Bollinger registered splendid figures of four for 13 in four overs, including a maiden, as the defending champions were skittled out for a paltry 104 in 19.2 overs.
They will meet Mumbai Indians [ Images ] in Sunday's final.
Deccan pacer Ryan Harris had taken three for 29 to restrict Chennai Super Kings [ Images ] to 142 for seven in their 20 overs, but their batsmen failed to come good.
Andrew Symonds [ Images ] was the top-scorer with 23 from 22 balls; he was caught at deep midwicket off R Ashwin.
Adam Gilchrist [ Images ] scored 15 before he was caught at square leg; it continued his poor run with the bat in the tournament, having made just one half-century in 15 matches.
The Chennai top order also failed to fire before Mahendra Singh Dhoni [ Images ] (30 from 32 balls) and S Badrinath (37 from 41 balls) steadied the innings with a 52-run partnership in 51 balls for the fourth wicket.
Anirudha Srikkanth hit a couple of sixes for a quick 24 from 15 balls as Chennai scored 26 runs from the last two overs to post a respectable total.
Chennai Super Kings:
The struggling Matthew Hayden [ Images ] got two lifelines in the first two overs of the innings but failed to prosper.
The left-hander, on zero, hit Andrew Symonds straight to RP Singh [ Images ], at cover, who grassed an easy opportunity. In the next over, Hayden got another reprieve on four, when his outside edge off pacer Ryan Harris was dropped by T Suman in the gully region.
It was third time lucky for Deccan when Hayden was taken by Symonds at covers off Harris and was dismissed for eight.
Murali Vijay [ Images ] also joined his team mate in the dug out soon after when he was trapped leg before wicket for 15, in the third over of the innings by Harris.
Deccan's fielding let them down yet again as Suman dropped another easy catch. Suresh Raina [ Images ] (0) tried to play Harris through the leg side but got a leading edge which was put down by Suman in the gully.
Raina also didn't survive long enough to profit from that drop. He made just two before he tried to chip down the wicket to Symonds but got an outside edge and was taken by wicketkeeper Adam Gilchrist.
Having elected to bat, Chennai were struggling at 31 for three in five overs, courtesy a brilliant opening spell from Harris.
Captain Mahendra Singh Dhoni slammed a wide delivery past the point fielder for his first boundary, in the sixth over of the innings. S Badrinath got his first boundary when he hit Harmeet Singh straight down the ground to take the total to 62 for three after ten overs.
It was Harmeet who got the big wicket of Dhoni, out for a sedate 30 from 32 balls. The Chennai captain was foxed by the slower leg cutter from the pacer as he looked to play the cut shot but got an edge and was taken by Rohit Sharma at gully.
Badrinath looked to lift the tempo and hit Harmeet over mid-on for a four, followed by a straight six off Pragyan Ojha [ Images ] in the next over.
But Ojha finished his spell on a high when he got the wicket of Albie Morkel (4), caught at long-on, to reduce Chennai to 96 for five after 15 overs. That was Ojha's 50th wicket in the IPL as he finished with wonderful figures of one for 27 in four overs.
Badrinath struggled to 37 from 41 balls before he was run out as he tried for a quick single off an inside edge.
Anirudha Srikkanth provided the impetus at the end as he hit two sixes in the final two overs for a quick 24 from 15 balls.
Harris cut short his innings when he was caught at mid-on as he attempted to take on a short delivery. He finished with impressive figures of three for 29 to restrict Chennai to 142 for seven in their 20 overs.
All the bowlers came to the party for Deccan, with Symonds taking one for 18 in his four overs, while Harmeet took one for 22.
Deccan made a cautious start as R Ashwin conceded just one in the opening over and Doug Bollinger followed it up with a maiden over.
Adam Gilchrist broke the shackles when he stepped down the wicket and hit Ashwin for a six and pulled Bollinger for a boundary in the next over.
But Bollinger crippled Deccan by claiming two wickets in his third over.
Deccan captain Gilchrist failed yet again with the bat. He made 15 from 20 balls before he was caught at midwicket by Anirudha off Bollinger.
T Suman started off with a boundary but he was brilliantly caught by Raina in the covers for four as Deccan were reduced to 23 for two after six overs.
Rohit Sharma also threw his wicket away when he chipped Albie Morkel straight to Muttiah Muralitharan on the long-on boundary for two.
Herschelle Gibbs [ Images ] and Andrew Symonds failed to get going as Deccan struggled to 43 for three after ten overs, having hit just three boundaries and a six.
Shadab Jakati [ Images ] then made life more difficult for Deccan as he claimed the wicket of Gibbs. The Deccan opener, who made 18 from 26 balls, tried to cut Jakati but was undone by the slow pitch and ended up inside edging it back on to his stumps.
Symonds hit a much-needed boundary in the 12th over when he cut Bollinger through the point region as Deccan crawled past the 50-run mark in that over to register the slowest 50 in this year's tournament.
Deccan's woes mounted when Monish Mishra was stumped in Jakati's next over for two as Deccan left reeling at 58 for five after 13 overs.
Finally, Symonds decided it was time to break the shackles and hit Jakati for back-to-back boundaries to get 17 runs from the 15th over, leaving Deccan to get 62 from the last five overs.
But Ashwin dashed off any hopes Deccan had by getting the wicket of Symonds in his final over; The Australian made 23 from 22 balls before holing out to Murali Vijay at deep midwicket.
Off-spinner Ashwin once again impressed with the ball as he finished with one for 14 in four overs.
But it was Bollinger who stole the show with a four-wicket haul. The left-arm pacer claimed two wickets in his final over to finish with remarkable figures of four for 13 in four overs.
Harris tried to take on Bollinger but hit straight into the hands of Vijay for 15, and two deliveries later B Sumanth was beaten all ends by a yorker to be bowled for 16.
Muttiah Muralitharan, bowling from round the wicket, deceived Harmeet Singh with a quicker delivery to trap him leg before wicket for a duck.
Part-timer Suresh Raina finished off things when Pragyan Ojha lofted it straight to Bollinger at long-on.
Defending champions Deccan were bowled out for 104 in 19.2 overs and lost by 38 runs.
Chennai will take on Mumbai Indians in Sunday's final, while Deccan play Royal Challengers [ Images ] Bangalore in the third place play-off.
Gilchrist's poor form with the bat proved costly for Deccan as they did not get going in the first few overs before losing wickets regularly.
Chennai's strategy of playing the extra spinner paid off, with Ashwin taking one for 14, while Muralitharan claimed one for 16.