Chicago, IL
Executive Assistant jobs in Chicago, IL
7 open roles from 6 employers. Checked Oct 6, 2026.
What these openings look like
6 employers are hiring here: Lurie Children's Hospital, Cushman & Wakefield, Nexstar Media and Vizient. Every one publishes a pay range, and they run $24.00 to $39.24 an hour. Every posting is full time. The most recent went up on Sep 28, 2026.
Every listing links to the employer's own application. Nothing is posted here on their behalf, and nothing is reposted from anywhere else.
Open roles
Executive Assistant
Posted Sep 28 · Verified Oct 6
Executive Assistant
Posted Sep 15 · Verified Oct 6
Executive Assistant
Posted Sep 14 · Verified Oct 6
Executive Assistant
Posted Sep 14 · Verified Oct 6
Executive Assistant
Posted Sep 11 · Verified Oct 5
Executive Assistant
Posted Sep 4 · Verified Oct 6
Executive Assistant
Posted Aug 4 · Verified Oct 6
What it pays here
Only some employers publish a range. These are the ones that did, as written in their own postings:
- $24.00–$39.24 an hour
- $72,250–$85,000 a year
- $30.00–$34.00 an hour
- $68,500–$116,300 a year
- $68,000–$88,000 a year
- $85,825–$107,282 a year
What they ask executive assistant candidates here
Drawn from the 7 open postings on this page. The ones that come up across several employers are near the top.
Tell me about the most senior leaders or faculty you have supported. What did a typical week look like?
What they are checking: Whether their five years of executive support matches the level and pace of this role.
How do you manage several Outlook calendars at once without double-booking or dropping something?
What they are checking: Practical calendar skill, which the posting calls out as expert-level.
Two leaders you support both need the same hour, and both say it is urgent. What do you do?
What they are checking: Judgment and diplomacy when priorities collide and there is no clear rule.
Tell me about a workflow you improved for an office. What changed and how did you know it worked?
What they are checking: Whether they improve processes on their own, as the posting asks, instead of just keeping up.
Describe a complex document, presentation or spreadsheet you built from scratch.
What they are checking: Real depth in Word, Excel and PowerPoint beyond basic formatting.
How do you handle a task when your leader gives you very little direction?
What they are checking: Comfort with ambiguity and the ability to move work forward without hand-holding.
Tell me about a time you had to manage other people's work through a confusing or changing situation.
What they are checking: Ability to steady others, which the posting lists as a requirement.
How do you keep track of deadlines when ten things are due this week?
What they are checking: A real system for organizing work, not just a promise to stay on top of it.
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