[6] In 1998, the station was sold to Big City Radio, which also purchased WCBR-FM in Arlington Heights (also on 92.7) at the same time.

[3][12] Big City Radio also purchased WDEK 92.5 in DeKalb, Illinois, which was airing a locally programmed CHR format at the time, and switched it to a simulcast of WKIF and WKIE in early 1999.

[15][16] On January 12, 2001, Clear Channel's WUBT changed formats from rhythmic oldies to CHR as WKSC-FM "Kiss 103.5".

[17] At that time, Clear Channel filed suit against Big City Radio, alleging the "Kiss FM" branding used by WKIF and its simulcasts violated its national trademark.

[24][25][26][27] In 2004, Spanish Broadcasting System sold WKIF, WKIE, and WDEK to Newsweb Corporation for $28 million.

[33][34][35] In August 2012, WKIF changed their format to oldies, simulcasting WVLI 95.1 FM Kankakee, branded as "The Valley".