Morning two in Chicago, Illinois. Quick breakfast, then straight into the hunt for the registration area — we were already running late. The Hyatt Regency McCormick Place turned out to be exactly as convenient as advertised: the convention is literally across the street, connected by skybridge. No commute, no Ubers needed for Abby.

Got through registration and found out the big news: Sheryl Crow is this year’s performer. That’s a solid get. They also announced that next year’s convention is heading to Denver — so we’ll probably be in Colorado next summer.
A Window Opens
Abby had presentations to attend. The kids were off at day camp, getting taken around the city by people who actually know Chicago — which, honestly, is better than anything I could have planned on short notice. That left me with about two hours before a lunch commitment and nothing I had to do.
I’d been tipped off about the Rivian Space downtown. It’s about 3.3 miles from McCormick Place, and if you know me at all, that was enough reason to go.

The Rivian Space had just received the Gen 2 vehicles, and I wanted to see them in person. I knew I’d do a full dedicated video on it — and I did — but I wanted to at least get eyes on it before the day filled up.
First Uber Share Ride
I’d never tried Uber Share before. Usually traveling with the family makes it a non-starter. But solo, in an unfamiliar city, with only two hours to spare? Felt like the right moment to try it.
It saved me four dollars. That’s not a life-changing amount of money, but there’s something satisfying about optimizing a random Tuesday in Chicago. I took it downtown.
The Architecture on the Way
One thing I was not prepared for: how different Chicago looks from Los Angeles.

A lot of brick. Real density — buildings right up to the sidewalk, which is just not how Southern California works. It was about 72°F and cloudy with a little drizzle, and I loved every second of it. The weather I grew up with, roughly. I can’t do heat, and Chicago in July was cooperating.
There’s an architectural boat tour available along the Chicago River, and from what I’ve heard it’s one of the best ways to see the city. Didn’t have time on this trip, but it’s on the list for the next one.
Rivian Space
Made it there, got what I came for, and picked up a couple of things: a Gear Guard Gary and a limestone bottle. If you want the full walkthrough of the space and the vehicles, I covered it in a separate post: Rivian Space in Chicago — go check that out.

Back Through Downtown
With a few minutes before I needed to catch my Uber back, I walked around the block.

Spotted a Jeep Gladiator parked on the street — still a great-looking truck, gas and all. Then, a little further down, a Rivian EDV making a delivery. Chicago is clearly already in the mix for those.
Looked up at what I’m pretty sure is the John Hancock Center — now officially called 875 North Michigan Avenue, but nobody calls it that. There’s an observation area up top where the building has an outward lean and it feels like you’re tilting with it. Didn’t have time, but I made a note.
Traffic was starting to build downtown. I called my Uber back before it got worse, made it to lunch, and called the morning a win.
Next up: the United Center, The Bean, and Portillo’s. And if you missed the arrival night, that’s episode one.
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Sherwin Martin
Family man, traveler, and content creator. I explore the world with my wife Abby and our boys — capturing road trips, theme parks, and international adventures along the way.
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