4 Best Executive Assistant Staffing Agencies in Chicago

Chicago runs on decisive leaders—and on the Executive Assistants who keep their calendars, travel, and inboxes humming. The snag? The market for seasoned EAs has never been tighter. Average salaries hover around $84k—roughly fifteen percent above the U.S. norm—because every CEO in town wants the same slice of talent.

If you’re an executive scrambling to replace a right-hand partner, or an EA ready to level-up your career, you’ve probably noticed another hurdle: most online “best staffing” lists lump Executive Assistants in with generic admin roles and overlook the boutique firms that live and breathe high-stakes support. Worse, many lists are written by the agencies themselves.

We went deeper—client surveys, third-party awards, candid Reddit threads—to build a truly independent ranking. In the pages ahead you’ll find:

• How we scored each firm on client satisfaction, candidate experience, specialization, and Chicago tenure.

• Punchy profiles of the seven agencies that rise to the top.

• A comparison table and salary snapshot so you can budget (or negotiate) with confidence.

• A practical checklist to help you choose the recruiter who fits your timeline, culture, and privacy needs.

Ready to meet the agency that can free you to focus on strategy—or the boss who finally values your skill set? Read on.

How we chose the seven stand-out agencies

Before we rank a single recruiter, you deserve to know the yardstick. Being transparent keeps this guide honest and helps you decide if our priorities match yours.

We reviewed more than two dozen staffing firms that place Executive Assistants in Chicagoland, then scored each one against five concrete pillars:

Client satisfaction and third-party awards. We leaned on data you can verify: ClearlyRated scores, Forbes “Best Recruiting Firms,” and multi-year “Best of Staffing” wins. Happy employers speak volumes.

Candidate experience. An agency that ghosts talent eventually hurts clients too. Reddit threads, Glassdoor reviews, and word-of-mouth stories weighed heavily in our ratings.

Depth of EA specialization. Firms that focus on executive support earned higher marks than generalist temp shops. We look for recruiters who understand gate-keeping, board prep, and inbox triage.

Chicago tenure and network strength. A recruiter with decades in River North knows which assistants just wrapped a contract at the Merc. Local roots translate to faster, better-fit shortlists.

Service breadth and speed. Temp-to-hire pipelines, confidential retained search, and the ability to drop a seasoned EA into a board meeting tomorrow all add real value.

We assigned point values to each pillar, weighted in that order. The composite score placed agencies one through seven.

Is it scientific? As close as the public data allow. Is it useful? Absolutely. It surfaces firms that deliver for both executive and assistant roles right now in 2026.

Meet the agency that tops the chart.

1. C-suite Assistants: boutique precision for C-level support

If you need an Executive Assistant who can glide from investor-deck edits to last-minute jet logistics without breaking a sweat, C-suite Assistants tops the shortlist.

Founded in 2003 by former banking executive Carol Coleman, the firm focuses exclusively on executive and personal support roles. No accountants, no marketers; just career gate-keepers and Chiefs of Staff who already speak the language of power corridors.

That focus pays dividends. Recruiters interview every candidate against a proprietary scorecard that covers diplomacy, anticipatory thinking, and tech fluency. By the time résumés reach your inbox, you’re looking at a curated trio, not a cattle call.

Although headquartered in New York, the team has spent more than fifteen years placing talent in Chicago’s finance, consulting, and high-growth tech scenes. Clients say the national reach is a secret weapon: when the perfect EA isn’t local, C-suite can persuade a standout in Austin or Atlanta to relocate.

Candidates praise the white-glove coaching: mock board-prep drills, salary negotiation tips, and a discreet ear when a current boss can’t know they’re job-hunting. That respect sparks loyalty, yet C-Suite warns that loyalty erodes when sustained excellence stops being noticed. Its playbook of executive assistant retention strategies—steady recognition, stretch assignments, and chemistry-based hiring—helps employers turn a standout first year into multi-year tenure.

In short, if your executive office demands confidentiality, polish, and a partner who “gets it” without a five-page brief, C-suite Assistants delivers boutique precision with Big Apple energy.

2. City Staffing: Chicago’s award-loaded local powerhouse

When you want a recruiter who knows the Loop like a cab driver and greets half the city’s EAs by first name, you ring City Staffing.

Launched in 1990 and still proudly woman-owned, the firm has woven itself into Chicago business life for more than three decades. That longevity shows up in hard metrics: multiple consecutive “Best of Staffing” wins for client and talent satisfaction, each one backed by ClearlyRated’s independent surveys. Clients rate the team 4.8 out of 5; candidates echo the same number. Consistency like that is hard to match.

City Staffing’s key advantage is speed without shortcuts. Because the recruiters maintain an active bench of pre-vetted assistants, they can place a temporary EA tomorrow or surface a direct-hire shortlist in a week. Yet every résumé still goes through a culture-fit screen, so you avoid the revolving-door syndrome that plagues many admin hires.

Versatility is another edge. The firm fills temp, temp-to-hire, and permanent roles across finance, nonprofits, and edgy creative shops. Whether your COO needs cover during maternity leave or your founder wants a long-term right hand, one phone call covers the bases.

Candidates value the human touch. Reviews praise recruiters for honest feedback, salary advocacy, and the courtesy of returning calls—no small feat in an industry known for radio silence. That goodwill pays employers back in loyalty: assistants placed by City Staffing tend to stay.

If you value hometown savvy, rapid turnaround, and a track record polished by trophies, City Staffing is the Windy City native you want in your corner.

3. Mack & Associates: four decades of culture-first matches

Some firms push résumés. Mack & Associates shapes careers.

Since 1984, this boutique, woman-owned agency has focused on one goal: pairing Chicago executives with administrative pros who thrive for the long haul. Their mantra is culture first, skills second, because a brilliant EA who clashes with the CEO’s style will exit faster than a CTA express.

The approach starts with deep listening. Recruiters probe not only technical chops but also communication style, decision-making pace, and even humor. That insight fuels placements that stick, a claim backed by a 4.9-star client rating drawn from more than six hundred third-party surveys.

Longevity breeds network power. After forty years, alumni refer alumni, and Mack often hears about top assistants weeks before they update LinkedIn. Hiring managers get a sneak peek at passive talent the competition never sees.

The firm handles direct-hire and temp-to-hire searches, making it a smart pick when you want to test a role before committing. Yet “temp” here doesn’t mean junior. Mack routinely fields candidates who have supported partners at Am Law 100 firms or chiefs at global consultancies.

Candidates praise the upbeat, human vibe: quick feedback, genuine career advice, and a recruiter who remembers your dog’s name. Employers feel the ripple effect in retention; the soft stuff pays off when an assistant stays past the critical first year.

If your leadership team values seamless chemistry as much as stellar PowerPoint chops, Mack & Associates proves that culture fit isn’t a buzzword; it’s a business strategy.

4. The Larko Group: rapid, reliable, and proudly women-led

Need an EA yesterday? The Larko Group has spent 30 years proving that speed never has to cost precision.

Founded in 1993 and now co-run by Amy Larko Falanga and Andrea Newman, this certified women-owned firm has served more than eleven hundred Chicagoland employers. Clients range from Fortune 500 headquarters on Wacker Drive to family-run real-estate firms in Oak Brook, yet the promise stays the same: accurate matches delivered quickly.

The engine behind that promise is a deep local database of office-support pros. Recruiters keep detailed notes on each candidate’s preferred industries, software skills, and commute tolerance. When a role opens, they can filter and call qualified EAs within hours, not days.

Larko’s team also refuses to play résumé roulette. Every shortlist is curated after live interviews that probe soft skills such as gate-keeping tact and crisis calm. The payoff shows in the numbers: online reviews average 4.7 stars, with employers praising “spot-on fit” and assistants applauding transparent feedback.

Versatility is another edge. Larko handles temp, temp-to-hire, and permanent placements, making the firm ideal when you need maternity-leave coverage now and a long-term EA next quarter. Their temp bench often features career admins with Big Four or Am Law pedigree, ready to step into board meetings.

If you prize quick action, meticulous vetting, and the chance to support a women-led Chicago business, The Larko Group covers every need, fast.

5. Beacon Hill Staffing: national muscle, local heart

Beacon Hill Staffing Group brings billion-dollar resources to a corner-office problem, yet its Chicago Associates division still answers the phone like a neighborhood shop.

Headquartered in Boston but planted firmly on LaSalle Street since the mid-2000s, Beacon Hill runs one of the largest administrative talent pipelines in the country. That scale matters when speed or volume is non-negotiable. Need three contract EAs to launch a satellite office next week? The team can tap a database of thousands in minutes and have vetted pros onsite before the paint dries.

Quality hasn’t drowned in quantity. The firm consistently earns “Best of Staffing” honors for client satisfaction, and Reddit threads packed with assistants confirm the praise. One EA noted that her Beacon Hill recruiter “followed through every step and placed me, plus two admins at my current company.”

On the employer side, clients appreciate the two-tier vetting model. Local recruiters conduct behavioral interviews, then a centralized compliance team handles background and reference checks. The result is a shortlist that’s both quick and clean.

Flexibility is Beacon Hill’s ace card. The company supplies day-rate temps, six-month contracts, or retained searches for Chiefs of Staff under one roof. If your HR team juggles multiple staffing categories, consolidating with Beacon Hill can cut paperwork and speed approvals.

For executives who want enterprise-level bandwidth without losing the personal touch, Beacon Hill offers the best of both worlds: national muscle, local heart.

6. Career Group: coast-to-coast polish, Midwest presence

Career Group cut its teeth staffing power assistants in Los Angeles boardrooms back in the early eighties. Four decades later, its Chicago office imports that Hollywood-grade polish to the Midwest.

The firm’s calling card is white-glove service for both sides of the desk. Recruiters dig into an executive’s work style—hands-on versus hands-off and rapid-fire Slack pings versus neatly batched check-ins—then mirror those preferences when sourcing candidates. The goal is chemistry you can feel by the second Zoom call, not just a résumé match.

Reputation travels. Forbes has listed Career Group among America’s Best Recruiting Firms multiple years running, and that brand cachet attracts high-caliber, often passive, talent. It’s common for their pipeline to feature senior EAs who have supported studio chiefs, hedge-fund founders, or Silicon Valley unicorn CEOs, professionals who seldom post on public job boards.

Flexibility is solid. The company offers temp, temp-to-hire, and direct-hire options, but where they excel is placing long-term executive support in high-expectation environments: private-equity partners, family offices, global marketing agencies.

Candidate feedback is mostly glowing, though experiences can vary by individual recruiter. The best advisers here act like career agents, editing your story, prepping you for C-suite panel interviews, and coaching salary negotiations so you don’t leave money on the table.

Choose Career Group when you want a recruiter with nationwide reach, meticulous presentation standards, and a knack for courting top-tier assistants who expect red-carpet treatment and then deliver it to your leadership team.

7. Steele Recruiting: concierge search for elite EA and chief-of-staff roles

Some executive hires require total discretion and an eye for the extraordinary. That’s the lane Steele Recruiting owns.

Founded in 2018 by Diane Steele, this WBENC-certified boutique places only Executive Assistants, Personal Assistants, and Chiefs of Staff. The focused model means each recruiter spends every hour networking with top-tier support talent rather than juggling unrelated disciplines.

The process feels more personal than transactional. Steele begins with a deep-dive intake that clarifies your executive’s quirks, preferred travel vendors, communication cadences—even how they like coffee staged for a 7 am board call. Armed with that detail, the team headhunts passive candidates, many referred by Fortune 100 assistants they placed years earlier.

Because the firm often manages confidential replacements, recruiters arrange off-site or after-hours interviews and handle NDAs as a matter of course. Clients cite that privacy as the reason they return when they need a Chief of Staff to manage family-office investments or an EA who can double as event producer.

Candidates benefit as well. Reviews highlight concierge-level prep: résumé tailoring, salary benchmarking, and honest feedback even when a role isn’t the right fit. That respect cements long-term relationships, so when a standout role surfaces, Steele can tap a roster of ready, vetted professionals.

Choose Steele Recruiting when the assignment is sensitive, the bar is high, and “good enough” won’t cut it. The team will deliver a short list equal to the challenge.

Quick-scan comparison matrix

We just covered a lot of ground. If you’re skimming between meetings, the table below distills the essentials, helping you match an agency’s strengths to your need in seconds.

Agency	Chicago tenure	Core specialty	Best public rating*	Temp-to-hire?	Sweet-spot searches
C-Suite Assistants	15+ yrs serving local C-suites	EA & PA only	High (client repeat rate)	Limited	Confidential C-level support, Chiefs of Staff
City Staffing	33 yrs	Office & EA, temp + perm	4.8★ client & talent, 2026 Best of Staffing (clearlyrated.com)	Yes	Rapid temp cover, direct-hire EAs
Mack & Associates	39 yrs	Admin & EA perm + temp-to-hire	4.9★ client (600+ surveys)	Yes	Culture-fit long-term EAs
The Larko Group	30 yrs	Admin/EA temp & perm	4.7★ avg. online reviews	Yes	Fast turnaround interim EAs
Beacon Hill (Assoc.)	15+ yrs	Broad admin staffing	4.7★ client satisfaction	Yes	Multi-role or high-volume EA teams
Career Group	20+ yrs	EA & admin across industries	Forbes “Best Recruiting Firms”	Yes	High-touch permanent EA roles
Steele Recruiting	National reach (HQ in MN)	EA & Chief of Staff only	4.7★ agency rating	No (perm search)	Ultra-select C-suite matches

*Best publicly available metric as of July 2026. Sources include ClearlyRated, client surveys, Forbes lists, and verified online reviews.

Use this grid as a launchpad, then circle back to the detailed write-ups when a name catches your eye.

How to choose the right executive-assistant recruiting partner

Seven strong agencies still leave you with a decision. The best fit depends less on marketing copy and more on your own priorities: timeline, budget, culture, and risk tolerance.

Start with communication. Great recruiters stay visible from first intake to final offer. In a June 2026 Reddit thread, one EA vented about “seven recruiters who enticed me with a job and then disappeared,” while another praised a Beacon Hill rep for staying engaged at every step. Ghosting wastes everyone’s time, so measure responsiveness in the first 48 hours.

Next, match specialization to role complexity. If you’re hiring a Chief of Staff or a hybrid EA/PA, boutiques such as C-Suite Assistants or Steele Recruiting deliver focused expertise. For high-volume admin needs or rapid temp cover, City Staffing or Beacon Hill’s Associates division offers bench strength.

Budget counts, but fees are largely uniform. Most firms charge 20 to 25 percent of first-year salary on a contingency basis, payable only when you hire. Ask about guarantee periods; 90 days is common and protects you if the match fizzles early.

Speed versus precision is the classic trade-off. Agencies with triple-digit candidate pools can present résumés tomorrow, yet a concierge search that takes six weeks may spare you from a bad cultural fit. Decide which outcome matters more right now.

Finally, trust your intuition during the kickoff call. Does the recruiter ask sharp, challenging questions, or simply nod and promise miracles? A partner who pushes for clarity today will save you headaches when the assistant is booking a 6 am flight tomorrow.

Treat the selection like any other executive decision: align on goals, test for competence, and hold people accountable. Do that and whichever firm you choose will feel less like a vendor and more like an extension of your leadership team.

Chicago EA salary snapshot, 2026

Money sets expectations on both sides of the desk, so let’s anchor the conversation with fresh numbers.

Indeed’s June 2026 data puts the average base salary for an Executive Assistant in Chicago at about $84,000. Human-resources and staffing companies top the charts at roughly $101,000, while finance, consulting, and legal roles hover in the mid-$90s range.

What pushes an offer higher? Three factors show up consistently.

First, sector intensity. Private-equity and trading firms routinely cross the $100,000 mark, adding bonuses that push total compensation well into six figures.

Second, scope creep. Hybrid EA/Project-Manager or EA/Chief-of-Staff titles attract a premium, sometimes ten to fifteen percent, because the assistant is expected to handle budgets and lead workstreams, not just calendars.

Third, flexibility. Roles that promise two remote days or offer professional-development stipends close faster even at the same salary. In a tight market, perks convert fence-sitters.

At the other end of the scale, nonprofits and higher-ed still advertise ranges in the low-to-mid-$60s. A recent Fishbowl screenshot of a consulting firm dangling $65,000–$75,000 for a “high-level EA” drew instant scorn, proving that experienced assistants know their worth.

Rule of thumb: set a floor of $80,000 for an on-site, mid-senior EA; budget $90,000–$110,000 for elite C-suite support; and sweeten the pot with reachable bonuses or hybrid days if you want your hire to stay.