Three of the flights had actually taken off within 10 to 15 minutes of their planned departure times.
( ( Three ( of ( the flights ) ) ) ( ( ( had actually ) ( ( taken off ) ( within ( ( ( ( 10 to ) 15 ) minutes ) ( of ( their ( planned ( departure times ) ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NP (CD Three)) (PP (IN of) (NP (DT the) (NNS flights)))) (VP (VBD had) (ADVP (RB actually)) (VP (VBN taken) (PRT (RP off)) (PP (IN within) (NP (NP (QP (CD 10) (TO to) (CD 15)) (NNS minutes)) (PP (IN of) (NP (PRP$ their) (JJ planned) (NN departure) (NNS times))))))) (. .)))
Within 10 to 15 minutes of their planned departure times, three of the flights had taken off.
( ( Within ( ( ( ( 10 to ) 15 ) minutes ) ( of ( their ( planned ( departure times ) ) ) ) ) ) ( , ( ( three ( of ( the flights ) ) ) ( ( had ( taken off ) ) . ) ) ) )
(ROOT (S (PP (IN Within) (NP (NP (QP (CD 10) (TO to) (CD 15)) (NNS minutes)) (PP (IN of) (NP (PRP$ their) (JJ planned) (NN departure) (NNS times))))) (, ,) (NP (NP (CD three)) (PP (IN of) (NP (DT the) (NNS flights)))) (VP (VBD had) (VP (VBN taken) (PRT (RP off)))) (. .)))