Flying Back to Chicago: My First Visit in 30 Years

The last time I was in Chicago, Illinois, it was 1993. We piled into a Ram 350 van — the whole family — and took a month-long road trip all the way to New York and back. My brother was born in Chicago. We lived there for several years. And then life moved us to California, and somehow three decades slipped by.

Now we’re finally going back.

Abby has a convention at McCormick Place, which gave us the perfect excuse to book the flights. But if you know me, you know the real reason I’m hyped: I’m a lifelong Bulls fan who has never stood in front of the Michael Jordan statue at the United Center. Never watched a game there. Plenty of Staples Center memories (rest in peace), but not one at the United Center. That changes this trip.

Ontario to Salt Lake City to O’Hare

We flew out of Ontario International Airport (ONT), which is our home base and almost always less chaotic than LAX. Good thing too — the news that morning was all about Delta’s printer situation at LAX causing massive backups. Ontario was calm.

We were about two hours early, which felt right. Checked in, got through security, and let the kid grab some donuts to hold down until Salt Lake City — our layover stop. Our flight was departing on time despite the chaos happening elsewhere.

The Aspire Lounge: Not Worth It

Before boarding we checked out the Aspire Lounge at Ontario. Our membership covers the cardholder and one guest — anyone extra is $50. We went in, looked around, and left mostly unimpressed. The food wasn’t all that, and the space felt average.

Compare that to the Delta Sky Club at LAX before our New York City trip in 2023 — that lounge was genuinely great. The Ontario Aspire just isn’t in the same league. If you’re traveling through ONT and thinking the $50 extra-guest fee is worth it, I’d say save your money unless you’ve got plenty of time to kill.

If you fly Delta regularly, having the right travel credit card makes a real difference for lounge access — the Chase Sapphire Reserve comes with Priority Pass, which gets you into Aspire locations and hundreds of other lounges worldwide.

Layover in Salt Lake City, Utah

Just over an hour from Ontario we touched down at Salt Lake City International Airport (SLC) — a first for me at this airport, though not a first for Utah. We drove through on our way to Denver a few years back and made a detour to Zion National Park, so the desert scenery felt familiar even if the airport didn’t.

SLC is a nice airport. Clean, big, well-signed. We had about an hour and a half before the O’Hare connection, which was plenty of time to walk around and not stress. Meanwhile, the Atlanta Delta flights on the departures board were a mess — CrowdStrike had knocked out a whole swath of their operations. Our Chicago flight was unaffected, but I kept one eye on the board anyway.

Arriving in Chicago

Chicago gave us a welcome-back thunderstorm. We landed about an hour late at O’Hare — not CrowdStrike, just midwest summer weather. It was almost 10:30 p.m. local time when we got in.

We took the ATS train from Terminal 5 to Terminal 2 (the Uber pickup had moved), then met up with my brother Rafy, who picked us up. You might know Rafy from the EV Confessions series — he’s the one with the Kona. Hadn’t seen him in a while, so that alone made the trip feel worth it.

The drive to McCormick Place cut through the city at night. Even from the highway you could tell this was Chicago. The “Chicago Ahead” signs hit different when you haven’t seen them in 30 years.

Hyatt Regency McCormick Place

We pulled up to the Hyatt Regency McCormick Place in the South Loop. Convention hotel vibes — functional, central, directly connected to where Abby needed to be the next morning. Nothing glamorous, but the location is perfect for the week.

The room: two beds, basic, dim. The “view” turned out to be the McCormick Place convention center itself, which I guess counts as a view when the whole reason you’re here is a convention.

It was late, I was tired, and I was hungry. Solution: deep dish pizza.

That’s a welcome-back meal right there. Thirty years is a long time to go without Chicago deep dish — and I’m already thinking about where to go next.

Day one done. Next up: day two downtown and the Rivian Space.