Deep Space Nine was originally acquired for viewing/distribution by WGN (and/or affiliates) which was Channel 9 in the Chicago area. Coincidence?
I left the Chicago area in 1990, and at that time, WPWR Channel 50 was carrying TNG. They didn't stick with the franchise?
Regarding syndication, apparently WGN pulled off a feat and stopped letting all the big series pass them by. Before DS9, WPWR-50 had gotten TNG, Baywatch, and Highlander. After then? WGN got DS9, Hercules, Xena, and every Tribune series (obvious why). WGN had more spending power than WPWR. They got the WB and now CW affiliation. They're still affiliated with the Cubs, Bulls, and now air Blackhawks games (since that idiot owner of their finally died and his son got with the 20th century and started televising games), air some White Sox games (split with WCIU. All these teams air about half or more of their games on the RSN).
WPWR was great for many years with syndicated series and syndicated cartoons. They became the UPN affiliate and were one of the stations Fox bought around 2000 or so. It's been downhill for them ever since. After UPN ended, they became the affiliate of that junkbin of a network My Network TV. The dual-ownership (WFLD & WPWR) ran the station into the ground (WFLD has taken a nosedive too. Their news operation is in shambles and is a complete joke with high turnover behind-the-camera, distant last in the ratings for many years, they have idiots running the controls [messed with the signal right as the Giants won the World Series. Literally everything's fine til the last at bat, numerous weather warnings for non-existent weather during the World Series]. IIRC WPWR was always better-run back in the day but WFLD's quality has definately gone down the past several years). WFLD dumped many shows it no longer wanted on WPWR. WFLD & Fox used the channel as its garbage can. It's quite sad to see it now (judge shows 7 days a week, crappy MNTV remnant syndication, AHL hockey). WPWR-50 did have the strip-synd reruns of TNG thru IIRC 1996.
Off the top of my head, the rest of the syndicated series in the Chicago market...
* WGN: Vanishing Son, Universal Action Pack, Adventures of Sinbad, Nightman, Adventure Inc, The Lost World. Everything except DS9 IIRC was 2-weeks behind due to WGN laziness with splitting their signal between WGN & WGN America. I'm not sure why DS9 was exempt from that (it aired Sundays in the first 3 seasons, Saturdays in the back 4 seasons as part of a block with Hercules, Xena, Earth: Final Conflict).
* WPWR: PTEN series (Babylon 5, Kung Fu: TLC, Time Trax, Pointman), Baywatch Nights, Tracker, Highlander: Raven, V.I.P. Amazon.
* WCIU: Conan, Tarzan, Flipper, back 2 seasons of Poltergeist: The Legacy. I think they had the Mortal Kombat series. They clearly got what was left, what WGN & WPWR passed on. The station's original lineup resembled METV + Svengoolie. Later on they added Stooge-a-Palooza before both ended up being switched over to the Me-channels.
* WFLD Fox-32: syndicated reairs of Stargate SG-1, The Outer Limits, 2 seasons of Poltergeist: The Legacy. A pretty stupid move because so often it ended up being pre-empted for baseball or football. Actually seemed worse than WGN for pre-emptions.
ABC-7 actually had Relic Hunter.