How to Make the Most of Six Hours in Chicago

Once I disembarked the train, I had one mission: make the most of six hours in Chicago.

Six hours is all I had because the Amtrak Lakeshore Limited I boarded in Boston just 24 hours earlier rolled into Chicago about 3 hours late. I will admit that I was slightly annoyed at this. I had loosely mapped out a fantastic, full day of exploring the city. This city that I’ve only been able to see while flying in and out of O’Hare International Airport at least a dozen times over the years. I knew I would have to miss out on something on this layover, but what would it be?

As I walked away from Union Station and across the Jackson Boulevard Bridge, I spied the line for Skydeck Chicago wrapping around the Willis Tower. My heart sank. This was on the top of my list, but I knew that it would be what I would be missing. There was no telling how long it would take to get inside. Ain’t nobody got time for that.

It’s ok though. I already knew I would be back someday soon, knowing six hours would not be enough.

I stood on the steps at the Willis Tower, looking around at the crowds and calculated my next move. Yes, I would be back. But first…

Give me some real food. NOW.

Priorities, right?

When I first started planning this trip, I knew I wanted some deep dish pizza. After grazing on dried fruit, trail mix, and Jolly Ranchers for 24 hours I needed something cheesy and hot. More than a handful of people told me to check out Giordano’s. I took that advice and it was deliciously worth the 45 minute wait.

That was a reality check, though. Who has two thumbs and loves thin crust pizza? This girl.

Giordano's in Chicago Deep Dish Pizza

My very own personal deep dish pie from Giordano’s.

While I waited for my personal deep dish, I grabbed a coffee at a nearby coffee shop and spoke to a representative of Big Bus Tours. I was quickly convinced that this would be my opportunity to see as much of the city that I could in my dwindling hours. Big Bus Tours is a hop-on-hop-off, double-decker bus that drives a loop route around the city — take a look at the route map. A new bus can be caught about every 20 minutes, so I ate my pizza (once I finally picked it up) on the grass, in the warm sun, just across the street from the too-long Skydeck line. It was love at first bite, and worth the near hour-long wait.

“Life moves pretty fast. If you don’t stop and look around once in awhile, you could miss it.” – Ferris Bueller


A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. From Wikipedia.

Confession (that I’m not at all embarrassed about): I imagined spending the day in Chicago just like Ferris, Cam, and Sloane did when they ditched school in Ferris Bueller’s Day Off. Minus the baseball game at Wrigley. And now minus staring down at the little ant-people from the top of the Willis Tower. Adding to the list of things from Ferris and company I would not be replicating was touring the Art Institute of Chicago, and having a staring contest with the painting: A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat.

However, I did get to see the two lions, which flank the museum entrance, donning their helmets in support of the Blackhawks. Who, I learned, won some sort of big championship game pretty soon after I left Chicago. I am so not a hockey fan, but that was cool to see.


This was actually the first stop my bus came to after I boarded it, and I ditched it right away because the tour guide was a snore fest. She was so boring, I felt kinda bad for her. She sat in a seat at the front of the upper level of the bus with a microphone in hand, but I could barely make out any of the (architecture?) commentary.

Pretty much all of Millennial Park is an art installation.

This was a perfect spot to hop off because Millennium Park is right across the street. I walked around this area for at least a couple of hours. This park is full of beautiful art installations, like Cloud Gate which creates stunning, but skewed views of the Chicago skyline with buildings varying in architectural styles. Although taking uncrowded photos at Cloud Gate is difficult, the reflections of the Chicago skyline, blue skies, and wispy clouds, and even the people are beautiful. I have to admit, I’m slightly obsessed with this Chicago landmark!

Cloud Gate at AT&T Plaza in Millennium Park, Chicago

Cloud Gate at AT&T Plaza in Millennium Park, Chicago

Also in Millennium Park is the Crown Fountain by an artist named Jaume Plensa, which celebrates its 10th anniversary this year. Portraits of almost 1000 Chicago residents play in a loop across the face of two glass block towers at either end of a reflection pool that stands 50 feet high.

As part of the 10th-anniversary celebration of Crown Fountain, another installation by the same artist has been erected in Chicago. One of four cast iron and resin sculptures, featured in the photo above, is at the Michigan Avenue entrance of Millennium Park. This one, the largest of the four sculptures, is named “Looking Into My Dreams, Awilda.” The additional three smaller sculptures are located at the South Boeing Gallery, which I did not venture to but are also located in Millennial Park.

Crown Fountain, Chicago


The Jay Pritzker Pavilion and BP Bridge are artistic feats featured in this park, too. If I lived in Chicago, the Great Lawn at the Jay Pritzker Pavilion would be my go-to place to spread out a blanket and a picnic feast in anticipation for a concert to start. The delightfully winding BP Bridge connects Maggie Daley Park to Millennium Park and boasts views of Lake Michigan and a climbing wall. Both the pavilion and the bridge are constructed of shiny, curved stainless steel just like Cloud Gate.

Kenny Chesney caused quite the traffic jam.

On the way back to the Willis Tower on a different bus, with a much more engaging and entertaining tour guide, I opted to just go along for the ride all the way back to my starting point. This was partly due to the traffic we were cruising along with at a snail’s pace and partly due to a traffic control officer not allowing the bus to turn at the intersection leading to Soldier Field — where patrons of that night’s Kenny Chesney concert were flooding in both by car and on foot. So we sat at the light for nearly a half hour before deciding to skip that entire portion of the tour which included Soldier Field, Shedd Aquarium, and Adler Planetarium.

We did drive by Grant Park, where President Obama gave his election victory speech in 2008, and where Buckingham Fountain is located. If you’ve ever seen the opening credits to Married with Children, you would recognize this fountain. Other landmarks I viewed from the top of the bus include the Navy Pier, Hard Rock Cafe, the Hancock Tower, The Water Tower, the Wrigley Building, and Chicago Theater.

Big Bus Tour views

So, while I did not get to hold hands with a chain of school children inside the Art Institute, and my red, convertible sports car was replaced by a double-decker bus (please watch Ferris Bueller’s Day Off if you don’t understand these references), I enjoyed my six hours in Chicago. Pizza, free art, and the sunshine. Could I really have asked for more?

Let’s talk numbers.

This is how much money I spent in six hours in Chicago:

  • Pizza $10
  • Coffee $4
  • Big Bus tour $34
  • Locker at the train station $12
  • Total: $60

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  • Reply
    Mona Hines
    July 18, 2015 at 7:25 PM

    So glad to read that you had a great time here in Chicago!

    • Reply
      Brittany Quaglieri
      July 19, 2015 at 7:49 PM

      Mona, next time I’m in town it will be for at least a weekend, and we’ll go get some Giordano’s together!

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