Favorite Things About Visiting Chicago for First Time + Photos

  • I visited Chicago for the first time, and there was a lot to love about the Windy City.
  • The city felt bigger than I expected, and I found the art and architecture all around fascinating.
  • I was introduced to great new foods, and I had no idea there were so many neighborhoods to explore.

As a Californian, I knew Chicago was an international metropolis. But I was pretty blown away by the Windy City throughout my first visit.

Read on for the things that surprised me most.

My first impression was that Chicago really felt like a huge city

molly at the sears tower in chicago

 

It definitely felt bigger than LA.

Molly O’Brien

Before my visit, I associated Chicago with architecture, railroad history, baseball, Lake Michigan, and, of course, pizza.

But I wasn’t expecting it to feel like such a huge city.

In LA, the buildings are on the newer side because the area didn’t really become a populated destination until the 1900s. Chicago’s population and skyline, on the other hand, have been growing since the 1830s.

My first impression of the city was at O’Hare airport. It was clear how enormous the hub was when it took our plane more than 20 minutes to taxi to our gate after landing.

Then in the car on the way to the hotel I thought, “Holy moly, this city skyline is the biggest I’ve ever seen.”

It’s nothing like New York or San Francisco, which are geographically constricted, or Los Angeles where there’s technically a downtown neighborhood but the city itself is so sprawling.

I knew Chicago was known for its architecture, but there were so many layers to the history

portion of the chicago skyline from the river at sunset

 

The views across the city were stunning.

Molly O’Brien

Architects are like celebrities in Chicago. My mouth was literally hanging open at the beauty of the buildings that surrounded me.

To really soak in the culture, I went to the Chicago Architecture Museum to learn more about the city’s skyline. Then, I went to the Chicago History Museum to learn how much of this city was rebuilt after the Great Chicago Fire in 1871. Finally, I went on an architecture-focused tour on the Chicago River, where I gained a “new perspective” on these towering buildings from the water.

No buildings in Los Angeles come close in height to Chicago’s Willis Tower (formerly known as Sears Tower). The 108-story building is the third-tallest in North America.

molly on the sky deck at the sears tower in chicago

 

The Sky Deck isn’t for the faint of heart.

Molly O’Brien

If you’re not afraid of heights, be sure to check out the “Skydeck” experience and “The Ledge,” where you can hover over the city at 1,353 feet.

Go as soon as it opens up at 9 a.m. because the lines can get long on weekends.

The 77 neighborhoods in Chicago offer a diverse expanse of culture to explore

map of chicago's 77 neighborhoods

 

I had no idea there were so many different communities.

Molly O’Brien

If you’re trying to get around a single neighborhood in Chicago, the city is pretty walkable. Otherwise, there’s a train system that can take you to pretty much wherever you need to go.

Even though I was visiting from LA, which is very diverse, I was enthralled with the different sites and scenery within Chicago’s 77 distinct neighborhoods — each boasting its own impressive history and background.

Our hotel was located on the border of the Loop district within the New Eastside community.

I had no idea Chicago’s flag had so much symbolism

I’ve never been to a city where people are as passionate about their flag. I didn’t even know what LA’s flag looked like before I sat down to write this.

Chicago’s design has an impressive amount of historical significance. The three white stripes represent the North, West, and South sides. The top blue stripe represents Lake Michigan and the north branch of the Chicago River. The bottom blue stripe represents the south branch of the river and the Chicago Sanitary and Ship Canal.

The four six-pointed red stars represent major historical events: Fort Dearborn (the origin of the modern city), the Great Chicago Fire of 1871, the World’s Columbian Exposition of 1893, and the Century of Progress Exposition of 1933–34.

Deep-dish pizza is worth the hype, but there are so many other Chicago delicacies

chicago deep dish pizza

 

I was excited to try the classic dish.

Molly O’Brien

You simply can’t go to Chicago without eating deep-dish pizza.

I went to Lou Malnati’s Pizzeria, where each pie is handmade. There are multiple locations, so you can’t miss it.

I ordered “The Lou” deep-dish style, and it was heavenly. My taste buds were seriously singing as I took my first bite.

They definitely don’t make pizza like this in Los Angeles.

italian beef and a hot dog from portillos in chicago

 

The inside of the restaurant had some wild decorations.

Molly O’Brien

There’s also Portillo’s, which serves authentic Chicago-style hot dogs (no ketchup allowed) and Italian-beef sandwiches.

For something sweet, head to Garrett Popcorn. The sugary smells drifting from the shop can lure people from streets away.

But if you’re looking for something fresher, I was impressed by a trendy convenience store-type shop called Foxtrot. It sold tasty goodies like premade salads, sushi, and warm bowls and also crafted espresso drinks and smoothies on-site.

You can’t go anywhere without running into famous artworks 

shot of the "bean" or the cloudgate statue in chicago

 

There was art all over the parks and museums.

Molly O’Brien

It’s not just the buildings in Chicago that are well-designed and nice to look at. There are impressive indoor and outdoor art scenes here.

Perhaps the most famous destination to check out is the Art Institute of Chicago, which is an absolute can’t-miss for art lovers.

Famous works like “A Sunday on La Grande Jatte,” have been featured in movies like “Ferris Bueller’s Day Off.” The museum also houses classics, like “American Gothic,” and rotating contemporary exhibits.

The Bean — or Cloud Gate, as it’s more formally titled — is a famous work of urban art.

Luckily, it’s very close to the Art Institute for those who are interested in saving a trip. Plus, it’s totally free to visit and take pictures, just head over to Millennium Park.

Though I thought the Bean was cool, I can see how some might find it underwhelming if their expectations are too high. But it was much larger than I expected, and the way it reflects the city skyline on a clear blue day is beautiful.

I definitely needed more than 3 days to explore the whole Midwestern city

molly sitting on a slice of chicago style deep dish pizza

 

There was so much to do and see.

Molly O’Brien

I was only in Chicago for three days, and I had the chance to do and see a lot. But there was still so much left to explore.

It’s the kind of city where you can always find something new each time you visit.

I only really explored the Loop area, where many of the city’s famous attractions are, but I was grateful that it made my trip so walkable, which is nothing like where I live in Los Angeles.

Overall, I can’t wait to get back and see different parts of the city.

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