Friday didn’t work, so a Saturday morning flight it was, and that’s how we ended up in the hotel lobby, for the first time, at 7:30am. It was pretty quiet, with some people checking out early, or getting out into the city for breakfasts or whatever. The main desk had two people at it, with a woman off to the side at a separate desk tapping away on a keyboard.

One of the guys called us over and started the expected and appreciated friendly chatter. We got all the what brings you here and have you been before stuff out of the way, with the standard explanation from my wife of how she lived here for a long time and we try to visit when we can, and the conversation settled into a rhythm while he explained how our room wouldn’t be ready for a while, but we could check bags if we wanted.

Now, I should say that I appreciate the art of the up-sell, but wasn’t expecting it in this scenario. I figured weekend in the city with nearly perfect weather probably meant a pretty full house, but - “You have a good view with this room, but I have a room with one of my favorite views in the hotel available, if you’re interested, for only a little more.” I asked if it was really his favorite and he paused to make sure we knew it was honest. Val and I glanced at each other and I said let’s do it.

“You’re gonna love it,” he assured. The woman at the desk with no clear purpose continued typing off to my left. We finished the process, took our bags, and left for some steps and snacks.

There was no stated agenda for this weekend. Val was joining me for a work trip / annual meeting in St. Louis and I had figured if I had to go halfway across the country anyway, we might as well do it together and involve Portillo’s. She didn’t have any problem saying no to that.

I made the conscious effort to tell none of our Chicago friends we were doing it. Sorry, Chicago friends. This was a getaway weekend for us and before I subjected my wife to team dinners and client events, a little unstructured one-on-one time was necessary.

We clocked our first 3 or 4 miles of the day that morning before making it back to the hotel. It was windy but such is Chicago, and mid-70s in the best June way you can get.

We made it back to the lobby and our room wasn’t ready yet. So we sat. They were supposed to send a text message when it was, but we camped out in the lobby on a bench where we had a good view of the goings on. All sorts of people were checking in and out now. We’d had this hotel in our sites for a while because of the rooftop bar. The crowd seemed to justify the decision.

The front desk had added some clerks. Our guy from that morning was still there, charming more people but less upselling since he’d gotten us early, presumably. The lady to the side was still at her computer. I really can’t figure out what she was doing but, the separate desk and unwavering focus - I should have just asked. Two other people had joined to help with the check in/out session. One was entirely professional. The other was clearly coming off something.

There’s a matter of timing when you’re sighing, rubbing your face, or nodding off against the wall that is unbecoming of customer service. This guy had mastered the art of doing it in between guest glances and exchanges. If we weren’t fixated on how out of it he was, I don’t think anybody else would have noticed. A person would pause and go to get something from a purse and he’d do the hardest eye/bridge of nose rub you’d ever seen before looking back up and smiling just in time. It was a masterclass in slack. I may have said he was my idol several times while we waited.

In what barely but still qualified as an early check-in, we eventually got the room keys and headed up to see if the up-sell was worth it. Bags in tow we navigated all the way to an end of a hall that felt a little maze-ish to even find. Front desk man (and not mysterious off to the side desk lady, but who knows, maybe she was involved?!) delivered.

When I say best view I’ve ever had out of a hotel room window in my life - look:

More snacks were required, for World Cup viewing purposes, and based on the already overbooked watch party on the rooftop, we opted for the room. A hotel towel makes an excellent picnic cloth.

Evening strolls were in order, and we were at that point of delirium where you’re just trying to make sure you can get a good night sleep to do it all again tomorrow. It was all successful, so far. And when we navigated back into the room, we were excited to see the city at night in the window, and again, the up-sell did not disappoint.

Serendipity isn’t an accident. My brain keeps going back to what Joe Pine or Shannon Staton said about how you have to program serendipity into things. If you leave enough space, you get moments like this.

As we were marveling at the view I wondered why the river was flashing a not-stop- light/brake-light red. As I looked a little farther to the side, down to where we had clear view of the lake, because the room up-sell was worth the extra, I admitted out loud that I would have paid even more for this, but to please not tell anybody who worked here, especially not the mystery lobby lady.

“Look.”

Chicago, we love you.

ps. Best/most Chicago shirt ever?