Deputy General Counsel, Transactions
Chicago Public Schools
Chicago, IL · Posted October 30, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about legal jobs
- Best cities for legal jobs #1 New York (854 openings)
- Best cities for legal pay after cost of living #1 San Mateo ($238k)
- Most requested AI skills in legal jobs #1 AI tools in daily work (3.9%)
- Employers with the most legal jobs #1 Morgan & Morgan (195 roles)
How AI is used in this kind of work
Among lawyers, AI is already used for some of the tasks. Measured exposure for lawyers: 17% (some).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
About the job
Chicago Public Schools (CPS) is a district on the rise, serving over 320,000 students in 500+ schools and employing over 44,000 people, most of them teachers. CPS has set ambitious goals to ensure tha