Chicago – That time I saw Hamilton, twice

This is a “short” tale about riding the thin line between making stupid decisions and taking chances.

Song Recommendation – “Wait For It” Leslie Odom Jr. Original Broadway Cast of Hamilton.


To spoil the anticipation of what happened on leaving New York, I will tell it up front. Due to weather conditions my flight to Buffalo, to see the Niagara Falls, was cancelled. Sorry for the let down, but read on, you won’t guess what happened next :D.

The next flight wasn’t till the following day, and it didn’t arrive till the evening. I took a deep breath and channeled the Uber driver from San Antonio, the “just go with the flow” guy. It was also in that moment that I remembered a piece of advice from a song I’d heard back in the nineties, “don’t go chasing waterfalls . . .” Inspired by my literal interpretation of the song, I decided I would skip the falls and head on straight to Chicago.

You see, I had only planned one full day in Buffalo, so if I was to arrive the next evening I wouldn’t have had any time to actually see the Falls. People before me in the help desk line were having some serious Memphis meltdowns about not being able to get on their cancelled flight. It seemed they believed that if you’re super rude to the flight attendants that they will suddenly un-cancel your flight and that the weather will magically improve. I guess they had places to be, and people to see, and all that jazz.

Anyway, I used my gift of pure charm to get my flight course changed. I had the benefit of no commitments, a calm demeanor and generally just maximum chill ;). It was smooth sailing now, I was going straight to Chicago with no extra charge! Well kind of, the little quirk of my trip was that I had to spend a night in Atlanta, Georgia, and that meant I needed to find accommodation.

In a wild frenzy I jumped on Airbnb and found a place pretty close to the airport. Click, don’t think, confirm. In my defense it was pretty late notice and there weren’t many options.

A few minutes later, I decided I would read a bit more about my accommodation. Only three reviews. . . Okay, interesting. . . Sure, it will be fine. Or so I thought. . .

I soon received an email from the owner saying that someone had claimed to have been robbed outside the house earlier that day, and that I needed to be aware that it was a “gentrifying” neighbourhood. My spidey sense was tingling. Something was fishy.

The investigation continues. . . The three reviews were all recent, and all made by relatively new users. Okay, okay, I guess more experienced users tend to pick properties that have more ratings. I will be fine, it’s fine.

You see, I had to cancel my accommodation in Buffalo, and I thought I wasn’t going to be refunded, so I didn’t want to have to cancel again (even though this one was only like twenty something a night). Yes, I know, another red flag.

I thought my chances of being murdered that night were 40:60. When I entered the house, and the front room was bare (void of furniture), with a creepy abandoned house feel to it, I thought the odds were no longer in my favour. Will this be the room where it happens, I wondered (more sneaky Hamilton references to follow).

I think if there had been plastic sheeting on the floor I would not be typing this post right now. I definitely would’ve thrown away my shot by choosing that accommodation.

I nervously creaked my way down the hall. Why were none of the lights working? (bear with my dramatisation – the lights worked, I just couldn’t find the switch). Instead I used my phone light to guide me. I entered the hallway and approached the door on the right, the one where my room was supposed to be. I inched open the door. Squinting in the darkness I hit at the wall with my hand trying to find the switch. I was helpless.

Wait for it. . .

Then BANG! VOILA! Rays of hope and light shone down from the ceiling, and revealed a neatly made bed with a towel, toothpaste, and a little bottle of water. I was safe! I was alive!

On further inspection of the front room I found furniture piled in the corner, and that paired with a fresh paint smell reassured me that they were probably just renovating. It was actually a great Airbnb!

As a little added twist to my adventure I also had no luggage (lost in NYC, though I got it back the next day).

The next day, in Chicago, I booked a ticket for an improv show at a place called Second City. It was a comedy school where the likes of Tina Fey, Amy Poehler, and Steve Carell started out. It was by far the best improv show I’ve seen. Even though they started out poorly, they went on to blow us all away with perfect timing, funny songs, and hilarious comedic scenes. I was more than satisfied.


While in Chicago I bought a ticket for the Tony award winning musical Hamilton (I just added the bit in italics to make y’all jealous). My seat was four back from the front, in the Orchestra (it was mid-week so it was quite a bit cheaper than usual).

I don’t think any of the original cast are still in the New York show, so I was happy to see the show for a much more reasonable price in Chicago.


The show is about the life of one of the American founding fathers, Alexander Hamilton, and his friend turned foe Aaron Burr, the man who killed him (it’s not a spoiler, the first song/and history tell you it’s going to happen). The musical is a mix of song/rap/hip hop.

The songs are catchy as. . . f’anything. While I was in New York I started listening to the soundtrack, and continued to do so continuously for the next two weeks or so. I feel like it should come with a warning label, it’s that good.

I saw the show, it was amazing. I mean 5 out of 5 amazing! Highlights were Gregory Treco’s portrayal of Aaron Burr, Andrew Call’s hilarious King George III, and Montego Glover as the selfless sister-in-law Angelica. Though the whole cast was awesome. Like, really really good.

On the way home from the theatre it was snowing, which was cool (in bold for those who are not in tune with my pun obsession).

I went home, listened to more of the soundtrack, and hit the sack.

The next day I had a look around the city, I went to the cinema and watched “A Wrinkle in Time”. Guys, FYI – it’s definitely a children’s movie. It was a cool theatre though, with little tables, where you could order food from your seat.

I visited the Sears tower (now the Willis tower), for some great views of the city, and was super extremely tempted to see Hamilton again. I literally had my finger hovering over the buy now button for a second ticket.



I caved the next morning and found a cheap, but a little obstructed view ticket for the Matinee performance. I checked out the “Bean”, had a speed around the art museum, and then settled in for another viewing. This time Alexander Hamilton was played by the brilliant stand-by Jimmie Jetter, who was just as good as the outstanding Miguel Cervantes.

This time I managed to get my playbook signed, and got a few photos, including this bad selfie of me and Gregory Treco (Aaron Burr), and (fangirling) with Jimmie “JJ” Jeter (Alexander Hamilton).

Seriously worth seeing. Lin-manuel Miranda is a brilliant writer.

After seeing Hamilton twice, and checking out the windy city, it was time to depart for St. Louis, a place I was simply visiting because it was a cheaper way of getting to Bozeman (Yellowstone country).

TLDR (too long did not read): I basically made a poor decision that actually worked out well, and I saw the best musical ever, twice.

One thought on “Chicago – That time I saw Hamilton, twice”

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s