Packaging Services

I don't trust anyone to pack them but myself. There are a few places around that sell boxes. Uhaul has some good t ply boxes, and some of the better packing stores do too (not the UPS store). Buy Styrofoam insulation at hope depot for padding and cut it to size. If the speakers are big and heavy I would build a crate, or at least reinforce the box using 1/4" plywood.

Dimensions & weight of the speakers? I once bought a "dish-pack" box at U-haul for about $10; it would fit most speakers.

That is, except for large floor standers.....

Or, you could maybe have the local UPS store do it. I believe they charge a LOT, to have some 19 y.o. kid put 1 layer of bubble wrap over your 50 lb. item.....(true story).

Styrofoam is the best packing material bet, but first put the speakers in plastic bags. The foam should be layered so it is at least four inches thick on all sides and glued together so it does not move. Each speaker should be enveloped in Styrofoam and securely fastened with packing tape so nothing of the foam moves. After packing, double boxing is a must.

I refuse to ship floorstand speakers. Won't buy them either if shipping is required. It has cost me money and extended the selling time, but the hassle of damaged speakers isn't worth the risk. For example, the last large pair of speakers I sold, and I had the original packing material, went for 20% less than offers from people who wanted the speakers shipped. Worth it though.
Selling in Chicago you should try "local sale only" and see what happens.

I agree with Timrhu. I did ship some floorstanders with success but in their original boxes. It can be expensive to properly pack large speakers. Sometimes its worth it to take the loss and trade them to your dealer. I have a local packaging place but they're not good with audio gear. Even when I tell them the worth they don't get it. Maybe you can meet a buyer half way. Ive done that, say maybe ho to 200 miles. You don't want what was once your babies to get hurt.