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Factors -

Job stability
Firm culture (everyone I met at both firms was really great; by culture I mean more whether a person can expect to work from home on weekends, do people have social lives outside the firm, etc... And does Winston deserve its "stodgy" reputation? How badly did the stealth layoffs really hit morale at Latham?)
Advancement opportunities
Opportunities for meaningful work
Exit options if one goes in that direction

-Prestige is only important to me as it relates to the above factors.
-My interest is litigation.
-I plan to stay in Chicago indefinitely.

Thanks!

I know a number of attorneys at Chicago firms who had left Winston. All of them (independently) strongly advised me to avoid Winston. They reported a terrible firm culture, closed doors, lack of transparency in any firm decision making etc.

That being said the firm didn't seem terrible in my interview experience. I liked Latham more, but I'm curious to hear what other people think about Latham Chicago

Know tons of Latham attorneys in Chicago who have left or are trying to leave. Also, check out how much Latham has shrunk in the past 5 years (immensely). Furthermore, Chambers ranks Winston HIGHER than Latham in every single group in Chicago except for Corporate. When it comes to Latham/Skadden in Chicago, their biggest strengths are M&A. Winston for sure.

OP here - thanks. The votes seem pretty heavily skewed towards Latham - any comments as to why? I'm going on follow up visits to both, but there's only so much you can learn from an associate who is actually working there, I think...

The votes are heavily skewed towards Latham probably because most people voting are not actually knowledgeable about Chicago. Latham is better nationally, so people just pick it. Winston is infinitely the better choice in Chicago.