Gambhir and Kallis also shared an unbeaten 50 runs stand in 38 balls to steady Knight Riders’ chase.
Chennai’s Ravichandran Ashwin struck to dismiss Brendon McCullum and give Kolkata Knight Riders early blow in chase of 140.
Earlier, Kolkata Knight Riders produced a superb bowling display to restrict Chennai Super Kings to 139/5.
Skipper Dhoni 34 off 30 balls and Albie Morkel 13 off 8 balls remained unbeaten at the crease. The duo added 21 runs in 2 overs to take Chennai to a modest total.
Jacques Kallis claimed two wickets while Brett Lee and Sunil Narine took wicket apiece to stutter Chennai.
Raina was in good touch, making 44 off 34 balls with the help of four fours and a six. Chennai Super Kings stuttered in the innings as they lost wickets at regular intervals.
Dwayne Bravo was the third man to go when Iqbal Abdulla took the simple catch at long-on off Jacques Kallis.
Bravo and Suresh Raina added 42-run stand for the third wicket to steady Chennai innings after suffering the dismissals of the openers.
Chennai lost their second wicket in the form of David Hussey when he got run out in a mix up with Suresh Raina. Brett Lee struck in his first over to remove Faf du Plessis cheaply.
Du Plessis failed to continue his good run as he scored three runs before going back to the pavilion.
Earlier, Chennai skipper Mahendra Singh Dhoni won the toss and opted to bat against Kolkata in the 41st of the tournament.
Kolkata decided to retain the same playing eleven that thrashed Royal Challengers Bangalore by 47 runs.
Chennai Super Kings: Faf du Plessis, Subramaniam Badrinath, Michael Hussey, Suresh Raina, Ravindra Jadeja, MS Dhoni, Dwayne Bravo, Albie Morkel, Ravichandran Ashwin, Shadab Jakati, Yo Mahesh
Kolkata Knight Riders: Brendon McCullum, Gautam Gambhir, Jacques Kallis, Yusuf Pathan, Manoj Tiwary, Debabrata Das, Laxmi Shukla, Brett Lee, Rajat Bhatia, Sunil Narine, Iqbal Abdulla