Something went wrong on your trip? Here’s why it can be like winning the points lottery

Tell me if this sounds familiar: You sit down on a totally packed plane and find that your inflight entertainment screen isn't working. Or you pay for Wi-Fi, and it cuts out halfway through the flight. Or, perhaps, your seat is dirty beyond what the complimentary wipe can clean. Then, you arrive at your hotel only to have to wait several hours for your reserved room, or you discover there's no hot water when you turn on the tap.

Fear not, my fellow traveler. Although you may have hit some hiccups on your trip, you may have also stumbled into a lose-win situation that will result in some complimentary perks and compensation allowing you to have a travel do-over in style.

Related: Can I get flight delay compensation? These are the ways you qualify

The road warriors at TPG have experienced all of these inconveniences and more. But we've discovered along the way that a slight inconvenience can often turn into a relatively large reward.

Of course, there are some caveats. We're not advising you to report every small thing that goes wrong with your travels — you will not win points for being persnickety. We're also not focusing on weather or mechanical delays and cancellations, as those are governed by a different set of rules.

Here are some real-life examples from the peripatetic staff at TPG and what you can expect if you run into a similar situation. Most importantly, if something does go wrong, remember that a smile goes a long way when you're asking for compensation.

Real-life airline stories from TPG

I'll start with my own story of how an especially dirty seat resulted in a generous compensation from United Airlines.

I boarded a business-class flight from Newark Liberty International Airport (EWR) to Frankfurt Airport (FRA), and I found that my seat was filled with the remains of what must have been a very fun flight for a young child. There were stickers on the armrest, crayons wedged into the seat and coloring pages in the front seat pocket. A flight attendant watched me throw these things away and apologized. I said it was fine and settled into my seat.

However, when meal time came, I realized my tray was, well, small child sticky — like someone spilled juice then ate a bag of cookies, sticky. I asked for a wipe, but didn't complain. That's when the head purser came to me with a very sincere apology, and what I found to be a very generous offer for a minor inconvenience: either 12,500 United MileagePlus points or a $250 flight credit. Since United points are worth about 1.3 cents based on TPG's current valuations and would total $162.50, I went with the cash offer.

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It may have helped that I have 1K status with United, and the fact that I was in the front of the plane (rather than coach) made a dirty seat more of an issue. But I also think that not creating a scene over a sticky situation helped my case.

Here are a few other airline real-life examples from TPGers:

• "On a Paris to New York City flight on American, my 3-year-old's IFE [in-flight entertainment] wasn't working. They couldn't fix it, so I pulled out our iPad and let her play on that. When we got home, AA customer service gave me 10,000 points. (I'll also note that there was a very disgruntled passenger complaining about a minor spill nearby, so that may have been related to the deposit.)" — Caroline English
• "I paid $8 for Wi-Fi on a United flight earlier this year, but wasn't able to connect, so I submitted a refund request after the flight. 10,000 points were deposited into my MileagePlus account within a few days, which I found to be pretty generous. (There was a strong urine smell in my seat, despite my not sitting anywhere near the bathroom. I think my mentioning of that in my refund request contributed to the hefty points deposit.)" — Stephanie Stevens
• "On a short domestic flight in business class (IAD to DEN), I was offered 5,000 miles on a United flight when they didn't have my special vegan meal after I ordered one in advance." — Rachel Craft

Remember that even though airlines are not required by law to give you compensation for long delays or canceled flights, it doesn't hurt to ask. Oftentimes, airlines will give you miles or even trip credits to use for future flights when you face really gnarly travel problems. If you have elite status, you will usually receive better offers.

Just a few other reminders: Late bags get you some extra points or cash with Alaska Airlines and Delta Air Lines. If it takes more than 20 minutes from when your flight arrives at the gate to when your luggage arrives at the baggage claim, you are eligible for compensation.

Real-life hotel experiences from TPG

We at TPG have also had some bumpy experiences at hotels that resulted in some sweet points rewards:

• "This summer, there was some really intense music going late into the night/ early in the morning (as in, thumping music at 3 a.m.) at the InterContinental D.C. at the Wharf that was keeping me and my pup up one night during a staycation. I initially messaged the front desk about it, thinking it was a neighboring room (it was that loud), but was eventually told it was outside the property and they couldn't do anything. Still, they felt bad (and I have Diamond Ambassador status), so they gave me 25,000 IHG One Rewards points." — Christine Gallipeau
• "I got 15,000 Marriott points at Moxy East Village when they woke everyone up for a life-threatening situation and then said never mind, false alarm (at 4 a.m.)." — Sophia Fen
• "The shower in my room had no hot water, and there were no rooms to move me to at the AC Marriott in CLT. I was there for work, so they comped the room, but that wasn't going to benefit me directly, so they also gave me 20,000 Marriott points." — Yemi Kolawole
• "I got 80,000 Marriott points at a hotel in Paris during the Olympics when the air conditioning stopped working." — Chris Nelson
• "Marriott Bonvoy gifted me 10,000 points after an ugly interaction with a rude front desk agent." — Clint Henderson

Related: Quick points: Get compensation when you're walked from a hotel

We've found World of Hyatt is especially good at remedying problems with bonus points as well. Another colleague got compensation for a miscommunication around early check-in.

Again, it never hurts to ask.

Tips for getting compensation for your lackluster hotel and airline experiences

As you can see, our experiences vary, and so does our compensation. But a few variables remain relatively consistent: First, speak up when something is wrong. Also, be respectful to the airline and hotel employees. They're often the ones who determine what you'll receive as a thanks for sticking with them after a trip or stay doesn't go perfectly.

"In many of the situations ... our flight attendants have the authority to issue compensation. This could be in the form of miles or an electronic travel certificate. In some cases, they can also provide complimentary snacks and beverages from United's selection of items available for purchase," a United spokesperson said.

The important takeaway here is that flight attendants are the front-line in dealing with in-air problems, and they have the ability to try and make up for inconveniences during flights.

For both hotels and airlines, follow these tips if something goes wrong:

• Be nice. We can't stress this enough. Since there is no direct money correlation for inconvenience, these types of compensation are solely discretionary.
• Speak up when something is wrong. Flight attendants and front desk personnel aren't mind readers, so you may need to point out the issues.
• Choose your battles. If you report every small hiccup during a flight or stay, you will dilute your actual complaints and likely not be heard the same way.

Related reading:

• Best travel credit cards
• Where to go in 2025: The 29 best places to travel
• 6 real-life strategies you can use when your flight is canceled or delayed
• 8 of the best credit cards for general travel purchases
• 10 ways to get through airport security faster