The way that squids get pregnant is through sexual intercourse just like humans get pregnant through sexual intercourse.
The male squid has a penis which he sticks into the female squids Vagina and then the male squid releases sperm into the female squid and then when the eggs fertilize with the male squids sperm the female squid becomes pregnant with a baby squid.
The male squid has a tiny penis which produces sperm and they just have sex just like humans, dogs and cats and other animals do.
The pregnancy can be different though but the sexual intercourse is nearly the same as humans.