The Upcoming Weekend With My Dad In Chicago

Every year, my dad and I go on a father son trip somewhere for the weekend. We go wherever he wants to go. This year we are going to Chicago – I’m heading out in about an hour. In the past, we’ve gone to Las Vegas, Los Angeles, San Francisco, San Diego, Austin, Miami Beach, Las Vegas again, and a few other places.

I think Chicago will be perfect for us. Our goal is just to hang out. This afternoon we are doing the Chicago Architecture Foundation River Cruise, having a drink with my long time friend Jeff Hyman (my very first VC investment was in his company Career Central, which ended up changing it’s name to Cruel World, which was fitting for its ultimate demise), and then dinner at Swift & Sons.

Tomorrow morning I’m going for a long run, we are going to the Cubs game, getting a tour of Wrigley Field, and then having dinner at Coco Pazzo with Troy Henikoff (who runs Techstars Chicago) and his wife Kristin. We are heading home Sunday morning.

Dad Asleep at a Cubs Game with Daniel's Support

There will be a lot of chocolate ice cream. It’s our favorite food and we will have it at least twice each day.

Stan Brad Chocolate Ice Cream

Maybe we’ll have it three times on Saturday if they sell it at Wrigley Field.

My only regret about my father son trip with my dad is that we’ve only been doing it for a decade. I wish we had started 40 years ago. If you are a father and your son is at least ten years old, I strongly encourage you to consider this tradition. If you are a son and you are at least 20 years old, I encourage you to take the initiative and just start doing this with your dad.

  • llonyort

    If you can squeeze in another meal, get a rack of ribs from Twin Anchors. Some of the best in town and only $20….it’s where Sinatra ate ribs.

    • I disagree with the Twin Anchors suggestion. As a lifelong Chicagoan, I can appreciate the iconic nature of TA, but would send them to plenty of rib joints that are significantly better. I eat my way through the city.

      I am headed to the Cubs game Sunday (Mother’s Day and my birthday). Looks like you will get some good weather and let’s hope the Cubbies stay hot! As far as chocolate ice cream, there are some great spots. Margie’s Candies is where the Beatles went way back when. I don’t know if you have a principle that you can’t eat gelato, but Black Dog Gelato has a mean chocolate. Amarino should be somewhere close to the Architectural tour (on north State St). George’s Ice Cream way up in Andersonville is awesome too. Jeni’s Splendid is just south and west of Wrigley on Southport.

      Have a great time.

  • MorganHoward

    I appreciate the call to action at the end of this blog post. I recently brought my 13 year old son with me on a business/pleasure trip and we had a great time. We also don’t hold back on the ice cream!

  • Have fun! Troy has been very helpful in the past as I’ve been building Spikeball. Enjoy Swift and Sons– it’s a block from our office.

  • tgodin

    Don’t forget that Sunday is Mother’s Day!!!

  • I love this. My 12 year old and I are actually staring it this year. I have four sons, so the plan is a one on one trip at 12 and then a trip with all the boys who are 12 and up each year after that. My 12 year old is so excited about it. Great post!

  • file this one under posts i wish i read 20 years ago. hope you and your pop had a great time!

  • Just reached out to my dad to propose the idea. We hangout, but it would be so much more meaningful if we intentionally did so outside of other events like holidays. Thanks for the inspiration!