Three introductions from Chippa saw Nyiko Mobbie, Thamsanqa Sangweni and Peter Maloisane preferred from the loss at home to Mamelodi Sundowns on Monday afternoon.
Chippa should've gone in front on five minutes throughThabiso Lebitso though after staying onside, the attacker hesitated to get a shot away and had the opportunity spurned in the end.
As the midway period of the first half approached and the match beginning to open up, William Twala directed a low ball from the right-side by Thabo Moloi well over the top of target.
Twala was close again four minutes from the half-hour mark after a powerful shot from the inside-right of the area brought sharp reflexes off goalkeeper Rashid Watenga.
Substitutions from either side following halftime had Chippa introduce Anthony Laffor for Lebitso, while Callies removed Twala for Keorapetse Sebone.
Callies showed the same dominant effect that marred the first spell, and had the Chilli Boys stretch from a long ball to Thabiso Nkoana minutes from the restart, but he couldn't beat Watenga.
The Chilli Boys continued to hang on and broke the deadlock against the run of play inside 62 minutes when Sandile Mthethwa volleyed home a loose ball from point-blank range.
It was all the visitors thereafter and a second nearly came through a shot from range by Gregory Damons, but he struck the top of the net before Sebone headed over from close-range.
With Callies in search of the equaliser late on, Chippa introduced Oupa Manyisa for his debut ahead of Luvuyo Phewa.
However, the Chillis Boys sustained the pressure to claim victory and a spot in the final with the other semi-final between Mamelodi Sundowns and Tshakhuma Tsha Madzivhandila set to take place on Sunday.
Callies: Lesu, Moloi, Moeketsi, Menziwa, Pheko, Nkoana, Twala, Sauls, Tladi, Marebane, Sithole.
Subs: More, Mahlangu, Gumede, Rorwana, Natemba, Sebone, Sitayitai, Buthelezi, Bopape.
Chippa: Watenga, Nsabiyumva, Mobbie, Mthethwa, Sangweni, Kwem, Lebitso, Phewa, Konqobe, Hanamub, Maloisane.
Subs: Mtshali, Manyisa, Laffor, Mokhele, Nomandela, Jodwana, Eva Nga, Damons, Mdlinzo.