Trip Report | Our Son’s 10th Birthday Surprise

Overview

Our son Henry isn’t the type of kid who hands us a long birthday wish list. He’s not super into toys or gadgets. So when his 10th birthday started approaching, my husband Mark and I started thinking less about things and more about experiences. That’s when the idea struck: what if we gave him a 24-hour boys’ trip that he’d never forget?

Enter: a surprise trip to Chicago to see the Lakers take on the Bulls - just the two of them.

At first glance, this might sound like an over-the-top splurge. But the best part? We did it all with points and miles - saving us over $700 and making this unforgettable birthday trip a whole lot sweeter.

Flights: Free, Thanks to Points + Companion Pass

I booked roundtrip Southwest flights using just 12,000 points total, and because Henry flies as Mark’s Southwest companion, his ticket was free (aside from $11.20 in taxes and fees). The cash price for the two tickets would have been $434, but we paid just $22.40.

Accommodations: Hyatt Free Night = Instant Savings

They stayed at the Hyatt Regency Chicago, where a night would have cost $279, but we used a Hyatt free night certificate (thanks to one of our Hyatt credit cards) and paid absolutely nothing.

Before they arrived, I emailed the hotel a couple of hours ahead of time to let them know it was Henry’s birthday celebration trip - and they went above and beyond considering I gave them absolutely no notice (oops). When the guys walked into the room, they were surprised with balloons and a birthday card waiting for Henry. Hyatt really knows how to make moments feel special!

The Trip: Pizza, Basketball, and One Strong 10-Year-Old

Before the game, Mark and Henry grabbed deep dish pizza (as one does in Chicago), and then headed to the United Center for what turned out to be an epic night of basketball.

Much to Henry’s dismay, the Bulls beat the Lakers with a buzzer-beater, and the entire stadium went wild. It was the kind of game fans talk about for years. You can relive the moment here on Youtube (yes, it was all over the news).

Back at the hotel, Henry hit the gym - seriously, who knew 10-year-olds could be so into lifting weights?

Before flying back to Pittsburgh the next morning, they made a quick stop at The Bean for a photo op and one last Chicago memory before wrapping up their quick trip.

Conclusion

This wasn’t just a cool birthday present - it was a reminder of why I started this points and miles journey in the first place. Experiences like this, ones that might normally be out of reach or feel too expensive, become completely doable (and even easy) when you know how to leverage credit card rewards.

We saved over $700 on flights and hotels, but what we really got was something much more valuable: a core memory between father and son.

If you’re new to the world of award travel, check out our free intro guide to learn how to get started. Because whether it’s a birthday trip, family vacation, or spontaneous getaway - you can absolutely travel more, and spend less.

Mark and Henry-approved.