With a last name like Temperly you would maybe expect he would reflect his name one way or another—and he does. Todd Temperly, the manager of the Waldorf Astoria Chicago is not temperamental; rather, Mr. Temperly, is temperate even in the face of high stress, elevator breakdowns, and New Year’s Eve chaos and New Year’s Day blizzards. With a manager like Mr. Temperly in charge, the Waldorf name lives on as one of high class and caliber.



If you know me, you know that my wallet isn’t high class and caliber. The odds of me landing on an expensive weekend at the Waldorf were rather slim, but once in a while we can find a few gifts rise out of the disaster that is Covid, and one of them is the fact that Hilton extended its free weekend night certificate from 2019. Thus, I found myself with two free night certificates, and a whole, whole lot of points—and the Waldorf in Chicago, still allows redemptions for free standard nights for 95,000 points. For this post, I looked for a random October 2022 night, and there were multiple selections available.

This past winter break, I decided I wanted to spend a couple weeks in my favorite city—Chicago. Chicago is expensive in the summer, but in the winter, hotel rates are down as low as they ever go. The Windy City lives up to its name, and while I suppose some people eschew the cold, I embrace it, so the idea of fleeing balmy Oklahoma, where I lived then, and taking the L, wandering the streets that get dark at 4:30, and freezing my winter boots off sounded downright delightful. With a friend who lives near the OKC airport, I also had free airport parking, so I first cashed in 105,000 Hilton points for the Hampton Inn Downtown West Loop, which somehow earned 4.5 stars on some review sites? I still don’t know how. I added a couple paid nights at the end to make it a full week at the low rate—though I noticed this basic Hampton was running at almost $200 sometimes. Friends, it’s not worth it.

That said, it’s probably easy to see why I was eager to bail on my stay here and book it to Coco’s gingerbread sleigh, famous at the Waldorf.

In fact, I quietly canceled my paid stay at the Hampton Inn, without penalty because I did it early enough in the app, then booked an extra night at the Waldorf by doing two things: First I cashed in a Marriott Free Night Award for the Westin Chicago River North, and upgraded it to a River View room with a few thousand points (see review). Then with the saved money from the DirtyStay Hampton cancellation and the free Westin night, combined that with a hefty Hilton discount I was able to snag, my cost was lower than it ever would be for the Waldorf, so I booked one paid night. And that’s how I landed in front of Coco’s sleigh right there in real life on December 28, to add to my 95,000 points for December 29 and my two free nights redemptions for December 30 and 31.

I had hoped there was a way I could be placed in the same room for my entire stay, of course, but since the extra night had been an add-on, and it was New Year’s Eve weekend, check in was a bit bumpier than I expected—and let’s face it, when you check in at the Waldorf, you expect perfection—even when you know deep down that isn’t realistic.

To be honest, because of the General Manager, Todd Temperly, I hardly recall all the bumps now. But there were bumps and I did not enjoy them. I had to move rooms. In fact, I had pre-selected a room on the 25th floor, which delighted me, since of course I wanted to be as high up as possible in the Waldorf. Also, I really really hate fireworks. I knew hearing them was probably inevitable, but staying on Chicago’s Gold Coast and being 25 floors up was probably the most “controlled” way to minimize the loud sounds. It’s one thing to hear them for a short period of time; it’s quite another to have pops for days and into the night.

However, when I arrived, the front desk agent told me the room I had selected for my other three nights on points was not available for my night that night. After a lot of back and forth—too much for a luxury hotel, I felt, he agreed to upgrade me for the night to a one-bedroom suite from my Deluxe King with Fireplace—but it was on the 11th floor. The view also was, well, not a view. It probably did not help me, a Hilton Gold member, when the man checking in next to me, coasted right in, and the agent helping him said, “Hello, Mr. X. Since you booked through Amex Fine Hotels and Resorts, you have been upgraded to one of our suites with a balcony…” I almost said, sarcastically, “so that’s what it takes to get an upgrade around here. I really was irritated, partly by the opposites tones offered Mr. Fine and myself. My clerk was decidedly not as friendly as the one helping Mr. Fine. And to top it off, I was actually paying for the night in question, and I was an elite member. I think since I was also in my favorite city at one of its best hotels, I was a bit heartbroken.

They offered to let me stay in the upgraded room all four nights. I said I wanted to see it first before making any decisions. I really, really didn’t want to be on the 11th floor when I had pre-selected the 25th. Not in a hotel like that where the view mattered. Shoot, not in Chicago where the view mattered. Sure enough, I got up there, and while it was bigger than some apartments, and quite lovely, the view was depressing and the fireplace was, obviously, in the living room. In a regular room it would be in the only room I was in—which was half the luxury to me. Since the one-bedroom didn’t have a balcony or anything like Mr. Fine’s, it wasn’t exceptionally special enough to warrant me wanting to be more than halfway lower than I was going to be.

I marched back to the elevator to find the clerk and tell him I really wanted to be on the floor I booked—on the 25th floor. And could I not just be there now in the smaller room. I had not been able to book the exact room type when I added on the room, so I understood that part, but I honestly did not consider it an upgrade to move from floor 25 to floor 11—in Chicago! And then he told me there was some problem with room 2505, which I had reserved. If I recall, it was that the people before me had smoked in it, so now it was not going to be ready for me after all! Thanks Smokey Bears! Seriously, who smokes in a room at the Waldorf? But they could move me to 2405, just one floor below, still in a Deluxe King with Fireplace. What could I say? It was the best they could do. It was not the Waldorf’s fault those people had smoked. You can’t make a smokey room un-smokey instantly. UGH! And the only way I could stay in the same room all four nights was to stay on the eleventh floor. I could have an upgraded room type, but I would lose the view. In Chicago, view is everything to me, so I said it was okay and I would move. I was even willing to take a different room as long as it was higher up. Obviously no one there knew that, unlike Mr. Fine, this was, indeed, a luxury stay for me, and not likely to happen again with my incredibly modest salary as an educator. At that point, I had no idea I would even have a new job with a raise on the horizon. This was a dream come true to spend a New Year’s Even weekend on a high floor on Chicago’s Gold Coast. While I was acting like I did this every day, I had never done it before—and knew if I did it again, it probably wouldn’t be for years, so I was feeling a bit like a junior high girl who saw her crush dancing with someone else. On top of it all, with neither room ready at check in time each day, I felt extra frustrated at the time I was wasting simply waiting for rooms. Wasn’t the Waldorf supposed to be seamless.

However, to be honest, it was less about the logistics of everything for me than it was the way it was being handled. I sometimes wonder if it’s my appearance—I am short, and usually in a hoodie and jeans on a cold day in Chicago. And my insecure self with my purple suitcase glanced at Mr. Fine in a suit (probably with a Tumi bag, just in from ORD). I had taken a Lyft from the Westin because it was raining (I would have walked otherwise but it was raining hard, going back and forth between snow). Of course, that comment is my own perception. It could also be that the clerk who helped me was stressed out that day or just plain tired and at the end of shift—or had just arrived and let the house after a fight with a loved one and hadn’t had time to acclimate. We are all human, after all.

But on top of dreaming of my Waldorf stay for months, I’d been on the heels of the bad Hampton stay where I also had a head cold (yes, it was actually a cold) for the first few days, so it wasn’t fun yet (sans the incredible night with the river view in the Westin). I’d been in the city a week, and hadn’t enjoyed my favorite foods, or even visiting a lot of places I wanted to go. Now more time felt wasted.

And then it was “sorry, that room won’t be available after all, and this one may work, but it can’t work until then, and sorry, no room is ready now even though, yes, it’s check in time, we know, and we did tell you check in was now, but it’s not really and…” That awful sentence is what the entire check-in experience felt like. And, probably after watching Mr. Fine’s perfect check in experience next to me, then having to wait to move into the second room, I saw a professional looking man in a suit walk by.

“Are you the manager?” I asked.

That moment changed the entire stay.

It took only a couple words, and Mr. Temperly escorted me to the French café in the lobby, offered me a glass of champagne, (I asked for Diet Coke!) and said he would be right back. Within moments, this class act of a manager had dropped everything else, gotten all the facts straight on the room confusion and situation, sat back down and with professionalism and kindness, apologized for the way it had all gone down. The very first thing he did was comp my room for the first night. I was stunned. Comping a room at the Hampton Inn is one thing, but the Waldorf Astoria on a holiday weekend? Friends, customer service is not dead.

It is important to note that I was not yelling when I stopped him, not demanding that he do something Right. This. Second. I did not announce “I have a travel blog and I am going to write about this horrible mistake,” because 1) My blog is still small anyway, and 2) it wasn’t so much that it was a horrible mistake but more that it was a mass of confusion and I had been looking forward to this stay for months (which I told him when I stopped him). I simply asked him for help straightening it out because it was confusing and I was looking forward to my stay so much.

His response was to offer me champagne, get answers, and comp my room. He obviously could not make a room appear that did not exist. I probably don’t have to explain that the Waldorf was booked for the holiday weekend. But by the time Mr. Temperly was done helping me, I felt like the Queen of the Waldorf, ready to steer Coco’s sleigh.

When I got to my new room—I found a glass display filled with fresh macarons of every flavor from the French bakery downstairs, as well as a personal handwritten card from Mr. Temperly apologizing for the confusion. With the macarons were a number of Diet Cokes–in cans. That is the personal touch that means the world to me. Anyone else likely would have received—and wanted—champagne. If you know me, you know that Diet Coke—especially in cans if there is not a fountain—is the way to my heart. Seeing those sitting on the counter of the mini bar in my new room was like the kiss of customer service that reminded me why I wanted to be at the Waldorf, and why I loved Chicago too.



I turned on the fireplace, looked out the window of the 24th floor into the streets of the Gold Coast of the beautiful city I love, and poured a Diet Coke as I ate a chocolate macaron.

View from the 24th Floor to Chicago’s Gold Coast

Incidentally, it was early in the evening on New Year’s Eve when I encountered Todd Temperly again up close. The Waldorf has two elevators. One had broken, and many people had checked in, on top of those returning back for the evening, before heading out, I am sure. The line to the single elevator was long. At the Waldorf, security protocols dictate one needing a keycard to access the floor number when entering. So Mr. Temperly again dropped everything and manned the elevator for quite some time. I never saw him leave. He ushered people in, in order of the line, asked them their floor, hit the button for them with his master card so they didn’t have to, and then stepped back so the car could go. He did this over and over, in the face of some patrons, obviously, being irritated. Of course, he didn’t break an elevator on NYE, so all he could do was try to streamline the process. There was no easy and direct stair access, but some people still took the stairs to the second floor and then got on, to bypass the line.

The line to the elevator. Mr. Temperly was around the corner managing all of the people with his usual kindness and finesse.

When it was my turn, he looked up at me—it had been days since my check in now, on one of the busiest weekends of the year—this is during Covid and mask protocols too—and said, “Oh, good evening Ms. Tyrrell, How are you? 24?” This man is on top of it. “Yes, please,” I said, “and thank you,” I added, as pointedly as I could—trying to imply a thank you for more than pushing number 24.