2027 Chicago mayoral race piquing interest of these notable names

The national political focus this year will be on the 2026 congressional midterm elections and whether Republicans will cede one or both chambers to emboldened Democrats.

Locally, we’ll be watching spirited March primary races for retiring U.S. Sen. Dick Durbin’s seat, a GOP challenger to take on governor and presidential aspirant JB Pritzker in November, several open congressional slots and a battle for Cook County assessor.

But those of us seasoned in Chicago’s political caldron are already looking ahead to our favorite broth: the next tasty mayor's race. Election Day will be Feb. 23, 2027.

Conventional wisdom tells us Mayor Brandon Johnson, based on dismal poll numbers and ongoing city problems, may be heading for a one-and-done term — the same fate that befell Lori Lightfoot.

But Chicago could be blessed with the strongest potential field of savvy, experienced and battle-tested replacements I’ve ever seen — any one of them ready, on Day 1, to tackle daunting challenges head-on by finally downsizing bloated city and sister agency bureaucracies, streamlining services, tweaking labor agreements, cutting unnecessary permitting red tape, lowering confiscatory taxes where possible and fighting crime effectively.

Those taxpayer- and business-friendly imperatives, along with improving schools and protecting vital social services, are the keys to righting the city’s sinking fiscal ship, and retaining and attracting residents and companies.

The mayoral field is by no means settled, and it could easily grow, but there are five clearly interested, albeit not officially announced, challengers: U.S. Rep. Mike Quigley, Cook County Treasurer Maria Pappas, Illinois Comptroller Susana Mendoza, Illinois Secretary of State Alexi Giannoulias and Chicago Ald. Bill Conway (34th).

Quigley’s name doesn’t jump off the page, but that’s the point. He isn’t a show horse — he’s a workhorse who’s been a fixture in Illinois politics for decades, first as a progressive Cook County commissioner who crafted an enlightened good government reform package and since then as the U.S. House representative for much of the North Side and northwest suburbs.

His record shows an ability to navigate complex policy terrains, from intelligence to infrastructure, and to work with colleagues across ideological lines.

He’s not bombastic. He’s not flashy. But he knows how government works — and crucially, how to make it work.

So does Pappas, Cook County treasurer since 1998 and before that a Cook County board member.

She’s a Mensa-smart, creative and innovative maverick whose office has shined the first real bright light on the dark world of property taxes, and she understands the revenue flows and levers of finance that make or break municipal governance.

Pappas, unlike Quigley, is flashy and stylish but just as substantive. Her liabilities? Sharp-tongued, quirky, unafraid to ruffle feathers and 76 years old. But with the energy of a teenager.

Mendoza’s track record is one of administrative reform, financial acumen and Democratic party insider chops. As Illinois comptroller — the state’s chief fiscal officer — she’s grappled with hemorrhaging budgets and political dysfunction.

Mendoza also previously served as Chicago’s city clerk and as a state legislator, giving her a blend of local- and state-level understanding Chicago desperately needs. She knows how money and the political game work, and how to flatten out dysfunction. In an era where Chicago’s finances seem to be on a treadmill straight to trouble, that’s not just reassuring — it’s essential.

Giannoulias, formerly the state treasurer and one of former President Barack Obama’s basketball buddies, has quietly built a profile and campaign war chest that could translate surprisingly well to City Hall. He combines executive management experience with big-city roots, and unlike many statewide officials, he actually knows Chicago.

His tenure at the secretary of state’s office has given him a crash course in running a large bureaucracy, dealing with constituent issues and handling logistics — all core skills for managing the nation’s third-largest city.

Conway is the wildcard in this group — young, hungry and short on experience, but with a blend of private sector savvy and recent public sector service on the City Council. He’s been a leading critic of Johnson while building relationships across City Hall, and thanks to his billionaire father, he has the financial backing most politicians only dream about.

Conway’s the candidate of those who think it’s time for a generational shift, and his endorsements from major labor and political figures suggest he’s not just a wealthy newbie with a Rolodex — he’s someone who, despite a lack of managerial experience, could grow into the job.

As you can probably tell from my assessment, Chicago’s next mayor’s race hasn’t felt this interesting or substantive in a long time. Not a clown car of has-beens and sacrificial lambs who perished at the political altar of a Daley, or names tossed around because they have clout and clever consultants.
That portends a campaign that merits close attention, and perhaps spawns a conundrum: Who the heck to vote for?

Andy Shaw is a retired Chicago political reporter and good government watchdog.