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Based on the most helpful WSO content, here's a breakdown of your options:

1. Lincoln International (Chicago):

• Culture: Lincoln is noted for its growing presence but has been mentioned on WSO for some negative reasons in the past. However, it is often regarded as a culture leader among the three, which could be a significant advantage if you're prioritizing fit and work-life balance.
• PE Placements: Lincoln has a solid reputation for middle-market deals, which can provide good exposure for private equity exits. However, it may not have the same level of prestige or network as some larger firms.
• Compensation: Specific comp details aren't provided, but as a middle-market firm, it should be competitive within the MM IB space.

2. Baird (Milwaukee):

• Culture: Baird is well-regarded for its strong culture and employee satisfaction. It’s often highlighted as a great place to work, especially for those who value a collaborative environment.
• PE Placements: Baird has a strong reputation in the middle market, and its analysts and associates often place well into private equity roles, particularly in the Midwest.
• Compensation: Competitive for middle-market investment banking, though Milwaukee’s lower cost of living can make the comp go further.

3. Houlihan Lokey (Minneapolis):

• Culture: HL is known for its strong restructuring practice, but in Minneapolis, the focus is likely more on middle-market M&A. The culture can vary by office, but HL generally has a reputation for being more intense compared to Baird or Lincoln.
• PE Placements: HL’s strong deal flow and brand name can provide excellent exit opportunities, including private equity. However, the Minneapolis office may not have the same level of prestige as HL’s larger offices.
• Compensation: HL typically offers competitive comp, and Minneapolis’ cost of living is also favorable.

Key Considerations:

• Location Preference: If Chicago is your top choice, Lincoln would be the most logical option. However, Baird in Milwaukee is a close second, especially if you value culture and are open to Milwaukee’s proximity to Chicago.
• PE Placement: All three firms provide solid middle-market PE exit opportunities, but HL’s broader brand recognition might give it a slight edge for national placements.
• Culture: Lincoln seems to lead in culture, followed by Baird. HL might be more intense, depending on the office.

If culture and Chicago are your priorities, Lincoln could be the best fit. However, if you’re open to Milwaukee, Baird offers a strong combination of culture and PE placement potential.

Sources: Top Industrials Shops in Chicago - Top IB Chicago, B Riley, Blair, Stifel, Baird, Lincoln - Any Insight?, bb chicago or mm chicago for IB?, Top Chicago IB, Top Chicago IB