There are simple things you can do to increase your chances of getting an upgrade on your next flight, hotel stay, or even when you rent a car.
1. Choose Your Frequent Flyer Program Carefully
When picking an airline frequent-flyer program, it can pay to choose an airline that isn't headquartered in your city (there will be fewer elite passengers to compete with for an upgrade).
2. Check-in Later
Check in to your hotel late in the day; you're more likely to get an upgrade if it looks like a better room will otherwise sit empty.
3. Stay at a New Hotel
Stay at a new hotel; staff are more likely to want to woo new guests and spread good word of mouth. You could also think about staying at a large hotel—large hotels with tons of rooms offer a better chance of getting you upgraded.
4. Take Advantage of Online Resources
Priceline.com has a service called Hotel Freebies that shows a range of perks that hotels are offering, including free upgrades.
5. Give a Reason
It helps if you give a hotel a reason to upgrade you. You can tell them that you're there for a special occasion. Also, make sure they know if you are a member of the hotel's loyalty club.
6. Inquire About Partnerships
Let the hotel know if you have any memberships such as AAA or AARP. And, ask if they have other partnerships—they may have some affiliations you might not expect that could work in your favor. Occasionally, hotels partner with airlines in ways that benefit you, too.
7. Just Ask
Surprisingly, sometimes you just have to ask, especially with car rentals. They often have more economy rental reservations than they have vehicles and are eager to hand out upgrades.
8. Write a Note
Before you arrive, write a note to the hotel's manager letting the hotel know how excited you are about your upcoming stay—and why it's important to you. Sharing your enthusiasm about the property via your Twitter and Facebook accounts could help too.
9. Be Nice
It doesn't hurt to be nice when flying. Upgrades can be discretionary, so get the gate agent or flight attendant on your side.
10. Track Award Seats
If you are looking to cash in miles for an upgrade, ExpertFlyer's Flight Alert service will track a given flight for you and let you know when an award seat becomes available. The site's Seat Alert service tracks flights to let you know when better seats become available in your category—an aisle, window, or even a premium seat.