The (Un) Windy City

By Nomadic Matt | Published August 5th, 2009

Chicago Water FountainIn 1871, most of Chicago burnt down. The summer had been really dry and the city’s wooden houses, built closely together, were a matchbox waiting to be lit. There had been small fires all summer and it was only a matter of time before the city erupted in a major blaze. Around 9 p.m. on Sunday, October 8, a fire began that eventually consumed an area about four miles long, encompassing more than 2,000 acres. It destroyed more than 17,500 buildings, and $222 million in property. Of the 300,000 inhabitants, 90,000 were left homeless.

The traditional account for the origin of the fire is that it was started by a cow kicking over a lantern in the barn owned by Patrick and Catherine O’Leary. Mrs. O’Leary and her cow were quickly vilified but this was more a reflection of anti-immigrant sentiment at the time than any real proof. Eventually, the city absolved Mrs. O’Leary and her cow in the 1990s of any wrong doing.

But out of this tragedy the city was built anew- wider streets, steel and brick buildings, and more green space. Chicago architecture remains some of the best in the world. Beginning in the early 1880s, architectural pioneers of the Chicago School explored steel-frame construction and the use of large areas of plate glass. Chicago had some of the first modern skyscrapers. William LeBaron Jenney’s Home Insurance Building is often considered to be the first to use steel in its structural frame instead of cast iron. Frank Lloyd Wright’s Prairie School influenced both building and furnishing designs. Folks like George Fuller also helped shape architecture and design. Much of Chicago is in this late 19th century/early 20th century American Gothic style that was the definitive style for many buildings across the country.

I was lucky enough to find myself in this architectural wonderland at the end of July for TBEX. While driving across the country in 2006, I also finished my journey here. The city left a lasting impression on me and I was happy to visit again.

While the city is famous for a number of reasons, its biggest draw today is its green space and architectural beauty. There are many green spaces and parks throughout the city- the most famous being Grant and Millennium park, home to the famous Chicago Bean. Chicago has been “greening” itself in hopes of being the country’s most environmentally friendly city. There is even a rooftop garden on top of City Hall. For me, Chicago’s most striking and best feature is its architecture. It has one of the most beautiful skylines in the country. Wide streets lined with American Gothic buildings and modern steel high rises make for stunning visual images and awe inspiring photos.

However, my trip wasn’t solely just spent waxing romantically over the architecture while walking in the parks. With my Chicago Pressbook in hand, I was determined to see as many sites as I could, especially since they were free. I explored the Chicago Aquarium, which also provides excellent views of the city. However, it sadly does not provide excellent information about the fish it features and I found it to be too geared towards kids having a good time and less geared towards providing solid information, especially about the poor state of our oceans. The displays were great and there seemed to be a lot of potential but overall, I was extremely disappointed.

As I museum lover, I made sure to visit quite a few. Though the details of me walking around museums are quite boring, I will nevertheless say the art museum near Millennium Park houses an amazing impressionist wing and I was very impressed with their Monet collection.

My favorite adventure in Chicago was to Navy Pier. Incredibly famous and never having been there before, I was eager to check it out before I left. Navy Pier is sort of like a carnival in a city. It contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, an oddly large number of beer gardens, and even miniature golf. While the place itself is a little campy, with so many things to do there, it seems like it was a good place to walk around on a nice day, have a drink, take the kids, or even take a date.

Chicago’s beauty is everywhere and in everything. Moving at a relaxed and slow pace, even during rush hour, Chicago feels like it is perpetually Saturday. Combined with its beautiful architecture, lots of green space, and delicious food, Chicago is one of my favorite American cities (third behind NYC and Boston) and why no visit will ever get old.

For more information on the United States, visit my country and city guide to US travel.

comments 8 Comments

Stephanie Diehl, aka @traveldesigned

Love your photos of Chicago and from my personal experience in Chicago, you have captured the essence of the city. The aquarium is The Shedd Aquarium and yes, it is lacking in information in the main galleries but they do a nice job with special exhibits.

I like Chicago but the winters are a bit harsh


I love Chicago! I live about 5 and half hours drive away so I go there quite a bit as a weekend trip. I’ve never been to Navy Pier though, should check that out next time. Great post!


Yes it’s gorgeous looking! Have to make a move or travel to this point.Thanks for showing this wonderful place to plan for a vacation. Thanks once again!

Never done Chicago, but it’s on my list. Catch a couple classic Chicago blues shows. I’m heading out to the East coast of Canada soon, heckuva lot closer to Chicago than where I am now. Can’t Wait.

Great Post Matt

Chicago is indeed an architecturally stunning city. I loved the mix of the old and the new.

Chicago is one of my favorite cities. I lived there for several years and it was tons of fun. I haven’t been back in a while so I’m looking forward to a visit there sometime this fall to see some of the new stuff (such as the bean).


I just got back from a weekend in Chicago with my Urban Geography class. Next time you’re there, be sure to check out the Gold Coast, Little Italy (amazing food), the shops in Chinatown (although I’ve never been to a city’s Chinatown before, so this was exciting for me), and Pilsen, a Hispanic neighborhood. Very amazing, good museums, great architecture. The differences in the landscapes of these places is amazing. All within one L ride.

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