Whirlwind in the Windy City: How to Spend 24 Hours in Chicago

Approaching Chicago O’Hare as the plane descended through the clouds that July day many summers ago, I awoke from my midday nap to the captain’s message of our imminent arrival, and to the sight of a stunning skyline towering over a vibrant body of water.

As the wind whipped the water into a froth, I gazed at the scenery, still dazed from my nap, confused as to why I could see the sea from the middle of the continental U.S.

And then of course, it struck me: That was no sea. It was a Great Lake.

In retrospect, I felt foolish for having mistaken Lake Michigan for the ocean, but its cerulean depths and the dozens of people who had taken to the water for summertime water sports caught me off guard. I knew the lakes were great, but I did not imagine them to be this vast. It was at that moment that I understood why Chicago residents considered their coastline a “beach”.

Both times I have visited Chi-town have been for specific commitments, so my free time for sightseeing was limited. The first time, I visited on behalf of the Monroe News-Star as a fellowship recipient of the Specialized Reporting Institute for two days of workshops and lectures on how to cover and report stories on mental health issues.

The second visit was for my friend’s bachelorette party, so as you might imagine, that’s still a blur. However both times during these short visits, I still managed to be a tourist and squeeze in some sightseeing, so even if you have fleeting stay in the Windy City, here’s how to make the most of it.

Stay at the Historic Hotel Cass

If you’re looking for affordable and convenient accommodations, check out the Hotel Cass, which has been taken over by the Holiday Inn Express and now goes by the Holiday Inn on Magnificent Mile.

Fares here are reasonable, but most importantly, this hotel is conveniently located close to major attractions (within minutes) and is in a nice part of the city, too. I ended up walking to most places.  Though the rooms are small, I found it to be cozy, clean and comfortable, and I have always loved the character that historic hotels provide, especially in their lobby and staircase areas.

 This 16-story hotel, built in 1925 after the Chicago fire of 1871, once touted itself as a “fireproof building” and “the best little hotel in Chicago.”

Today, only a small placard on its outer front wall indicates this building as the Holiday Inn Express. Otherwise, a much larger sign hanging off of the 5th floor still refers to it by its historic name.

Morning view from Willis Tower

First, wake up early and head to Willis Tower (formerly Sears Tower). Although the tower doesn’t open until 10 a.m. on most days, you’ll want to get your spot in line. Normally, I wouldn’t encourage people to waste time waiting in a queue when they only have a short amount of time in the city, but as long as it’s not overcast or raining, I feel the view is worth the wait. 

Thankfully, when I arrived on a Sunday, I didn’t have to wait too long to get to the viewing deck at Willis Tower, but there was still a decent crowd.

From here, you’ll get complete views of the city and beyond, as one can see four states from the viewing deck (Illinois, Michigan, Wisconsin and Indiana). However, even within the building as you’re weaving through the line, several placards explain the history of its construction and significance to the area.  Previously named after the Sears Roebuck Company, once the largest retailer in the world, this space served as offices for the commercial giant. At 110 floors, this was also once the tallest building in the world, but has now been surpassed by several other financial centers and high-rises globally, including the Burj Khalifa in Dubai, the Ping An Finance Center in Shenzhen, the Taipei Tower and even One World Trade Center in New York City. Still, its construction is formidable, as it took 12,000 workers and three years to build. The views are simply spectacular. 

Brunch at Wildberry

After a morning spent waiting in line and going up to the Skydeck at Willis Tower, you will have worked up an appetite. Head northeast, toward the lake, to the northern edge of Millennium Park for brunch at Wildberry’s Pancakes & Café, and request a seat outside so you can people watch.

This was where my friend’s bachelorette brunch was after a night out on the city, and let me tell you, it hit the spot.

Here, vegetarian savory favorites include the black bean burger, southwestern veggie wrap and garden skillet, but do not miss out on the pancakes! To be honest, I do not remember what specific dish I ordered, but as I almost always do at brunch, I ordered something savory. I swiftly regretted my decision after trying all of my friends’ pancakes and wished I had ordered them instead! 

It was clear this place was a local favorite because the line for brunch extended out of the door, and our group ended up coincidentally running into two other friends who lived in Chicago who happened to be having brunch here as well!

Walk Through Millennium Park

Following brunch, plan to work off your carb-induced coma by walking through Millennium Park to your next destination, the Art Institute of Chicago.

This 25-acre park is where you’ll find the famous “Bean” sculpture, and several other pieces of modern artwork. Millennium Park has come to be a gathering place of sorts.

Located within the Chicago Loop, this park is the site for concerts and festivals, but even when there aren’t any events, it’s certainly worth a stroll. Like many other metros that have transformed abandoned rail lines into beautiful gathering places (Think: Highline in New York City and the Beltline in Atlanta), Chicago converted its forsaken ferrous refuse into an artistic project.

During my first visit to Chicago for the SRI symposium, I walked from Willis Tower directly to Millennium Park in high gear and almost ran straight to “the Bean”,  to capture photos since my phone was dying.

This mesmerizing sculpture, officially called Cloud Gate, looks like one single, smooth piece, but was actually welded together by artist Sir Anish Kapoor out of 168 separate stainless steel pieces.

Little did I know that just a couple of years later, I’d witness more of Kapoor’s fascinating work at the High Museum in Atlanta, and also outside Versailles Palace in France. 

Afternoon at the Art Institute

Just south of Millennium Park is Chicago’s famous Art Institute, one of the oldest art museums in America, and also one of the most notable fine arts schools. Here, you can check out both modern and traditional artwork. Even if you know nothing about fine art, the collections here are so diverse that there is certainly something to speak to every taste. Like the Metropolitan Museum of Art in New York City, collections here span European, American, African artwork and ancient civilizations, as well as modern art and photography. 

After the bachelorette brunch that second time in Chicago, I skipped away from the group for a few hours to meet with Prof. William Handy of Northwestern University’s Medill School of Journalism.

I had met Prof. Handy during my first visit to Chicago during the SRI symposium, and we chatted about the mixing of cultures in the U.S., millennial trends and changes taking place in modern newsrooms. It was such an honor for me because in high school, I had dreamed of going to Northwestern to pursue journalism, but ultimately stayed local in Gainesville to pursue journalism at the University of Florida. I remember that when I told him I’d be going to business school but maintaining a blog to continue writing, he asked me what my blog was about. I couldn’t answer with much precision then, but now, five years later, it feels good to see that I’ve narrowed the focus of this blog more, all because he asked me that question.

Beyond basic art classes and the mention of artists in history lessons during my school days, I don’t know much about art. However, it was both relaxing and invigorating at once to create our own narratives and dialogues to the characters and shapes painted on the canvasses of Seurat, Picasso, Kandinsky and Redon.

When we walked out of the gift shop at the end of our tour, I picked up a postcard image of Grant Wood’s American Gothic, an iconic fixture at the Art Institute, as a souvenir of my visit.

Dinner at a Chicago Style Pizzeria

Before my first visit to Chicago, my dad had told me that trying Chicago style pizza was a must (we’re both foodies), so after wandering through Millennium Park, I found a pizzeria nearby to grab a slice, only to end up ordering a personal deep dish. (You don’t do a single slice of deep dish apparently).

At first, I found it overwhelming and unwieldy:  At the personal pan scale, the dip dish pizza ended up being more like a soup in a bread bowl. Everything about it was thick and falling apart. It was the first time I had to use a fork (spoon?) and knife to eat a pizza, and I didn’t understand why people enjoyed this so much. However, that changed when, a few years ago, I tried Nancy’s Chicago Pizza in Atlanta.

According to their story, Nancy’s Pizza started in Illinois originally as “Guy’s Pizza” by Italian couple Nancy and Rocco Palese, who initially started the business with thin-crust pizzas in 1971. However, they tried different variations until ultimately, they created the stuffed pizza, and that catapulted them into success, allowing them to open Nancy’s Pizza in Harwood Heights a few years later.

The closest location of Nancy’s to the Art Institute seems to be the store at North Broadway Street, and it is a roughly 15-minute car ride. I’d say it’s worth it.

This is hands-down the place I would recommend for deep dish. These stuffed and loaded slices are totally satisfying and worth the calories.

However, if you’re looking for something closer, try Lou Malnati’s on South Slate Street, which is rated highly. I’ve heard that their buttery crust does not disappoint!

Evening Cocktails at A Blues Bar

You’ll need something to wash down that pizza, so grab a cocktail at a blues bar and enjoy some music while you’re at it.

Chicago is known for urban blues, which employs electric guitar and amplified harmonica.  This style of blues focuses more on industrial themes compared to its country blues counterpart. Birthed from the shift of African-Americans from the south to the north in the mid-20th century, musicians would first start by playing casually in the streets and eventually worked their way into parties and night clubs. 

When I visited Chicago as a journalist for the SRI symposium, a group of us decided to go to Blue Chicago after dinner to catch up about the day’s events and to network more. 

The music must have appealed to me because two years later, I joined blues-rock band Maddy’s Ghost as a singer, and the blues pieces were the ones I enjoyed most. What I love about urban blues is that a person could be singing about their troubles but still make you want to get up and dance.

It was a pleasant evening of getting to know my peers better, and I am still connected to several of them on Facebook, seeing links to their news stories and the photos of their travels and life events.

To this day, that trip to Chicago represents to me the last thing I did officially as a journalist. I brought back notes to our newsroom and submitted two more stories to the Monroe News-Star, based on some of the tips and skills I had learned from the SRI workshops. 

My trips may have been a bit of whirlwind, packed with commitments, but I managed to soak up a bit of Chi-town, and it left a lasting impression. Hopefully, in the near future, I will get to explore this mid-western metro at more leisure.