I have updated this post and have it featured on my new blog SAVING UP FOR DISNEY.
Back when I was a girl (long before the internet, of course) my dad would occasionally receive a newsprint mailer that had national contests. I was intringued by the thought of possibly winning a vacation, cash, even a car. I recall a few times, filling out postcards with the contest addresses as per the instructions and sending them off in the mail, fingers crossed. I never won anything, of course.
When I was in high school my dad won a contest in the newspaper to name a casino in Las Vegas. He was one of many who chose the name ("Excalibur") and was awarded a weekend stay at the new hotel and my mom and he got all their meals for free. That was fun!
I've been pretty lucky through the years, winning a savings bond at my school's grad night party, had my name pulled from the barrel of thousands at the mall when Wheel of Fortune did a casting call (I made it on the show!) and most recently won a $50 Macy's gift card, San Diego Safari Park tickets and an overnight weekend at the Disneyland Resort complete with 2-day park tickets for all four of us.
Us, on the recent Disney trip that I won!
My motto: Someone has to win, why not me?
You know, you can't win if you don't play. I am by no means a professional at this and there are many websites that will go into more detail but this is how I do it:
At least once a week, I do an internet search for contests that sound interesting to me and load the links into an email that I send to myself. There are websites that list tons of contests in a directory like Sweepstakes Advantage and About.com These are the two I use most. I like to look for specific contests too, like travel to Walt Disney World, and I find Disney-themed contest on Mousesavers.
I don't really enter contests with prizes I don't want or need.
I do "like" certain companies on Facebook that run frequent promotions and then check their sites to see when they start new contests.
I also follow blogs that I enjoy reading and enter their contests as well. I won a gift certificate last year to Party Box Design on a blog and was able to get the baby's birthday invitations designed for free. Some blogs have more complicated entry processes like tweeting, following their Pinterest boards, liking them on Facebook and others only require a simple comment.
I like Pinterest contests and essays best because they take a certain creativity. The Ellen Show frequently has essay contests with fantastic prizes. I made it to the top 20 of a recent Pinterest contest to win a Whirlpool fridge!
Reading the fine print:
Read those Official Rules. Really. At least the parts that tell you how many times you can enter, how long the contest lasts, how the winners will be contacted and what it is exactly that you're entering to win.
Pay attention to how many times you can enter. I steer away from contests that tell me I can enter "up to 100 times a day". 'Ain't nobody got time for that! I prefer contests that only allow one entry per person/email address. This really evens the playing field.
Look at the starting and ending dates of the contest. Try and get in on the beginning of the contest if you are able to enter once a day to give you the best odds. I've entered every single day for the HGTV Dream Home contest; technically twice, because they let you enter at both HGTV.com and Frontdoor.com. They also offer a flooring contest from Lumber Liquidators & another for a GMC vehicle. I entered them all, every day of the contest so my odds are as great as they can possibly be! Of course, I'm in the mix with millions of others, but remember, someone has to win! Why not me? (or you!)
Some contests will ask for a code or something from a proof of purchase but there are often alternate ways of obtaining the entry (some as easy as just clicking a link that will supply you with a code without a purchase).
Watch those clickable boxes at the end of the entry form! If you don't want to receive a bunch of unwanted spam or junk mail or accidentally sign up for something you don't want (like a magazine subscription). Make sure you know what you've clicked (sometimes the boxes are already clicked and you need to unclick them each time).
Find your favorite stores and internet shops on Facebook and Pinterest and see if they are running any online contests.
Magazines often have contests or sweepstakes so a quick online search of your favorites should let you know what is available to enter.
Your local radio station probably has call-in contests (that's how I won the $50 Macy's card) but they often have online sweepstakes as well (that's how I won the Disney trip!).
Blogs are great place to enter and depending on the number of readers/entrants, the odds can be pretty good! Just over the weekend, I won a bottle of cleaner for stainless steel appliances and a microfiber cloth from Tidy Mom. We don't have stainless steel appliances in our apartment but our new house does *wink!*.
Last of all, good luck! Be consistent with your entering, have fun and have hope. Don't get discouraged if you don't win anything. I enter hundreds of contests and have only won a handful but I have my fingers crossed for a big one someday!