Home insurance in Chicago is a masonry and wind conversation held against your own policy. Rain through a failed parapet is not the same claim as a sewer at the floor drain. Your deductible for wind may not match the deductible for everything else, and only the page you hold can say. Bring that page. A two-flat and a bungalow do not present the same dwelling, even when they share a block.
A ponding roof can open a seam in one storm and look like years of neglect. Ask how your policy treats sudden water from above versus a long-term maintenance argument. Describe what the last storm changed, not the whole history of the wall. Interior stains, ceiling collapse, and lost use of a unit are the facts. Photos of the coping and the top-floor ceiling belong with the claim.
Dwelling limits on older Chicago buildings are where arguments start. Brick, plaster, and custom millwork do not rebuild on a purchase-figure habit. Ask whether your limit tracks a rebuild or tracks what you paid. If two units are in play, say which loss is yours, because structure and belongings are separate lines. Loss of use only helps if the policy says a covered loss made the place unfit.
Basement water needs plain words. A floor drain, a window well, and a failed drain tile are different paths on a policy. Sewer backup is a specific question. Flood is often not the homeowners policy at all. Do not let a neighbor's story decide which one you have. If a claim is already open, have the claim details in front of you and lead with that.
Chicago lake wind will keep testing copings and old roofs. Have your deductible, your policy, and the path the water took. A two-flat claim is clearer if you name the floor. Photograph the parapet before anyone patches the ceiling. Say masonry if the wall is the opening. Call the number on this page.