Flying into my destination, I woke up to hear the pilot announcing that we were beginning our descent. Outside my window was a beautiful sunrise, the sky streaked with peach and rose hues. There were a carpet of low hanging clouds hugging the ground below us, and knifing through them was the skyline of Chicago.

flying into Chicago.jpg

It couldn’t have been a more perfect first sight of the city, which I hadn’t visited in years.

Just a week or two ago, I hadn’t had any plans to visit, but my mother had called me and mentioned that there was a family reunion there. She assumed that I wouldn’t be able to go, since I was already traveling so much. But… the dates coincided with the only part of the month that I had nothing going on. I leapt at the excuse to visit one of my favorite cities (and also the city where I was born, I might add). I hadn’t had an easy time of getting here, having started with my first-ever train ride last night, from Richmond to Baltimore, followed by sleeping in the airport and boarding a very early flight the next day.

But as we flew over the gorgeous skyline, I knew already that it had been worth it.

After landing in the busy Chicago O’Hare Airport, I followed the signs to the trains going into the city. It was first experience riding the subway, and it went pretty smoothly. The people around me seemed very eager to help, and I felt comfortable asking a woman for some advice about the machines. That’s a real plus about visiting Chicago – everyone is so friendly, even in such a large city.

I got off the train and found myself standing right in the middle of downtown, or Uptown, Chicago, a few steps away from the famous Chicago Theater.

Chicago downtown.jpg

Immediately, I was hit by the frigid cold. My North Face coat now seemed a better investment than ever. Having lived in Miami for the past eight years, I was fascinated by the sight of steam around my face whenever I breathed out. A sign atop a skyscraper read that it was 28 degrees fahrenheit (-2 celsius). Thankfully, however, Chicago’s infamous wind wasn’t all that strong on the day of my arrival.

For the next few hours, I simply wandered aimlessly around Chicago, taking in the city’s grand metropolitan atmosphere.

I couldn’t have been happier. I crossed back and forth over the numerous bridges, recognized some familiar sights, did some people watching, and took plenty of great photos and video footage.

I then decided to go down to the Chicago Riverwalk, which, as you might have guessed, winds along the river within the city. It was much more secluded than the other streets above, which were choked with crowds of people, though there were a handful of people out jogging and walking their dogs.

me at Chicago Riverwalk.jpg

During my last trip to Chicago, back in 2011, I had never gotten around to seeing Lake Michigan, except from a distance. This year, I was determined to go right up to the lake and actually see it in person. I reasoned that following the river would eventually lead to the lake.

Twenty minutes later, I reached the Chicago Harbor, and a marina of sailboats. From there, I found the back entrance to Millennium Park (which I recommend, by the way, since then you get to follow the futuristic twisting metal walkway to the main area of the park).

I spent a bit of time at the Cloud Gate, or, the Bean, which was crowded with people as usual. The ice skating rink was set up below, and I watched the skaters for a bit before continuing on (I contemplated skating, but decided to save it for New York in a few months).

me at Cloud Gate.jpg
me at the Cloud Gate

So far, my aimless wandering had served me well, and led me to three of the four spots in Chicago that I really wanted to see. It was time for the fourth, which I was most excited about – the Skydeck!

The Skydeck is an observation deck on the 103rd floor of the Willis Tower (formerly known as the Sears Tower). It famously contains three glass rooms that are small shelves attached to the side of the skyscraper, allowing you to stand on a floor of glass and look straight down to the street far, far below your feet.park in the city.jpg

view from Willis Tower.jpg
views from the observation deck

I expected to wait in a long line, but it wasn’t so bad – only about 20 minutes later, I was on the observation deck. The sights of the city are, of course, breathtaking. There was a long line to access the glass boxes. You don’t get a box to yourself, you get a part of it – the right side or the left side.

I love heights, and standing in a glass box on the side of the skyscraper was my favorite part of my visit to Chicago.

walking onto the Skydeck.jpg
my first step onto the Skydeck!

After emerging from the Willis Tower, I had intended to head to where I was staying, with my aunt and uncle in Arlington Heights. However, as day turned to night, Chicago took on a particular magic. I couldn’t believe how beautiful the city was, speckled in glowing Christmas lights, with the windows of the skyscrapers illuminated and street lamps casting orange globes over the sidewalks. Every time I took a photo or video footage, I couldn’t believe how gorgeous it looked.

downtown Chicago at night.jpg

I wandered around the night-time city, enchanted, for another hour before heading to Ogilvie Station, as my aunt had directed me. The train to her quaint suburban town of Arlington Heights was only $6, and took a little under an hour.

chicago at twilight.jpg

For the next two days, I saw quite a lot of Arlington Heights – which is one of those cozy little small towns within a city – and had some family time.

I explored the downtown area of Chicago again with my parents, who met in Chicago years ago, got married, and had me. My Dad pointed out some places that he remembered, and I showed them the back entrance to Millennium Park.

Toward the end of our visit, we sat on the steps of a park, looking out at Lake Michigan. Coffee in hand, I didn’t mind the crisp chilly air so much. One of the things that I love about Chicago is that you can be in a park, feeling quite separate from the crazy madness of the pedestrian-choked sidewalks, and have a quiet moment with the magnificent Chicago skyline wrapped all around you.

park in the city.jpg

My trip to Chicago was even better than I had expected it to be – I’m very glad that I was given the chance to visit again!


See My Video About Chicago Here:


See more photos here –

One thought on “Chicago

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s