How to Spend a Six Hour Layover in Chicago with Big Bus Tours

Once I disembarked the train, I had one mission: make the most of a six-hour layover in Chicago. All I had was six hours because the Amtrak Lakeshore Limited I boarded in Boston just 24 hours earlier rolled into Chicago about 3 hours late.

I had loosely mapped out a fantastic, full day of exploring the city. So, I was slightly annoyed when we arrived late. I’ve only been able to see Chicago while flying in and out of O’Hare 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 at the top of my list, but I knew that it would be the thing I missed that day. There was no telling how long it would take to get inside, and ain’t nobody got time for that.

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

I stood on the steps of the Willis Tower, looking around at the crowds, and calculated my next move.

How to Spend a Six-Hour Layover in Chicago

First of all… Give me some real food. NOW.

Priorities, right?

When I first started planning this train 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 hot and cheesy. A handful of people told me to check out Giordano’s during my layover in Chicago. So, I took that advice, and it was deliciously worth the 45-minute wait.

As good as it was, though, it made me realize something. Who has two thumbs and loves thin-crust pizza? THIS GIRL.

While I waited for my personal deep dish, I grabbed a coffee at a nearby coffee shop. Then I spoke to a representative of Big Bus Tours. Convinced that this would be my opportunity to cover a lot of ground, I bought a ticket.

About Big Bus Tours Chicago

Big Bus Tours is a hop-on-hop-off double-decker bus with an open top that drives a loop route around the city. The loop takes about 2 hours from start to finish. There are 14 stops around the city at or near attractions like the Hancock Tower, Adler Planetarium, and Willis Tower. Take a look at the route map.

Big Bus Tours starts looping the city at 9 am, and the last loop begins at 5 pm. Between those hours, you can hop on and off the buses as many times as you like. There is a live guide on each bus, but the quality of the commentary will vary. Don’t be afraid to hop off a bus with a boring guide!

After I had bought my ticket, I had to wait 20 minutes for the next bus, so I sat in the sun on a patch of grass to eat my pizza. As I ate, I watched the too-long and too-slow Skydeck line from across the street.

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

Ferris Bueller

Dreams of a Day Off in Chicago

Not at all embarrassing confession: I imagined spending my layover 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 staring down at the little ant-people from the top of the Willis Tower.

Add to the list of things from Ferris and company that I would not replicate is 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 after looking them up, 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 dull, 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 anything that she said.

Enjoy All the Artwork in Millennium Park

The Art Institute stop was a perfect spot to hop off because Millennium Park is right across the street. I walked around this area for at least an hour because pretty much all of Millennium Park is an art installation. It’s full of beautiful art like Cloud Gate (or The Bean), which creates stunning skewed views of the Chicago skyline with buildings varying in architectural styles.

Taking uncrowded photos at Cloud Gate is difficult, but 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!

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 that stand 50 feet high at either end of a reflection pool.

As part of the 10th-anniversary celebration of Crown Fountain, another installation by the same artist was erected in Chicago. One of four cast iron and resin sculptures featured in the photo below 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 Millennium Park.

Other attractions in Millennium Park

The Jay Pritzker Pavilion and BP Pedestrian Bridge are also artistic feats featured in this park. 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 of a concert.

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 a traffic jam.

I opted to hop back on the bus and go along for the ride all the way back to my starting point. This time, we had a much more engaging and entertaining tour guide.

We were cruising along at a snail’s pace because a traffic control officer didn’t allow 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.

Once we were on our way again, we drove by Grant Park, where President Obama gave his election victory speech in 2008. Buckingham Fountain is also located there. 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 the Chicago Theater.

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 red 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?

How Much I Spent During a Six-Hour Layover in Chicago

I spent $60 throughout my six-hour layover in Chicago. Here it is broken down:

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