[1] When RedEye appeared, it was in direct competition with another paper Red Streak, which the Tribune's Chicago competitor the Sun-Times began publishing at the same time.

According to Sun-Times publisher John Cruickshank, Red Streak was only launched "to stop [the Tribune] from gaining a foothold in the paid tabloid market".

In February 2007, after NewsCorp launched a late-night talk television program on Fox News entitled Red Eye, the Tribune Company filed a federal trademark infringement lawsuit.

[6] As compared with mainstream newspapers, RedEye strongly emphasized pop culture and entertainment news, humorous or lighthearted rather than serious columns, and flashy graphics and large pictures.

Like the Chicago Sun-Times, RedEye is a tabloid-format newspaper, oriented vertically rather than horizontally and with a front page consisting only of a large picture and a banner headline.