City Breaks, Educational Adventures, Featured, Museums, Road School

Road School Results: Chicago


The answer to my Chicago Guiding Question was answered, in part, by Optimus Prime.

Yeah.  You read that correctly.

In case you didn’t feel like clicking on the link above, allow me to refresh your memory.  My Chicago Guiding Question was:

How important is it to have a planned itinerary when exploring a new city?  Is it better to plot and schedule, or to go with the flow?  Which type of trip is more enjoyable?  Which type of trip is more interesting?

I set out to answer this question by super-planning one day of my visit, and completely not planning the other.  I figured it would be best to plan day one and leave day two up in the air, so that’s what I did.  Here’s how that worked out for me:

Day 1–Planned



The Plan:  Get up early, walk down to the river for an architecture river cruise.  Post cruise, check out Millennium Park–and take photos of ‘The Bean’–on the way to lunch.  Lunch at Max’s for hot dogs or The Berghoff for, well, German food.  Because apparently that’s a thing, at least according to whatever website I consulted in coming up with this plan.  Spend all of the afternoon at the Art Institute before meeting friends at the John Hancock building for drinks.  Continue on with friends to pizza for dinner.  Break at hotel to recharge literal and figurative batteries, additional drinks with additional friend late night.

DSC_0899The Reality:  The getting up part and the river cruise part were great–photo essay blog post to come on that must-do Chicago experience (the cruise, not the getting up early).  But of course, to get to the boat on time, I skipped breakfast.  And by the time the cruise was over, it was 11am.  But I pressed on, following my plan.  Because damnit, that’s what you do when you have a plan.  You press on.

When I arrived at Millennium Park, I found that it was…closed.  Seriously.  They were filming part of Transformers 4, and a huge area of the park was roped off.  So I did what any good travel blogger would do at a time like this–I saddled up to the bar at Park Grill (located conveniently right outside of the park and the closed off area) and had one very, very strong drink for a late breakfast.

Upon rising from my barstool–in the 94 degree sun, radiating off of the concrete–I realized how crucial it was for me to find lunch.  And soon.  Ideally NOW.

So I walked a few blocks to Max’s, a tiny hole in the wall hotdog place that was…closed on Sunday.  I swear to you, I did research.  It seemed like a good option.  Oh well–I had a backup–The Berghoff–and the backup was only a few blocks farther.  In fact, I could see the sign in the distance.  It didn’t seem illuminated, but no matter.  I pressed on.  Because damnit, that’s what you DO when you have a plan.  You press on.

Of course The Berghoff was also closed on Sundays.  At this point I’m becoming fairly confident that everything west of Michigan Ave is closed on Sundays.

I’ve now been semi-drunkenly trudging through the heat for a good half hour.  Mind you, I’ve only had one drink.  But it was a strong drink, it was nearing 100 degrees, and I had consumed zero solid calories all day.  So I leaned up against a support beam for the El tracks, pulled out my phone, and consulted Yelp.

Very near where I gave up, exhausted and starving.  But I took a few photos there, too.

Very near where I gave up, exhausted and starving. But I took a few photos there, too.

Yelp took me four blocks south, to a sandwich place that, upon arrival, I discovered was less ‘a sandwich place’ and more ‘the cafeteria of a hostel’.  Travel tip: maybe don’t consult Yelp in a town run by 24 year old hipsters.  Just saying.

I eventually ended up at yet another Yelp-suggested establishment–a block north of the Art Institute  and right on Michigan Avenue.  It was flashy, it served sub par food, and I was charged $16 for a glass of house Chardonnay.  (When the bill came, I asked the bar tender what the hell.  And he was like that’s the only Chardonnay we have.  And I was like ok, well just so you know, when someone asks for house Chardonnay, they are asking for a cheap glass of wine.  This is not ok.  Here’s your 30% tip, and I will never, never come back here nor will I tell anyone to come here, either.  Travel tip:  do not dine at The Gage.)

As you can see, very little about my planned day went as planned.  Because this is getting long and tedious, I’ll summarize the rest of the day in bullet-list form:

  • The Art Institute was amazing, but my friends wanted to meet for drinks far sooner than I’d planned; I rushed out.
  • My phone died. My external battery died.  I was left phone-less and had to resort to using–gasp–a paper map!
  • Chicago pizza takes a long time to cook.  Fortunately I was with good friends.
  • Second friend got off of work late and I ended up sitting alone at a bar and being sneered at by smarmy business men for a good half hour before he arrived.  But then he arrived and all was well.  And there was gin and laughter and the day ended well.

My planned day in Chicago was not a bad day; in fact, it was a really, really great day.  But nothing–absolutely nothing–went as planned.  Which begs the question–why plan?

Day 2–Unplanned



The Plan:  There wasn’t one.

The Reality: I got a taxi at my hotel and took it to the museum campus–housing the Field Museum, Shedd Aquarium, and the Adler Planetarium.  I had a Chicago CityPASS and  gosh darn it, I planned to use it.  The taxi driver chatted with me as we drove downtown–he asked how I liked Chicago.  I told him it was a great city, and that it was beautiful.  He said: it is more than beautiful, and it is more than great–it is the best city.  My heart grew three sizes.

My plan was to hit the Field Museum first and then make my way to the aquarium (I loves me some fishes); yet when I arrived, I changed my mind.  I decided instead to take a little walk around campus.  And then I found a hot dog stand.  It was ten in the morning, but it was open.  So I bought a hot dog for breakfast.  From a street vendor.  Which is not something I’ve ever done or would ever plan to do.  And I walked around at ate it.

I do not walk around and eat street food.  I just don’t.  Yet that is what I did.  And do you know what?  That was one great hot dog.  And do you know what else?  I felt much better having eaten something for breakfast–even processed meat. (Especially processed meat?)

On board the water taxi, overlooking the Planetarium.

On board the water taxi, overlooking the Planetarium.

My hot dog wanderings brought me closer to the aquarium than to the Field Museum, so I decided to start there.  You know, spontaneously.  After spending a perfectly lovely two and a half hours at the aquarium (detailed post coming soon), I left–only to find a blocks-long line to get in.  Apparently most people started at the Field Museum.  You know, like I had sort-of planned to do.  But then changed my mind.  Behold, the power of spontaneity.

There was no line at the Field Museum.

At some point during the day, I noticed what appeared to be some sort of ferry leaving from a dock nearby; I think I glanced out the window at the aquarium and noticed a line and a little ticket stand.  So I did some quick iPhone Google research and discovered that yes, in fact, there’s a water taxi that leaves from the museum campus and goes directly to Navy Pier.  How fabulously convenient, given that I’d not yet visited Navy Pier.  I mean, I wasn’t planning on visiting Navy Pier, but then I wasn’t planning on doing anything.


So I took the water taxi to Navy Pier.  And when I arrived, it was around happy hour time.  And I thought: I’m feeling pretty happy; I need an hour.  So I had a drink at the nearest bar–in the cool, cool air conditioning (did I mention it was in the mid 90s the whole time I was there?) before wandering around and taking photos for a while.  It was lovely.  And entirely unplanned.

My day ended with a likely too-short taxi ride back to the general vicinity of my hotel, a super-unhealthy (but absolutely fabulous) dinner at Portillo’s (I still think about that Italian beef sandwich.  Like daily…) and an early night in (I tried to blame the fact that it was Monday–that’s why I didn’t go out that night.  But really, it was my overly-comfortable bed at The Hotel Felix.  Detailed blog post on THAT coming soon as well.  But oh…the bed…)

 The Answer

The universe–and, yes, in some small way, Optimus Prime–answered my question loudly and clearly.  I planned, and the gods laughed.  I didn’t plan and, well, I laughed.  Free from the burden to ‘press on’, I had a perfectly lovely–and productive–unplanned day in what is now one of my new favorite cities.  I can’t wait to not-plan my next trip.

Acknowledgements:  (Yes, I’m including an acknowledgement section in a blog post.  Because it’s my blog and I can do that.) I’d like to thank the three amazing friends who met me for various forms of alcohol and carbs during my brief solo visit to Chicago.  It’s a beautiful city, but you are all more beautiful, and visiting with each of you was truly the highlight of my trip.  Here’s to pizza and laughter!  (I’m raising an actual glass.)

Disclosure: Thank you to Hotel Felix for hosting me and thank you to the people at Chicago CityPASS for providing me with a pass to use to explore all that Chicago has to offer.  Of course, all thoughts and opinions are, as always, my own.  Stay tuned for more on my visit to  the windy city, the white city, the wonderful city of Chicago.

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