In the first incident, police said a 29-year-old man was sitting inside of his parked 2020 Range Rover at about 1:44 a.m. in the 500-block of North Rush Street when four suspects approached on foot and displayed handguns.
Police said they demanded his car and the victim complied. The suspects then fled in an unknown direction.
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No injuries were reported and Area Three detectives are investigating.
The second carjacking occurred at about 2:11 a.m. in the 1100-block of West Van Buren Street.
A 42-year-old man was in a parked 2016 gray Dodge Durango when police said three suspects got out of a black SUV, possibly a Kia Soul. The suspects were armed and demanded the victim get out of the car, police said.
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The victim complied and the suspects drove away in the Durango with a fourth suspect driving the Black SUV.
No one is in custody and Area Three detectives are investigating.
Police have not linked the West Loop carjacking to the earlier incident in River North.