Young Man On The Road #11: And All That Jazz!

Chicago, ILLINOIS 

July 3-6

For the year leading up to this summer, the friends, acquaintances, and Bubba Gump patrons to whom I told about my upcoming adventure often offered advice on places to go.  “Are you going to Boston?”  We sure are!  “You should hit up New Orleans!” I can’t wait!  ”You’re going to New York, right?” Are you kidding?  That’s our number one destination!

A number of people, however, suggested more outdoorsy destinations: Yellowstone, Glacier National Park, the Badlands.  These were all great suggestions, and—as a self-proclaimed outdoorsy type—I seriously considered the options.  However, our goal was to see the countless subcultures of this gigantic country, found in the major cities and college towns across the land.  It was more about the people than the places, and you don’t meet too many locals cooped up in a tent.  So, while I nodded along with sincere interest to the suggestions of campgrounds and hiking trails, a tiny voice in the back of my head kept repeating, “It’s skyscrapers or bust!”

On the third of July, Ian and I descended upon Chicago.

Chicago was our first major city since Seattle, and although we came to dearly love the cities in between, we could not wait to hit up this iconic locale.  It’s the namesake of a band, a musical, and a Frank Sinatra song.  This was big league, baby!

(And you’d better believe I was singing that Sinatra song on the way in. . . )

I knew one person in Chicago.  My college roommate Lawrence attended graduate school at Northwestern, and while he had already moved back to Cali, his friend Connor still lived in town.  I hadn’t talked to Connor since our first and only meeting in SoCal six months prior (which you can read about here:  Young Man Went West #29-B), so I was surprised when he responded to my request for a place to crash.  He had to work during our whole stay, but his cozy studio apartment was right next to Lincoln Park and a short walk to the public rail system (hereafter referred to as “the El”).  Still, Connor played tour guide that first night, showing us how to take the El downtown, taking us to Salsa Night at a bar across from Wrigley Field, and introducing us to his Salsa dancing classmates.

Ian and I had all day to explore the city before catching the Independence Day fireworks show off the Navy Pier.  Good thing Chicago is filled with many requisite destinations, our first being Willis Tower, formerly known as Sears Tower.  Not only was admission to the top of Willis Tower a dollar cheaper than to the top of the Seattle Space Needle, but the tour began with a screening of a very well-made documentary about the history of Chicago and the Tower.  As we made our way through the interactive displays that connected the theater to the elevators, we both declared to like Willis Tower more than the Space Needle. . . and he hadn’t even reached the top!

Continuing in their array of entertaining displays, a monitor in the elevator noted every time we passed the heights of well-known structures around the world.  We finally reach the top and the sliding doors opened up to. . . a gift shop!  Of course.  Still, that desperate capitalistic push did not deter us from the breath-taking sight of city blocks disappearing in the horizon.  There was no outside observation deck, but windows lined the walls the entire way around.  Even more impressive than the endless city was seeing a lake so big that it could fade into infinity.  The largest lake I’d seen before coming to the Midwest was Lake Tahoe, and you can clearly see the other side with a naked eye.

I didn’t spend too much time at the windows, for my main points of interest were the Skyledges.  These all-glass encasements jutted out the side of the building like oversized box windows.   Even the floor—aproximately 10’ x 4’—was completely made of glass.  I couldn’t wait to hop in!  (Actually, by the time I got in, I literally hopped up and down.)

It was in line for the Skyledge that I met a friendly, young couple from Tampa.  We bonded over making fun of the guy ahead in line who fixed his hair before taking a picture of himself in the Skyledge.  Nothing says “instant friendship” like a mutual target of mean-spirited humor.  Whitney and Sam were, of course, curious about our trip and asked many questions, but they also related similar trips they’ve done in the past.  When it was my turn in the box, Sam offered to take my picture.  I would have done the same, but both of their cameras broke right before they got to the top of the Tower.  I offered to wait in line with them again so I could take their picture with my camera and then e-mail it to them later.  They were quite grateful, though it seemed like Sam would have been fine not stepping onto the Skyledge.

Whitney and Sam in the Skyledge

In the gift shop downstairs (of course, there was another one), we ran into Sam and Whitney again and they repaid me by suggesting a must-eat food item: the Italian beef sandwich from Portillo’s.  Ian and I put that on our list, but we had reserved space in our stomaches for a more pressing meal: an original Chicago deep-dish pizza from Pizzeria Uno.

Pizzeria Uno invented the deep-dish pizza in 1943.  The original location is as much of a Chicago landmark as Willis Tower.  The line was long, so we walked to its second location—called Pizzeria Due—just a block away.  No wait for a table, but it took almost an hour for the coveted pie to arrive.  An hour was nothing, I’d had been longing for that succulent pizza since we planned the trip!

That hour gave Ian and me a chance to continue a conversation that started in Madison: basically, my plan after this trip was to go back to Hawaii, save money until December, then move to Seattle.  However, after having traveled through so many intriguingly different cities with the majority of them still ahead, I started to wonder if Seattle should be my next big move.  The point of my living in different cities throughout my twenties was to experience different types of America, to meet other kinds of Americans and learn about their subculture.  Honolulu was definitely an eye-opening first move, but I feel like Seattle won’t be much of a shock.  It exists in the same vein as other West Coast cities I already know and love.  I feel like I’d fit in right away.  What, then, was the point?  We figured I should wait until the end of the trip to decide anything, though I did have my sights set on Boston, and Chicago was great so far.  When our medium deep-dish pizza arrived, my mouth instantaneously switched from talking mode to eating mode and I slipped into gustatory bliss in silence.

I ate half of that pie!

The fireworks show that night was only notable by our cattle-like, hour-long attempt to exit Navy Pier.  The thousands of tourists that gathered on the end of the Pier to watch explosions light up the well-known Chicago skyline got a long lesson in the physics of a funnel as recreated by the fried food stands that lined the path to the main street.  Still, the fireworks show wasn’t a mistake; the skyline was gorgeous.

We crossed off the rest of our “must-see” list on Day Two.  Lincoln Park Zoo?  Check (free admission = awesome).  Italian beef sandwich from Portillo’s?  Check (and thank you, Whitney and Sam!).  Millennium Park?  Check (don’t call the statue “the Bean”; the reality-bending themes behind “Cloud Gate” are really interesting, look it up).  Chicago Dog?  Check (and disgusting!).  We capped off the day with local beer at a bar with Connor.  It was his birthday that day and the least we could do for him was bring him a chocolate eclair cake from Portillo’s and pay for his tab at the bar.  And although we crowded his studio apartment for three days and played keep-away with his house key, I believe Connor did enjoy our company a bit.  At least, I think he did.

Good bye, Chi-town.  I hope you’re as awesome in the winter as you are in the summer; you could be my next home.

"Baby, do you remember when/ Fireworks at Lake Michigan"



Filed under YMOTR Blog

2 responses to “Young Man On The Road #11: And All That Jazz!

  1. Whitney

    So glad that you had such a GREAT time in CHI-Town. 🙂 Even more happy that you made room for Italian Beef’s at Portillos. It was well worth the over-eating — I know, because we went there 3 times during our trip! Be sure to let us know when you make it to Florida — we’ll show you all the local haunts of Tampa and give you a little more to write about on here.

  2. Lydia

    awwww, I’m glad you got both the original Uno’s…well Due’s, it’s all the same, and Portillo’s in!! next time you have to try the Italian Beef at Teddy’s, it’s my favorite, a bit spicier than Portillo’s and actually only has 2 locations=always GREAT quality, sorry I couldn’t share the experience with you! good luck as you venture forth!!

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