In Chicago’s competitive legal market, prestige, compensation, culture, and opportunity all factor into how lawyers judge a firm’s value. A recent survey of midlevel BigLaw associates sheds light on which firm downtown is widely considered “the best.” The responses reveal that the top pick isn’t just the one with the most name recognition—it’s the one that balances the toughest demands with fair treatment, good pay, and realistic expectations.
What Associates Value
For midlevel associates—typically fifth to eighth year lawyers—the “best firm” moniker means more than just a lofty reputation. The survey asked what matters most, and here are recurring themes:
- Compensation and bonuses that reflect the work put in
- Associate expectations (hours, billable target, degree of oversight)
- Culture: collegiality, mentorship, and whether leadership is approachable
- Work-life balance, or at least respect for life outside of firm demands
- Opportunities for substantive work rather than just grunt tasks
The Winner: Kirkland & Ellis
According to the midlevel associate feedback, Kirkland & Ellis emerges as the firm most often named “best” in Chicago. Several factors drive this high ranking:
- Financial Performance
- Kirkland & Ellis is not only one of the largest firms in Chicago but one of the highest earners globally. Its profits per equity partner (PEP) routinely place it among the top law firms in the U.S.
- High revenue translates into generous associate salaries, robust bonus structures, and more resources for associates.
- Challenging, High-Level Work
- Associates point out that at Kirkland, even at midlevel, they are often entrusted with complex, meaningful work. Whether litigation, restructuring, or corporate deals, there is active involvement.
- That said, high expectations are a given—long hours and intensity are part of the package.
- Firm Reputation and Prestige
- As one of the firms most frequently ranked at or near the top in Chambers, Vault, and other rankings, Kirkland’s cachet helps associates in future career moves.
- Support and Firm Culture
- While the workload is heavy, Kirkland is lauded for offering structured feedback, mentorship, and leadership that is accessible.
- Associates also note the firm is better than many in offering flexibility when possible, and recognizing that people do have lives outside work.
How It Compares with Other BigLaw Firms
Although Kirkland got the most praise, it’s not alone in being highly regarded. Other Chicago firms also consistently measure up well:
- Sidley Austin: Massive global presence, big deal flow, solid compensation, and good reputation. Many midlevels appreciate the exposure to high-stakes work.
- Mayer Brown: Strong historical roots in Chicago, wide-ranging practice areas, and infrastructure to support large litigation and transactional practices.
- Winston & Strawn, Baker McKenzie, and others also get mentions in rankings focused on associate satisfaction, diversity, leadership, and work/life balance.
These firms have differing strengths—some offer more predictable hours, some more global exposure, some better work-life tradeoffs—but they often don’t win as many midlevel associate votes in terms of the overall “best balance.”
Trade-Offs That Associates Acknowledge
Even for the firm labeled “the best,” there are trade-offs. Here’s what midlevel associates say:
- Hours are intense. Expect commitment. Long days, traveling, and weekend work are often the norm. The “prestige” comes at a price.
- Burnout risk is real. Some associates say that despite the support, the accumulation of pressure over years can take a toll.
- Mentorship isn’t uniform. While many partners are praised for being engaged, experience can vary depending on practice group or specific leadership.
- Lifestyle is affected. While some firms are better than others in offering flexibility, the expectation of being “on-call” or ready often stretches beyond standard working hours.
Why This Ranking Matters
The insight from midlevel associates is especially useful because these lawyers:
- Are deeply familiar with firm operations—not outsiders, but people who’ve been through several years of the rigors.
- Are in a phase where upward mobility, meaningful work, and compensation are all in tension with personal life considerations. Their perspective tends to highlight where firms succeed—or fall short—in balancing ambition and human costs.
Bottom Line
If you’re a midlevel associate in Chicago looking for a BigLaw firm that gives you high-level work and treats you as more than just a cog in the machine, Kirkland & Ellis appears as the standout. It doesn’t sacrifice prestige or earning potential—but it pairs those with more of the intangible but deeply important things: mentorship, realistic expectations, and some respect for life outside the firm.
That said, “best” will always depend on your priorities. If you value the global platform, steadier hours, or a specific practice area, firms like Sidley, Mayer Brown, Winston, etc., might rank higher for you personally. But when the surveys speak—and midlevel associates do—Kirkland & Ellis takes the crown in Chicago.
