The $20 dollar trick, also known as tipping, is a strategy used by hotel guests in hopes of getting a room upgrade or other perks during their stay. It involves discretely slipping a $20 bill to the front desk agent upon check-in and politely asking if any upgrades are available. While it’s not guaranteed to work, it can potentially score you a better room when the hotel isn’t full. So where are you most likely to get some extra value from the $20 trick? Here’s an overview of where it tends to be effective and where it may not make much of a difference.
Where the $20 Trick Often Works
You’re most likely to get results from the $20 trick at mid-range hotels that have multiple room types to upgrade to. High-end luxury hotels typically have standard rates that are quite high, so a $20 tip won’t entice them to upgrade you to a room that costs hundreds more per night. Similarly, budget hotels often don’t have much flexibility with their room inventory. But hotels in the middle tier like Courtyard by Marriott, Hilton Garden Inn, Hyatt Place, etc. frequently have some wiggle room. The front desk agent may be willing to upgrade you from a standard queen to a junior suite or executive floor room for a $20 tip since those rooms don’t have a huge rate variance from the basic rooms.
You also have better chances with the $20 trick when the hotel has low occupancy. If there are lots of empty rooms, the front desk staff has more availability to move you into a nicer option. Slow season and weekdays are ideal times to try it. Of course there’s no way to know for sure how full the hotel will be during your stay, but you can make an educated guess based on the dates and location.
Additionally, independently owned hotels tend to offer more flexibility than big chains. Since they don’t have to follow strict corporate procedures, the staff can easily upgrade you at their discretion. Boutique hotels, mom-and-pop motels, and historical inns are good targets for the $20 trick.
Popular U.S. Cities Where It Works
You’ll frequently get great results from the $20 trick in these U.S. cities:
- Las Vegas – So many mid-range chain hotels compete for tourism that they often have availability to upgrade for a tip.
- New Orleans – Lots of independent and boutique hotels where front desk agents have discretion.
- Atlanta – Major convention city with many large chain hotels that routinely have extra rooms.
- Chicago – Huge hotel market where a $20 trick gets you in the door for an upgrade.
- San Francisco – Not a cheap place to stay, so $20 is appealing for agents to give you a better room.
The $20 trick is also frequently effective in other major tourism destinations like Orlando, San Diego, Washington DC, and Los Angeles.
When the $20 Trick Might Not Work
While it can pay off in many cases, there are also places and situations where the $20 trick is less likely to score you any freebies:
- High-end luxury hotels – A $20 tip is insignificant and won’t get you much.
- Budget hotels – They often have very limited and uniform room options.
- Hotels in small towns – Low room variability and occupancy.
- International hotels – Cultural differences and procedures may make staff unwilling.
- Busy times – Peak seasons and holidays or major local events.
- Conventions – Group bookings may limit room availability.
It’s also key to be polite when asking for an upgrade, not demanding. Rude or drunken behavior is unlikely to be rewarded.
Best Practices for the $20 Trick
To get the most success with the $20 dollar trick, keep these tips in mind:
- Discretely slip the $20 between your ID and credit card when you check-in rather than announcing it.
- Politely ask, “Do you have any complimentary upgrades available?” rather than expecting one.
- Accept if they say no upgrades are available – don’t argue.
- Get the agent’s name and use it when thanking them for considering your request.
- Try it at off-peak times when demand is lower.
Also, don’t attempt the $20 trick at the same hotel chain every visit if you get rejected. Agents may wise up and realize you’re just angling for freebies.
Is the $20 Trick Worth It?
For the minimal investment of a $20 bill, the potential rewards of a room upgrade, waived resort fee, free breakfast, and other perks make it worthwhile to politely try the $20 trick. Even if there’s just a 25% chance it works on any given hotel stay, those are pretty good odds. As long as you ask nicely without expectations, making the attempt is generally smart. Just don’t count on it working every time.
Example Reward Values
Here are some examples of the type of value you might gain from a successful $20 trick:
| Upgrade or Perk | Potential Value |
|---|---|
| Junior suite instead of standard room | $50-$100 per night |
| Executive level floor access | $30-$75 per night |
| Corner room instead of standard | $25-$50 per night |
| Free breakfast | $10-$25 per person per day |
| Waived resort fee | $15-$30 per day |
| Room on a higher floor | $10-$25 per night |
| Late checkout | $20-$50 |
Conclusion
While not a sure bet, discreetly trying the $20 trick at mid-range and independently owned hotels can lead to valuable upgrades and amenities. Know when to make an attempt, ask politely without expectations, and the small investment could bring great returns on your next hotel stay in many destinations. Just don’t overuse it to the point that staff catch on. When used judiciously, the $20 trick is a simple hack to try for enhancing your hotel experience.