Used heels in Chicago typically sell for $16 to $81. Heels are judged on the parts that touch the ground, because worn tips and scuffed heels are the first things a buyer sees.
Selling heels in Chicago
Chicago has real winters and generous pre-war apartments, which is an unusual combination and it shapes what sells. Serious cold-weather clothing has a genuine local market, and the older buildings mean full-size furniture actually fits, unlike in the coastal cities.
Leases across much of the city turn over on common dates, which concentrates moving into a few weeks and floods the market at once. That is the best time to buy and the worst time to be selling something ordinary.
The L covers the city well and is how most small items move. For furniture, the alley behind the building is usually the practical loading point, and winter is a genuine obstacle — nobody wants to carry a couch through snow, so prices soften.
Anything stored in a garage or basement here has been through freeze-thaw cycles. Check for rust on metal and splitting on anything glued, and ask whether it was ever kept somewhere heated.
Handing it over in Chicago
Distances are the real constraint. State plainly whether you will ship or collection only, because a buyer three states away will otherwise ask.
What heels are worth
What lifts the price
- Recognised designer labels with a resale following
- Original box and dust bags
What pulls it down
- Scuffed heel stems and toe caps
- Very high heels, which suit fewer buyers
Working out what yours is worth
- Look at the heel tips and note whether they need replacing
- Photograph the soles and heel stems
Getting it ready
- Check every heel tip. Worn-through tips exposing metal are both a defect and a floor hazard, and replacing them is inexpensive.
- Inspect the heel covering for lifting or scuffing, which is the wear point on covered heels.
Photograph
- The soles and heel tips together
- The insole and inside label showing brand and size
Put in the description
- Heel height in centimetres, and heel type — stiletto, block, kitten or wedge
- Material of the upper and whether the sole is leather or synthetic
Post boxed, with each shoe wrapped and the heels protected. Thin heels snap in transit when they are loose in a padded bag, so a rigid box is worth the small extra postage.
Listing is free and there is no selling fee, so the whole amount the buyer pays stays with you. You and the buyer agree the handover between yourselves.
Same region (Illinois)
Common questions
Where can I sell heels in Chicago?
Put it on WishThrift free and deal with the buyer direct. The L covers the city well and is how most small items move. For furniture, the alley behind the building is usually the practical loading point, and winter is a genuine obstacle — nobody wants to carry a couch through snow, so prices soften.
Do they fit true to size?
Give the insole measurement heel to toe. Court shoes especially vary between brands, and a measurement is the only answer that works for everyone.
How much are heels worth in Chicago?
Most used heels change hands for $16 to $81. Condition and completeness move that figure more than anything else.
More: selling heels across the United States, what heels are worth, everything second hand in Chicago, or Shoes & Footwear in Chicago.
Guide range converted from sterling at the 2 August 2026 rate, not a quote — sellers set their own price.