Proximity is the constraint nobody wants to hear
Local map results weight how close the business is to the searcher heavily. A single location in Rogers Park will struggle to appear for searches on the far South Side no matter how good the site is.
The honest strategies are to dominate the radius you have, add legitimate locations if the business supports them, and win organic results for area searches where proximity carries less weight.
The long tail is where the margin is
Head terms in Chicago carry the highest competition and the lowest intent clarity. Neighborhood and job-specific searches carry less volume each but far better conversion, and they add up to more total work.
Twenty pages that each win a specific search beat one page that comes eleventh for the phrase everyone is fighting over.
Timelines here are longer, and pretending otherwise wastes a year
In a low-competition market a well-built page can rank in weeks. In Chicago, against competitors with a decade of links and thousands of reviews, three to six months to a stable position is the realistic range.
Anyone promising a top-three head term position in sixty days here is selling a timeline that the market does not support.