Chicago has a tradition of poor leadership at the mayoral level. Both Mayor Daleys did some good things - but left the city in poor financial shape. Rahm did a reasonably decent job of improving the image of the city, focused on tech and education - and made some hard calls to address the financial situation in the city - but the city is still struggling in that area. Daley's giving away the parking meter business really f'd the city long-term, a legacy that perhaps no one can fix. He's smart, tough, articulate, disciplined, strategic -but I'm not sure how well he does with unifying as suggested by Bernard - some parts of the coalition might not show up for him.
One thing that would be interesting is he has no love for Netanyahu - that could be a deal breaker or maker for some.

