A photo of the DraftKings headquarters from March 26, 2019 in Boston, Massachusetts. (Photo by Darren McCollester/Getty Images for DraftKings)

Five major sportsbooks that sued the City of Chicago earlier this week to stop a new tax on online sports wagering that went into effect Thursday withdrew a request for a temporary pause Wednesday after the city issued the companies licenses to ensure continued operations. 

However, they will still pursue their lawsuit, arguing the new law is at worst unconstitutional and at best unclear.

Cook County Board President Toni Preckwinkle and Ald. Brendan Reilly (42) are competing in the Democratic primary for board president. [Preckwinkle photo found on president's office social media | Reilly picture by Don Vincent/The Daily Line]

As downtown Chicago Ald. Brendan Reilly (42) makes a bid to unseat Cook County Board President Toni Preckwinkle in the upcoming March Democratic Party primary election, he has built an immense fundraising base to rival the longstanding county executive, who is seeking a fifth term in office.

Ald. Bennett Lawson (44) speaks during a City Council meeting on March 12, 2025. [Don Vincent/The Daily Line]

Ald. Bennett Lawson (44), who has served as acting chair of the powerful Committee on Zoning, Landmarks and Building Standards for roughly half of Mayor Brandon Johnson’s term, is calling on the mayor to make a chairmanship official before he holds any more zoning committee meetings.

Members of the Chicago Alcohol Tax Coalition speak to the media at Off Color Brewing's The Mousetrap on Dec. 15, 2025. [Michael McDevitt/The Daily Line]

As the city prepares to enforce a new method for taxing retail sales of beer, wine and spirits at grocery stores, liquor stores and corner stores at the turn of the new year, the industry is calling for a delay to ensure businesses can comply with the changes.

Flanked by Ald. Leni Manaa-Hoppenworth (48) on the left and Ald. Rossana Rodriguez-Sanchez (33) on the right and among other progressives, Mayor Brandon Johnson signs two executive orders at City Hall on Dec. 23, 2025. [Mayor's Press Office]

Mayor Brandon Johnson signed two executive orders last week before allowing the adoption of an annual budget crafted and passed by a coalition of alderpeople opposed to various components of his initial budget proposal. 

Both executive orders are aimed at mitigating the effects of parts of the budget. The first executive order would place guardrails around the sale and collection of municipal debt to protect consumers from predatory practices, as the alternative budget plan includes a proposal to sell about $1 billion in uncollected debt owed to the city to a private party, a sale that was estimated by the alternative caucus to bring in at least $89.6 million. 

The second executive order would restore a cap on Chicago Police Department overtime spending that was in Johnson’s annual management ordinance proposal but omitted from the substitute version passed by the City Council.

A rendering of the proposed four-building development at 3746-66 S. Michigan Ave. is shown. [Chicago Department of Planning and Development]

The Chicago Plan Commission last week approved residential developments in South Shore and Douglas and a proposed cannabis dispensary in the West Loop.

Cook County Assessor Fritz Kaegi and Lyons Township Assessor Patrick Hynes are pictured. [Campaign social media]

Cook County Assessor Fritz Kaegi still has an on-hand campaign cash advantage over his Democratic Party challenger heading into the 2026 primary in March, but the incumbent assessor has been outpaced in fundraising as of late, according to state board of elections data.

Mayor Brandon Johnson presides over a City Council meeting on Dec. 16, 2024. [Don Vincent/The Daily Line]

The City Council on Friday and Saturday completed a more than two-month trek to passing a budget, with a rival revenue proposal, amended appropriations ordinance and a revised management ordinance being approved by a coalition of at least 30 alderpeople in an extraordinary show of council independence.

Mayor Brandon Johnson is pictured at a City Council meeting on Dec. 16, 2024. [Don Vincent/The Daily Line]

The City Council delayed final votes on the revenue side of the 2026 budget Thursday, setting them up to be voted on alongside the appropriations side of the equation at a Friday council meeting at the earliest. 

While proponents of the prevailing budget proposal, which was crafted by opponents of Mayor Brandon Johnson’s revenue plan, still fear a mayoral veto if their plans pass, Johnson on Thursday indicated an openness to forgoing a veto to avoid a government shutdown.

Budget Chair Jason Ervin (28) is pictured at a City Council meeting on April 17, 2024. [Don Vincent/The Daily Line]

The Committee on Budget and Government Operations on Wednesday evening voted 21-13 to approve an amended version of the 2026 annual appropriation ordinance that incorporates changes made on the revenue side by a group of alderpeople opposed to Mayor Brandon Johnson’s original plan.

The approval came despite the mayor’s budget team presenting an analysis of the new revenue ordinance, which passed the finance committee Tuesday, that claimed the rival revenue plan would leave the 2026 budget about $163 million short.

Ald. Bill Conway (34) is pictured at a City Council meeting on Feb. 26, 2025. [Don Vincent/The Daily Line]

The City Council Committee on Finance passed two bond authorizations on Tuesday, ignoring calls from the committee’s vice chair to delay consideration of one and approving an amended version of a second one, forwarding two key parts of Mayor Brandon Johnson’s 2026 budget plan.

Ald. Nicole Lee (11) speaks at a special City Council meeting on Feb. 26, 2025. [Don Vincent/The Daily Line]

A coalition of alderpeople behind a competing 2026 budget proposal unveiled a revised version of their revenue measure on Tuesday, and the Committee on Finance advanced the revenue portion of the plan 22-13. 

The latest version of the group’s alternative revenue ordinance (SO2025-0021719) is different in myriad ways from a version introduced last week.  

Mayor Brandon Johnson speaks at a press conference on Dec. 15, 2025. [Livestream]

Budget negotiations broke down Monday between the mayor and members of a coalition of mostly moderate alderpeople that are behind an unprecedented alternative budget proposal.

Mayor Brandon Johnson told reporters after that the alderpeople he met with refused to share the latest version of their alternative budget plan with him and his team, while the participating alderpeople said the mayor’s refusal to commit to not veto their proposal if it does not contain a corporate head tax caused the stalemate.

City Hall is pictured. [Don Vincent/The Daily Line]

The Chicago Plan Commission on Thursday will consider residential developments in South Shore and Douglas and a proposed cannabis dispensary in the West Loop.

The commission will meet at 10 a.m. in Room 1103 on the 11th floor of City Hall.

Ald. Andre Vasquez (40) attends a City Council meeting on March 12, 2025. [Don Vincent/The Daily Line]

In addition to a majority of the City Council introducing a substitute revenue ordinance to fund the 2026 budget last week, a substitute to the annual management ordinance was also introduced that includes a provision that would give the council more data and resources to study their own budget proposals.

The substitute management ordinance (O2025-0021709), introduced by Ald. Andre Vasquez (40), would require the city budget office to furnish more detailed information when presenting the mayor’s annual budget recommendation and when providing the council with the mid-year budget report.