Hamilton is by far the most talked about Broadway show right now, and with good reason. The music is amazing! If you have heard all of the hype and tried to buy tickets, you probably found the same thing I did. They are only available through resellers and they cost an arm and a leg. So when you read the title of this post, I’m sure that some of you were thinking, “Wait, you saw Hamilton? How much did you pay for tickets?”

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Enter American Express. If you are deep into miles, points, and credit cards, you likely have an American Express Platinum Card. They come with a large annual fee, but the benefits the first year outweigh that fee, making your signup bonus basically free. I’ve had some form of the Platinum Card for several years, and currently Chrissy and I have 3 of them (1 personal and 2 business). It’s a card I highly recommend, but you compare it to other travel rewards here.

Pretty regularly, Amex provides their cardholders with early access to tickets for concerts, shows and sporting events. In this case, however, they really outdid themselves. American Express bought out the entire performance of Hamilton and sold the tickets at face value, but only to Platinum and Concierge Cardholders. To get tickets, you had to call in, select a show (they did this for 4 or 5 dates and times that I’m aware of), and make your payment with you Amex Card.

I was traveling home from New York City with my family when I saw the news that tickets were available. We were on Amtrak and I quickly left the car to make my purchase. My wife and I conferred and decided this would make a great birthday present for Ryan, who turned 13 a week before the show. Needless to say, he was super excited when he opened his present. He had been listening to the soundtrack over and over for a couple of months. Cole had a gymnastics meet that weekend, so we enlisted my parents to come watch him and the dogs, and off the three of us went to The Windy City.


Getting There

Teenage hugs from Mom on our way to Chicago for our Hamilton ticket hack.

Our journey started out at DCA. As soon as we got the Hamilton tickets, I booked us flights on Southwest with points. Out of pocket cost was $5.60 per person each way. Chrissy and Ryan left school after lunch and we headed to the airport to catch our flight. Above you can see what happens when you ask a teen to pose for a picture with his Mom.

Walking to the train from the airport on the way to our Hamilton ticket hack.


Southwest flies in to Chicago – Midway, and the best way to get in to the city for the least amount of money is to take the train. We couldn’t get all the way to our hotel on public transit, so we took the train to the closest station, and then took an Uber from there. The trip took about 45 minutes total. 30 on the train, 5 waiting for the Uber, and a 10 minute drive to the Hyatt Centric Magnificent Mile.

The Hotel

Executive suite bedroom at the Hyatt Centric Magnificent Mile.

I used a Diamond Suite Upgrade to go from a regular room to an Executive Suite at the Hyatt. Although it was far from the most extravagant place we have stayed, the room was plenty big enough and nicely decorated. Above is a shot of the bedroom, and below is one end of the unusually long living room.

Executive Suite living room at the Hyatt Centric Magnificent Mile.

Here, Chrissy is enjoying the funky chair in our suite, and Ryan is yet again giving me a great photo smile (can you sense the sarcasm?). The suite had a king size bed in the bedroom and a sleeper sofa in the living room, but the sofa was so long and comfy that we never even made up the bed. Ryan was happy to just sleep on the couch with a blanket and pillow.

Hyatt breakfast at the Hyatt Centric Magnificent Mile.

One of the perks of Diamond Elite status with Hyatt was free breakfast. The Hyatt Magnificent Mile had a pretty wide variety on their buffet. You could also order an omelet as part of the Diamond breakfast. The pasteries were nothing to write home about, but the breakfast sandwich was just what I needed and the yogurt parfait was delicious. Sadly, by the time you read this, my Diamond status will have expired. In fact, Hyatt has completely redone their loyalty program (not for the better) and Diamond status doesn’t even exist anymore.

Exploring Chicago

On Friday evening, I went to a meetup with other miles and points people. Since the Platinum Card is quite valuable in that community, there were a lot of us in town. Richard Kerr set up a Travel Hacking 101 meetup and we had a great time. While I went to that, Chrissy and Ryan wandered around the Magnificent Mile and did some shopping. We found out when packing that Ryan didn’t have a nice shirt or nice pants that fit, so we had to buy him some appropriate clothes to go see the show the next day. He also managed to talk his mother into a new winter jacket and he used his own money to buy a couple of pounds of chocolate at Ghirardelli. They had sundaes and drinking chocolate for dinner. As much fun as I had at my meetup, I’m a bit sad I missed out on that part.

On Saturday, Hamilton wasn’t until 8pm, so we had the whole day to explore Chicago. This was Ryan’s first time in the city and only Chrissy’s second, so we took him to a few of the well known sights around the downtown area.

Dylan's Candy Store on the Chicago Magnificent Mile.

Dylan’s Candy Bar is one place we always try to stop at when we visit New York City. When we saw one in Chicago, we had to pop in and wander around. They have so many different kinds of candy, it’s really quite overwhelming.

The iconic Chicago Theater with ads for Hamilton flying out front.

After getting our candy fix, we walked over to the famous Chicago Theater Marquee. It was not the warmest of days, and of course there was a good wind blowing between the buildings, so we bundled ourselves up as we walked around town. The picture above is a rare moment when Ryan both looked at the camera and smiled for the picture.

Cloud Gate, known as The Bean, in Millennium Park in Chicago.

One of the most recognizable spots in Chicago is Cloud Gate in Millenium Park. Many people know this sculpture simply as The Bean. Whatever you choose to call it, the mirrored surface of this strange shaped giant hunk of metal reflects everything around it. From the skyscrapers to the people laying underneath it, this makes for some pretty fun photo opportunities.

Gazing at the sharks at the Shedd Aquarium before seeing Hamilton in the evening.

Ryan has always loved aquariums. Let’s be honest, Chrissy and I do too, so we spent the afternoon at the Shedd Aquarium. Here Chrissy and Ryan gaze into a tank as a shark swims by. In addition to seeing all of the aquatic animals, we also caught a short 4D movie and a live dolphin show. We ended up spending about 4 1/2 hours there, but if you aren’t quite as obsessed with marine life as our family, you could probably do it in less time.

Comparison of reef life at the Shedd Aquarium in Chicago.

This graph was in my favorite part of the aquarium, a section dedicated to the abundant life on the reefs in the Philippines. This was my favorite because I knew that in just one week, I would be scuba diving on those very same reefs. In fact, as I type this, I am somewhere over the pacific on my way there.

Chicago Deep Dish

Giordano's Deep Dish

You can’t visit Chicago without having some of their world famous deep dish pizza. There are many places to try and everyone has their favorite, but this time we opted for Giordano’s. This was partly because it was one we hadn’t tried yet, and partly because it was three blocks from our hotel. We ordered two personal size pizzas online and picked them up on the way back from the aquarium. Above is a plain cheese and below is pepperoni and bacon. They were as amazing, as expected.



Hamilton Chicago Marquee at the PrivateBank Theatre for our Hamilton ticket hack.

Finally, we got to the moment we had been waiting for. It was time to head over to The PrivateBank Theatre to see Hamilton. When we got there, I had to stop and take a quick picture of the marquee. It was kind of funny how many other people were doing the exact same thing. We had to wait a few minutes for the doors to open. What can I say? We were excited to get there. Then we stopped for a souvenier poster for Ryan and drinks for all of us. The best deal was a soda for $6 that came in a plastic travel mug with a lid and the Hamilton logo. Ryan was kind enough to have a second soda during the second act so he could take a cup home for his brother too.

Our family about to enjoy Hamilton thanks to our Hamilton ticket hack.

Once we had our drinks, we made our way to our seats and found out we had a great view. Don’t we clean up nice? After visiting with some friends who were also at the show, and anxiously awaiting 8:00, the show finally began. Having listened to the soundtrack probably more than 20 times myself, I can honestly say that seeing this show absolutely blew me away. I’ve seen a lot of Broadway shows over the years and this was definitely the best that I have seen. If you have the chance, be sure to go see Hamilton. Who knows, maybe Amex will buy out a few more performances and we will see you there. We are 100% willing to see it again.

Overall, I’d say we had a very successful birthday weekend. The early morning flight home on Sunday was a bit rough, but a nap at home made that all better. If you have been to see Hamilton, let me know in the comments what you thought of the show. I hope you loved it as much as we did.