Understand it implies you know and accept possible negative outcomes. He decided to take his chances with the unpredictable weather for the camping trip.
Pro Tip 2/3
No Guarantee
Emphasizes that success isn't assured when you decide to proceed. She’s going to take her chances and audition for the lead role, even if it's a long shot.
Pro Tip 3/3
Opportunity Seeking
Suggests a proactive step towards an uncertain opportunity. I'm going to take my chances at the startup competition; it could be a big break.