Chicago: United Center, The Bean, and Portillo's

The afternoon took a turn I wasn’t expecting — and I mean that in two very different ways.

I’d spent the morning exploring downtown and the Rivian Space. By the time the afternoon opened up, something even better was on the table: my buddy Eugene, who lives in Chicago, was coming to meet us.

Eugene and I go back to second grade. We did First Communion together at St. Jerome’s. He never left Chicago, and reconnecting with him after decades apart — that alone was worth the trip.

Headed to the United Center

Eugene knew exactly what I needed. We got in the car and headed west on Madison Street toward the United Center.

As a lifelong Bulls fan, I have never been to the United Center. Not once. I’ve watched plenty of games at Staples Center — plenty of losses too — but the United Center? Never. When I was last in Chicago in 1993, they were still playing at Chicago Stadium next door. The United Center didn’t open until 1994.

Just pulling up to the intersection and seeing that building — no game, no crowd, barely any traffic — felt surreal. Staples Center is never quiet. The United Center in the middle of a summer afternoon is just standing there, waiting.

The Banners

We got close enough to see the championship banners through the glass. Six of them. Jordan. Pippen. B.J. Armstrong. The dynasty years that I grew up watching.

I cannot explain what it felt like to actually stand in front of that building and look at those banners. If you’re a Laker fan and you walk into Crypto.com Arena and see the purple-and-gold banners hanging there — that’s how I felt. Except I’d been waiting thirty years for this moment.

Blocked by the DNC

Here’s where it went sideways.

The Jordan statue — the whole reason I came — was completely fenced off. Security everywhere. Turns out the Democratic National Convention was setting up in Chicago that week, and the United Center was one of the venues. They had the entire plaza locked down.

I begged. I told them I was from California. (I don’t think that helped.) I could see the statue through the fence. Just sitting there. Out of reach.

We checked out the Madhouse Team Store and moved on. The statue will be there next time.

Downtown and Millennium Park

Eugene drove us into the Loop. Seeing the skyline from street level — Willis Tower rising straight up, the L tracks overhead, the density of it all — reminded me how different Chicago is from Los Angeles.

We parked and walked through Millennium Park. The cicadas were going. I genuinely thought cicadas were a Southern thing, but Chicago has them too, apparently at full volume in July.

Then we got to the Bean.

Cloud Gate (The Bean)

The full name is Cloud Gate. Nobody calls it that. It’s the Bean, it has always been the Bean, and it always will be.

Walking under it and looking up at the distorted reflection of the Chicago skyline curving above you is genuinely one of the better things I’ve done in a long time. The whole family gathered underneath. I kept thinking about Flight of the Navigator — that 1986 movie with the silver spaceship — because that’s exactly what it looks like.

Just past the Bean, Eugene pointed out Lake Shore Drive and Lake Michigan down at the end of it. He mentioned that when we were kids, our family had an apartment somewhere along North Sheridan Drive, where the backyard was basically Lake Michigan. I lived it — I know exactly how brutal those winters were with the lake right there.

Buckingham Fountain

We walked over to Grant Park and hit Buckingham Fountain as the sun was going down. For anyone who grew up watching Married with Children, you know this fountain — it’s in the opening credits. Standing in front of it in person felt like a memory from a TV show suddenly becoming real.

The lights came on and the fountain put on a full show. The Chicago skyline glowing behind it at dusk was one of the better views of the whole trip.

Portillo’s

Eugene ended the night right: Portillo’s.

Chicago-style hot dogs, Italian beef, burgers, shakes, and the chocolate cake. This is a Chicago institution, and Eugene knew exactly what he was doing taking us there. If you’re ever in the city, don’t skip it.

Day two wrapped up. Didn’t get to touch the Jordan statue, but I got everything else.

Two days later, the convention chartered buses to the Field Museum for a private night event — that’s episode four.