Re do a chair idea! Need your help!
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I'd probably cut a piece of plywood to fit the chair seat right on top of what is already there. Upholster the new plywood and then place over the old seat.
Does it have to look like wicker? What about making seat cushions for the whole set?
I would cut plastic grocery bags into thin strips and weave over the broken area and then the entire seat( then paint of course). The plastic bags are weather friendly and strong. People have been using plastic bags to crochet and knit bags and they are very strong.
You could also spray paint the chairs to make them look nice again and make cushions using weatherproof fabric like folks mentioned above. Brylane Home also has very inexpensive patio cushions, $50 for four that you could purchase in quite a few different fabrics: http://www.brylanehome.com/decor/Set-of-4-Stacking-Chair-Pads-1Hx16Wx17and8539L.aspx?PfId=127496&DeptId=15568&ProductTypeId=1&PurchaseType=J&pref=npc&rec=Certona
You could paint these at, back & arms of the chair one color& the legs a contrasting color. Using a waterproof board (check at the lumberyard), cut to fit the seat, upholster in a fun outdoor fabric.