High winds and driving rain in Chicago loosen shingles and lift flashing, so a fast post-storm inspection is the cheapest way to stop a small tear from becoming an attic leak.
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In Chicago, a roofer job driven by roof size, pitch, material, and storm damage generally runs $8,000–$25,000. This is a general range — always get itemized written quotes.
For a typical single-family home, most homeowners spend somewhere in the mid-five figures, but costs vary widely with roof size, pitch, material, and how much decking needs replacing. Get at least two itemized written quotes to compare.
Most residential asphalt-shingle replacements finish in one to three days, weather permitting. Larger homes, steep pitches, or tile and metal roofs can take longer.
Isolated damage on a roof under about 15 years old is usually worth repairing, while widespread wear or a roof near the end of its rated life is often cheaper to replace outright. A reputable roofer will show you photos rather than pressure you — costs vary, so get it in writing.