Romania's Halep, 23, beat Belarusian Victoria Azarenka 6-3 4-6 6-4 in a rain-interrupted match in New York.
Pennetta, 33, capitalised on two-time Wimbledon champion Petra Kvitova's inconsistency to win 4-6 6-4 6-2 and reach her second US Open semi-final.
Roberta Vinci and Serena Williams will contest Thursday's other semi-final.
With both Pennetta and her compatriot Vinci in the last eight, two Italian women have made the last four of the same Grand Slam tournament for the first time in the Open era.
Former world number one Azarenka, who spent 51 weeks as world number one earlier in her career, is climbing back up the rankings after a series of injuries over the past two seasons.
Halep looked in danger as her 26-year-old opponent came into the third set with momentum after winning the second in impressive style.
But a rain delay took the players off court for an hour and 25 minutes and Halep revived to reach the US Open semi-finals for the first time.
"I got behind the baseline in the second set and had to to do a lot of running. That break helped me. Thanks, God, for raining," she said.
Pennetta's New York love affair
In 38 appearances at the other three Grand Slam events, Pennetta has made the last eight just once.
However she has made the quarter-finals six times in seven years at Flushing Meadows and made only 16 unforced errors to Kvitova's 60 to progress to the semi-finals for the second time in New York.
"The second set I was really in trouble, but I just kept going," Pennetta said after her win over Kvitova, 25. "It's unbelievable."
She has won three of her four previous meetings with Halep.
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