A few weeks ago we took a surprise family trip to see Hamilton Chicago in honor of our son’s 10th birthday. I’m a few weeks late in posting about it. I think I needed a little time to process the fact that it actually happened. We had been keeping this under wraps for about 2 months and when the weekend finally came, I was so worried the experience would not live up to the anticipation. I am relieved to say it could not have gone any better. I’ll share the details with your today.

Making the decision

A few months out from our son’s birthday, I started to think about what we could give him or do for a birthday present. My mind went to birthday presents of the past which sat unused and ignored most of the time. The thought of buying something else to add to that growing list was not appealing at all.

Then I thought, “What is he really into?” The answer was a quick and easy one: Hamilton. We listen to Hamilton all day every day. What if we went to see it in lieu of a big gift or a birthday party? Hmmm…was that even possible? Weren’t tickets all sold out or millions of dollars? I started looking into it.

After calling Brian and seeing if he would knock some sense into me, he agreed that although it would be expensive, it would be a gift not soon forgotten. Turns out Hamilton Chicago tickets cost about 1/3 of what Hamilton New York cost. Plus the boys have never been to Chicago. So Chicago it was. We purchased the Hamilton Chicago tickets and booked the flight.

Setting up the surprise

Two months later, as my son’s birthday approached, I started to get nervous about switching over to an “experiences over things” birthday. Especially because we had not talked it over with the boys at all.

I started to have doubts. Was it selfish on my part because I was so excited about seeing the show too? Would he not count it as a true birthday gift since we were all going and it seemed like a regular family vacation? Had he envisioned getting a Playstation, Xbox or phone or something like that? You just never know. What if he said something bratty or spoiled? How would I react if that happened? If your kids are completely unselfish and unspoiled, this may not have even crossed your mind. They all crossed my mind as a possibility. Nothing like mom guilt to make you think of all the worse case scenarios.

As the day neared, I realized that the surprise would go well if we took some time to make sure it was presented in the right way. We did pick up a few small practical things to not make him suspicious that there was nothing wrapped for him. On that morning, he came to his little pile of inexpensive but useful gifts and we watched him open them one by one. We then handed him an envelope which we asked him to read aloud:

Dear Ben,


When we were trying to decide what to get you for your 10th birthday we really wanted to find something memorable. Something that would make you think back and never forget what a special milestone turning 10 was. It’s a big deal. 


So we were back to our question: What could we get you that would not be soon forgotten? That wouldn’t run out of batteries stop working or get boring after a few days?


There was one thing we knew for sure. Things don’t last. Memories do. It’s the experiences that we’ve enjoyed as a family that have brought us the most joy.


So there was only one thing that we could think of that would make this the best birthday memory EVER for you. And that thing is in the white envelope Dad is holding now. Take a look.


We love you.

Brian Ale and Max

A Hamilton Chicago Birthday Surprise

You should have seen the excitement and anticipation in his eyes as he took the envelope from Brian. Pulling out the tickets, he slowly came to the realization that we were going to get to see something we had told him was impossible. And instead of waiting years for the opportunity for it to come to Florida, we were heading to Hamilton Chicago in three days. He was over the moon. It worked!

3 Days in Chicago

A Hamilton Chicago Birthday Surprise

On the steps of the Field Museum

A Hamilton Chicago Birthday Surprise

Three days later, we were on a plane to Chicago. Although we would only be there a few days, I wanted to make the most of our time in there. Even though I know there are tons of hip neighborhoods in Chicago, we stuck to activities near downtown so nothing could jeopardize getting to the theater quickly.

Speaking of downtown, we stayed at the The Gray Hotel, which is located a block and a half from the Privatebank Theater where the show was playing. I was not going to risk traffic or anything else stopping us from getting to the theater on time. We loved the Kimptons we stayed at on our DC Trip, so we decided to stick with the Kimpton hotel family. Their customer service is top notch. One day they brought Ben a birthday cupcake and some gummy bears. The concierge is also the reason we got to eat dinner next to Alexander Hamilton himself (ok, maybe not the real Alexander Hamilton). More on that later.

A Hamilton Chicago Birthday Surprise

Dreamy shower at The Gray

A Hamilton Chicago Birthday Surprise

A Hamilton Chicago Birthday Surprise

A Hamilton Chicago Birthday Surprise

On our first day, we did the Museums & Parks at Sunset Bike Tour. It was perfect. Bike tours seem to have become a little tradition anytime we are visiting a new city. It’s the best way to see a lot in a couple of hours. Plus, riding bikes is perfect for getting some movement.

On Saturday morning, we went up to the observation deck of Willis Tower and to the Field Museum of Natural History. That evening, we went to Millennium Park which was jam packed. The day we were leaving, we also hit up the Museum of Science and Industry. What an incredible hands-on museum that could have kept us entertained for 6 hours! I highly recommend it if you are going to Chicago any time soon.

A Hamilton Chicago Birthday Surprise

A Hamilton Chicago Birthday Surprise

View from the Willis Tower Skydeck.

As for dining, we played it by ear a lot. Fortunately we did end up at a few good spots that I would recommend if you are staying downtown. The first is Revival Food Hall. Along the same lines as Chelsea Market in Manhattan, the Ferry Building in San Francisco, or Krog Street Market in Atlanta, Revival brings together the best of the best from the local food scene under one roof. We love places like this because we can each grab what we like and meet back at one table to enjoy. The other place we really enjoyed was Cochan Volant. This French bistro style restaurant was on the same block as our hotel and had such a good breakfast that we actually returned two days in a row.

A Hamilton Chicago Birthday Surprise

Revival Food Hall

A Hamilton Chicago Birthday Surprise

Pre-Hamilton breakfast at Cochan Volant

Hamilton Chicago

Okay so enough about all the other stuff. Let’s get down to business. What can I say about this experience? I know the words I use will not capture the surreal feeling of being there. Our front row mezzanine seats were perfect. I love having a direct view of all the action. For this show, believe me, you do not want to miss one movement. The choreography is sublime.

A Hamilton Chicago Birthday Surprise

As the lights went down and the first chords broke through the silence, you could almost feel the electric energy filling the theater. I practically had goosebumps the whole show. The boys sat on the edge of their seats with giant smiles the entire 3-hours. They noticed so many things and wanted to chat about it…a lot. I realized we hadn’t emphasized how important it was to be quiet. Oops. During intermission we discussed it.

Listening to the Hamilton soundtrack has captivated and inspired us for months. Watching the show after listening to it for so long felt like someone had removed a blindfold. And what we saw was even better than we had imagined! We were on cloud 9 with the whole experience.

Because of Hamilton, we visited and experienced the Declaration of Independence, Mount Vernon and the Liberty Bell through new eyes. We have newfound relationships with Founding Fathers that we barely even considered before. I am embarrassed to tell you all the things I was oblivious of about the American Revolution and first government before Hamilton. Believe me, the list is long. And here we were, coming full circle to see the musical that did all of this for us.

After the encore and as people were leaving their seats, a woman from another section approached me. She said she just wanted to let us know how much she enjoyed watching the boys watch the show. I appreciated her saying that, because I loved it too. The joy was exponential on so many levels.

Our seats!


The cherry on top

Just when we thought the highlight of our Hamilton Chicago weekend was over, there was a little extra surprise waiting for us. Since we went to the 2pm show, we got out around 5pm ready to eat. As I mentioned earlier, the concierge at The Gray was awesome. He would text me and ask if we needed help with anything throughout our stay. So after the show, I asked him for a dinner recommendation for a nearby restaurant. He recommended The Dearborn, which was only a couple blocks away and made a reservation for us as we walked.

As soon as we sat down in our cozy booth at The Dearborn, I saw a familiar face at the table next to ours. I told the Brian and the boys I thought it Joseph Morales, the actor who we had just seen playing Alexander Hamilton! Brian doubted it for the whole dinner.

As both of our parties were wrapping up dinner and getting up, I got up my nerve to ask if he had just come from playing Alexander Hamilton in Hamilton in Hamilton. The big smile that followed gave me the answer. It turns out he was also with Remmie Bourgeois, a member of the ensemble cast. They were both so gracious during our short time together. And as we walked away in different directions, we just looked at each other like, “How could this day have been any more magical?!”

A Hamilton Chicago Birthday Surprise

So there you have it. A dream come to fruition in a nutshell. I hope Ben never forgets his special birthday and the memories we created together. I know I certainly won’t.

If you are curious about what Hamilton is all about and how you can see it in Chicago, THIS is a great resource for you.

2 thoughts on “A Hamilton Chicago Birthday Surprise

  1. Claudia

    Wow. That is amazing. I love memory birthdays. We have done this a couple of times. Maybe not to this extent. Your writing is amazing. I felt like I was there with you.

    1. Ale Post author

      Thank you. That is so kind of you to say. We will definitely be doing more experiences like this for special occasions in the future!

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