Be careful going to this page, there is a REALLY annoying “chat” pop-up that keeps coming up, even though you close it repeatedly.
Prize(s):
Grand Prize: $7,500 scholarship and $500
Second Place: $3,000 scholarship and $500
Third Place: $2,000 scholarship or $500
Two runner up prizes of $100 Amazon gift certificates
How to Enter:
Tell us how a degree from WGU could [...]

Greatest Reviews is holding a contest with multiple prizes including a bunch of advertising, some cash, and other various items.
Prizes:
1. 2 One hour’s consultation time for blogging sponsored by The University Kid ( 2X50$=100$)
2. 1,000 copies of $1 e-Book sponsored by BlogPremiere (1000$ )
3. 3 Sidebar 125 X 125 ADS for one month (3X15$=45 $)
4. [...]

Phil over at Contest Blogger has released seven new websites, each focused on a theme:
Art Contests
Automobile Sweepstakes
Baby Contests
Canadian Contests
Photo Contests
Recipe Contests
Writing Contests
Check them out and enter some contests.
Also, you can get up to eight entries into his monthly $100 contest just by linking to these websites.

Prize(s):
WEEKLY PRIZES (A total of six (6) Weekly Prizes will be awarded in this Sweepstakes (awarded as one [1] Weekly Prize per Weekly random drawing): Each Weekly Prize shall consist of a check in the amount of $200.
GRAND PRIZE (One (1) Grand Prize will be awarded): The Grand Prize consists of a check in the [...]

Huge contest going on over at DNXpert.com:
Contest Steps And How To Earn Entry Points:

Subscribe to DNXpert newsletter using the form above - required. (1 point )
Blog about this contest (10 points)
Blog about this contest and include the Prize Recap list in your post. You can download the Prize Recap list code here. (20 points)
Follow the [...]

Contest URL: Proudest Moment Photo Contest
Prize(s):
1st Prize - $150 Cash & a Church Hill Classics photo frame up to 11” x 14”
2nd Prize - $75 & a a Church Hill Classics photo frame up to 8” x 10”
How to Enter:
Send us a photo and a brief description telling us about your proudest moment.
Visit the CHC [...]

The Net Fool is holding a huge contest on his blog, here are the prizes:
Cash

$250 Cash from PepperJam Network
$50 Paypal Cash from Ades Blog
$25 Paypal Cash from Sohaib Thiab

Web Hosting

1 Year Web Hosting from Young Online Millionaire

WordPress Themes & Design

$500 Custom Premium Blog Design from Pixel Jig
2 Copies of the Revolution WordPress Theme from Brian [...]

BigBuckSurveys.com is giving away a Hummer H3 or $50,000 cash!
Just head over to BigBuckSurveys.com and fill out a little bit of info. They’ll take you to a survey to fill out and you’re entered. I think they also send you occasional emails for more surveys but you can always unsubscribe after that.
You must be a [...]

Blog-Almighty is holding a contest with some various prizes:
(1) Grand Prize Winner
* $30 via PayPal
* 500 EntreCard credits
* One month advertising slot (125×125) on our sidebar (currently priced at $15 a month)
(2) First Runner Up
* $20 via PayPal
[...]

Winning the Web is holding a contest giving away a ridiculous amount of prizes. And this isn’t your usual “$13,000 in prizes” and it turns out to be all advertising that’s “worth” $13,000. They’re giving away over $13,000 of real prizes!
Cash
$650 Cash from Azoogle Ads
$500 Cash from PepperJam Network
$250 Cash from NeverblueAds
$200 Cash from BidVertiser
$200 [...]