The one exception is the Chicago Bears, who, like other NFL franchises, are bound by network broadcasting contracts by the National Football League for the most part, though most teams license some of their preseason games for regional over-the-air broadcast through in-house syndication units; although the Bears' cable-originated games have occasionally aired on WGN-TV by arrangement with ESPN under NFL provisions pertaining to national cable telecasts within a franchise's home market.

Coverage of baseball games involving the Chicago Cubs has perhaps typified WGN-TV's programming identity, due to the popularity of the telecasts both locally and, as a superstation, throughout the Midwestern United States.

[15] On August 22, 2009, the Tribune Company transferred a controlling 95% interest in the team and its 25% stake in regional sports network Comcast SportsNet Chicago (now NBC Sports Chicago) to Thomas S. Ricketts (son of TD Ameritrade founder J. Joseph Ricketts) in a leveraged partnership arrangement – designed to prevent Tribune, which was in the midst of Chapter 11 bankruptcy protection proceedings due to the $13 billion in debt it accrued through Sam Zell's 2007 buyout and subsequent privatization of the company, from incurring taxes in an outright sale – for $845 million.

[18][19][20] On November 5, 2013, the Cubs exercised an option to opt out of their television contract with WGN-TV – which was originally set to end in 2022 – following the 2014 season, with the intent of seeking a higher-value deal for the next five-year contractual period.

As a result, on November 9, 1966, the Sox struck a five-year deal with Field Communications-controlled UHF independent WFLD-TV (channel 32, now a Fox owned-and-operated station) to televise the team's full slate of home and away games starting in 1968.

[25][26] Those rights were passed onto WSNS-TV (channel 44, now a Telemundo owned-and-operated station), as a result of then-owner Essaness Television Corporation signing a one-year agreement on August 3, 1972, that would see the competing independent acquire a package of at least 144 White Sox regular season games, beginning with the team's 1973 schedule.

Although WSNS-TV had exclusivity over the White Sox telecasts, WGN maintained an outsourcing agreement with that station, under which Channel 9 handled production responsibilities for the games on behalf of WSNS.

In December 1980, Channel 9 signed a partial broadcasting agreement with White Sox, which confined its game telecasts to the team's road games—a reduced schedule of 60 games—for the 1981 season.

)[28] Dissatisfied with the licensing fees it was receiving for the WGN telecasts, however, Reinsdorf and Einhorn (the latter being a former president of CBS Sports and founder of the defunct TVS Television Network syndicated sports service) decided to move the White Sox's telecasts to Sportsvision, a joint venture between the Reinsdorf–Einhorn partnership and Fred Eychaner, owner of upstart independent WPWR-TV (channel 60, now a MyNetworkTV owned-and-operated station on channel 50) through parent Metrowest Corporation.

(Due to low subscriber rates and resulting financial losses, Sox ownership sold Sportsvision to a venture of Cablevision Program Enterprises and The Washington Post Company in December 1983.

Jack Brickhouse, Lorn Brown, Milo Hamilton and Bob Costas were among those assigned to work as Bulls play-by-play announcers for the WGN telecasts, with Johnny "Red" Kerr serving as an analyst.

In connection with the out-of-court settlement between WFLD station management and the White Sox, through the same agreement signed on September 14, 1989 that resulted in that station also re-acquiring the local television rights to the Sox, the Bulls (which Reinsdorf – as part of Chicago Professional Sports Limited Partnership, a 23-member majority shareholder group that acquired portions of its 56% share of the team from shares owned by, among others, the estate of longtime owner Arthur M. Wirtz and New York Yankees owner George Steinbrenner – bought in March 1985 for an estimated $9.2 million) announced that it would move its local television broadcasts back to WGN-TV under a five-year deal, beginning with the 1989–90 season.

[33][34][37][38] The return of the Bulls to WGN-TV was a major boon for the station, as it overlapped with the six-season NBA championship dynasty that flourished during Michael Jordan's tenure with the team.

This marked the first time that Channel 9 had broadcast games from all five of Chicago's legacy professional sports teams during the course of a single season; the Bears simulcasts were not carried on WGN America due to conflicts that would be incurred with the NFL Network telecasts.

Among the Bears games shown on the station were simulcasts of ESPN-televised Monday Night Football broadcasts (including match-ups against the Dallas Cowboys on October 1, 2012, and against the Washington Redskins on September 23, 2019).

During the years leading up to the programming separation of WGN-TV and now-former national feed WGN America, the Illinois Derby and Hawthorne Gold Cup Handicap telecasts were shown exclusively over the Chicago area signal.

)[60][61][62] On February 19, 2015, Weigel terminated its agreement with Tribune to carry WGN-produced Cubs and White Sox telecasts, in an effort to limit scheduling conflicts with WCIU's then-recently launched early-prime time newscast (produced through a news share agreement with WLS-TV); the WGN-leased overflow broadcasts were moved to WPWR-TV – airing under the brand "WGN Sports on My50" – beginning with the 2015 Cubs and White Sox seasons.

This would allow WGN-TV to increase the amount of sports programming that it could air during the calendar year (albeit, with far fewer televised games for each of the contracted teams than it had previously been able to air during its first tenure as an independent between 1956 and 1995) and give it full over-the-air exclusivity over Cubs, White Sox, Bulls and Blackhawks telecasts, resulting in the termination of its outsourcing agreement with WPWR (which would concurrently become a primary CW affiliate through an agreement with parent company Fox Television Stations).

[70][71] The new restriction spurred a conspiracy and antitrust lawsuit that was filed by the Bulls (one of two NBA teams that voted against the proposal, along with the New Jersey Nets, then broadcasting over Secaucus, New Jersey–based superstation WWOR-TV) and Tribune Broadcasting with the United States District Court for the Northern District of Illinois on October 16, 1990, alleging that the league rules would harm the Bulls, their fans and WGN and that Stern's proposal was aimed at "phas[ing] out such superstations telecasts entirely in increments of five games each year over the next five years."

(The NBA contended the restriction was exempt from antitrust law under a provision of the Sports Broadcasting Act of 1961, which was deemed in later rulings to only be applicable to the sale or transfer a national game package to a television network and not those involving individual teams.

)[72][73] On January 26, 1991, Senior U.S. District Judge Hubert L. Will granted a permanent injunction in favor of the Bulls and WGN, prohibiting the league from instituting the policy on the determination that the NBA's superstation licensing restrictions were "a significant restraint of trade" in violation of the Sherman Antitrust Act.

However, criticism of the move from some subscribers led TCI to reverse course and retain the WGN superstation feed from affected systems in Illinois, Indiana, Iowa, Wisconsin and Michigan.

(Some TCI systems elsewhere would not reinstate WGN until as late as 1998, through an effort by Tribune and the superstation feed's uplink carrier, United Video Satellite Group, to take advantage of TBS's conversion into a hybrid basic cable network.

The move sparked concerns that WGN-TV's revenues from the Cubs telecasts would be impacted if the Cubs were forced to play a larger number of games against other Western Division teams based in the Pacific Time Zone, resulting in an increased number of games being shown in the late evening locally and potentially impact advertising revenue from the 9:00 p.m. newscast if it had to delay it after prime time more frequently because of the late baseball starts.

As such, beginning with the April 1 game between the Blackhawks and the Winnipeg Jets, WGN wound down its local sports coverage throughout the spring and summer of 2019 as the station's contracts with all four teams expired.

WGN-TV's contract with the Fire ended at the conclusion of the 2022 season as a result of Apple TV gaining exclusive worldwide rights to all MLS matchups for 10 years, beginning in 2023.

)[121] Even prior to the decision, WGN America had chosen not to air certain sports-related programming carried on the Chicago signal such as the Blackhawks' victory parade following its 2010 Stanley Cup championship win and a half-hour special paying tribute to the late Cubs player and broadcaster Ron Santo in 2011.

(In the respective cases, WGN-TV's coverage of Santo's funeral aired on the digital subchannels of selected stations owned by Tribune and its partner group Local TV, while the NHL Network provided a simulcast of the Chicago signal's feed of the Blackhawks' victory parade.)

All White Sox, Bulls and Cubs games televised on WCIU began to be syndicated to local stations in central Illinois and Iowa through the "WGN Sports Network" service beginning with each team's respective seasons in 2011.

Some games also air on MyNetworkTV-affiliated sister WNDY-TV (channel 23) due to pre-emption limitations included in The CW's affiliation contracts that also forced WGN to defer some of its sports telecasts prior to its 2016 disaffiliation from that network.