Day One in Chicago…it’s all about the Deep Dish

by Jim Bellomo | Sep 27, 2026 | 4 comments

I know, that's what everyone says when they are on vacation but there is something about having a great day that just makes a vacation day special. In fact, so far this has been one great trip.

Kathleen and I had booked my favorite transfer company, Welcome Pickups, to get us to the airport. Our driver kept in contact before we left, and we asked if we could be picked up a little early because the main freeway to the airport was closed for the weekend and we might run into traffic. He was happy to oblige, arrived half an hour early, and then got us to the airport right on time. Our Alaska Air flight was on time (we were kind of worried because it had been more than 90 minutes late the day before), and we were at the gate with plenty of time to spare. Enough time for Kathleen to make a new friend with another woman who had come from check-in via wheelchair…or cool scooter.

One thing that kind of ticked me off (first-world problem coming) was that even though we were flying Alaska in first class, we didn't have access to the first-class lounge. Alaska Air only gives you that if your flight is more than 3,000 miles. Since ours was just under 2,000, we did not qualify. And a beautiful, brand-new Alaska lounge sat just above our heads on the next floor up. Wish we could have seen it.

But no other complaints about the flight. We took off on time, had a nice lunch, arrived early, were off early, had our bags quickly and found our second Welcome Pickups driver of the day, who whisked us into downtown (took about an hour)to our AirBnB, where we found Mike and Cathy waiting for us.

It’s a pretty decent AirBnB. Some folks have told us they have had no luck with vacation rentals, but this is about our 30th, and we have never had a real problem with any of them. This one is excellent. We are on the 23rd floor with an amazing view of downtown Chicago. We are right next to the EL train but being up 23 floors helps. That's the living room up at the top of this page. If you want to see the rest of the photos of the place, check out the AirBnB listing by clicking here.

We have pretty much planned all our eating for this trip… start to finish. We want to try all the foods Chicago is famous for, so last night, after we got in and hooked up with Mike and Cathy, all four of us headed over to Giordano’s (recommended to me by a Trilogy Travel Club member from Chicago) for our first taste of Chicago deep-dish pizza. It was amazing! See the pics below. We ordered two smalls for four of us and could have done with just one. We both ended up taking half a pizza out into the world after dinner. I would like to say I took it back to the AirBnB, but with all the other food experiences we had coming up, it just didn’t make sense. But on the other hand, they were spendy pizzas, so we took them with us.

Just outside the restaurant, I ran into a homeless man who asked if he could maybe have a piece. I handed him the entire box, which had half a pizza in it. He was VERY grateful. Mike took his half back to the building we were staying in for the concierge, who had been letting us in and out. He too was very grateful. We loved the pizza, but there was just too much of it. I also need to mention that when you go, they bake the pie fresh, so it takes 45 minutes from the time your order goes in until you get the pizza. Thankfully, they had some great salads on the menu as well.

After dinner, it was a quick walk back to the Airbnb for a good night's sleep before our first full day in Chicago. More tomorrow. In the meantime, enjoy the pizza pics.

"You better cut the pizza in four pieces because I'm not hungry enough to eat six."  —Yogi Berra

4 Comments

  1. Anonymous

    looks like lots of fun! Your brother looks like you!

    • Jim Bellomo

      My brother wasn’t in the photo. That’s my best buddy Mike. We won’t see my brother until tomorrow.

  2. Anonymous

    Thanks for the memories of deep dish and Chicago! Wishing you a great trip.

  3. bseabob

    It is really good you got it cut in four….wow