If the dr visits were b/c of a car accident, you can use your PIP, personal injury protection, part of your insurance to pay all or part of the medical bills. Most insurance policies come with $2500 coverage. Using this coverage will not increase your premiums, so give that information to your dr's office for them to get paid. Then I would call a lawyer and find out what can be done with the rest of the situation.

Good Luck!!

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Who Is The Best Toronto Criminal Defence Lawyer?

You can file a case but before that consult some attorneys for the procedure on how to handle this matter. Refer this website for some basic information that you need on how to file the claim.
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You need to speak to an attorney. They will be able to answer all your questions and help you decide if filing a lawsuit against the city is the answer. Consultations are usually free. If you decide to move forward with a lawsuit and are struggling to pay off your medical bills, lawsuit funding would be a good option for you. It can get you money from you settlement now, when you need it. Orchard Legal Funding is company that handles cases like yours.