Diaryland insurance. Dairyland Insurance, headquartered in Wisconsin, provides car insurance coverage across the United States, in all 50 states. This insurer is known for its focus on high-risk drivers, offering them coverage options when they may have difficulty securing insurance elsewhere. This review will provide a balanced look at Dairyland's services ...Sep 28, 2023 ... Dairyland auto insurance costs around $237/mo. Read our Dairyland auto insurance review to compare SR-22 coverage, rates, and customer ...Progressive. $256. $180. Looking at the national average rates for both companies, Dairyland is quite a bit more expensive than Progressive, with premiums averaging $256 per month compared to just $180 with Progressive. Even so, that doesn't mean Progressive will necessarily be more affordable than Dairyland for every driver. 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