It's worth trying the $20 Dollar Trick to get a complimentary room upgrade. But perhaps the hotel you’re planning on staying at has a bad $20 Trick track record. If you don’t want to try the $20 Dollar Trick, there are a few things you can do to increase your chances of getting a complimentary Vegas hotel room upgrade: 1. Book your room during slower times of the year, such as in the offseason or during weekdays. 2. Be nice and courteous to the staff. Hotel employees often have the ability to upgrade guests, so if you’re friendly and polite, they may be more likely to help you out. 3. Ask (politely) when you check-in if any complimentary upgrades are available. 4. Be nice! Vegas deals with a lot of people…A smile and polite demeanor often help when trying to get something for free in Vegas. 5. Be sure to tip well. Often, it’s those little extras that make a big difference when it comes to receiving VIP treatment.