Kindness Goes a Long Way (Or: How Being Chill Got Me a Suite Upgrade)

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We’ve all seen it: the traveler going full Karen meltdown mode at hotel staff over things completely out of their control. Traveling is unpredictable, but here is my hot take: how you treat front desk staff during a crisis will make or break your trip. I spent years watching travelers blow their tempers over minor delays, but keeping cool on a recent Chicago trip proved that kindness pays off in ways you’d never expect.

Here’s what happened to me:

I flew into O’Hare on a Sunday for a work trip to Chicago. Spent the night at a friend’s house up north, and Monday morning, she dropped me off at my hotel. It was way too early to check in, so I left my luggage with the porter, grabbed a lobby coffee, and walked one block to the office.

My post-work plan was simple: get back to the hotel around 4:30 PM, check in, freshen up, change into something cuter, and head to dinner at 6:00 PM. Instead, post-work drinks by the river with my boss ran long, and I didn’t roll into the lobby until 5:30 PM.

Plot Twist #1: The System Meltdown

The porter brought me my bags and I headed upstairs to the lobby, where there was quite a crowd of folks also trying to check in. It turned out that the computer system was down. When I made it to the counter, the front desk agent looked stressed. She immediately handed me a drink voucher, “The computers are down, but we are working on getting them back up and running ASAP! You can enjoy a drink in the bar while you wait.” 

Now, plenty of people would have lost their minds right then. But the way I see it? Hotel staff have zero control over flight delays, weather, or IT crashes. Yelling at the front desk solves nothing. It just ruins someone else’s day.

So, I smiled, thanked her, and said, “No worries! I actually have dinner plans, so I’ll save this drink for later.” I dragged my bags back down to the porter, trusted it would all work out, and went to dinner wrinkled and un-freshened. My friends wouldn’t judge. 🙂

Plot Twist #2: Dude, Where Are My Bags?

Fast forward to 8:30…. I get back from dinner, tired and very ready for a shower. I could not wait to get into that bed. I found the porter, gave him my ticket, and followed him to the storage room…….which was empty. My bags were NOT in the storage room. Great. But I did not panic yet. The poor porter kid was visibly spiraling on the verge of full panic. I stayed totally chill. They’re in the building, I thought. We’ll find ’em. They can’t just have walked out! 

We walk upstairs to the lobby to find someone to ask. And there my bags are! Right behind the front desk! Huzzah! Everyone could relax (I wasn’t stressed. I knew they would have them somewhere.) and the porter was visibly relieved, poor kid. 

The Payoff

The agent who checked me in was the same woman who had given me the drink voucher before. She thanked me for being so patient about the computer outage and the lost bag scare. I smiled and reassured her. No worries! “Literally not a problem,” I told her. “We’re all victims of technology sometimes.” She seemed grateful for my chill tone and the fact that I was unbothered. 

She clicked around on the computer for a few minutes and then asked me how many keys I needed (just one, thanks). “Alrighty, you’re on the 19th floor. This is the wifi code….” 

Now, I stay at this hotel every time I’m in Chicago. My coworkers always rag on me for picking it because it’s old and the standard rooms are tiny — see the photos below showing a typical guest room and bathroom. (Hey, I’m not doing gymnastics in there; I just need a comfy bed and a conveniently short walk to work!) So getting assigned to the top floor was already an exciting bonus! Maybe I’d have a view this time 🙂

I rode in the slow elevator to floor 19, walked all the way to the end of the hall, to my room at the corner, tapped the key and opened the door.

My jaw dropped.

This hotel only has a handful of suites and oversized King rooms. The front desk agent had bypassed all the standard rooms and handed me the keys to a top-floor oversized King room! I could totally do gymnastics in here if I so chose! Yes, this room is the same size as a ‘normal’ contemporary hotel room, but within the context of my usual room here, it felt MASSIVE. And it came with a really nice robe haha. 

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The Lesson Learned

I have no definitive proof that my being kind led to the upgrade, but I would like to think that because I was so chill and kind to the hotel staff, that they rewarded me.

Travel is unpredictable. Tech fails, luggage gets lost, schedules fall apart. But taking your frustration out on customer service staff is a lose-lose move – the plane is still delayed, the system is still offline, and you just made someone’s shift even harder.  

Next time a travel hiccup strikes, take a breath, flash a real smile, and hand out some grace. Best case scenario? You get surprise-upgraded to a suite. Worst case scenario? You made a stressful day a little easier for another human being. Either way, win-win for everyone!