothenburg – SAS – SAS Plus
30HotelScandic Rubinen – Gothenburg
31RestaurantProject, Gothenburg
32FlightGothenburg-Copenhagen – SAS – SAS Plus
33FlightCopenhagen-Paris – SAS (Operated by Jet Time) – SAS Plus
34DiaryDebriefing summer vacations in the USA
Today’s itinerary
Bertrand Duperrin
Bertrand Duperrin
Compulsive traveler, present in the French #avgeek community since the late 2000s and passionate about (long) travel since his youth, Bertrand Duperrin co-founded Travel Guys with Olivier Delestre in March 2015.

Trending posts

Recent posts