Where can I get earlobe piercing repair for an average of $300 (or less) per ear in Chicago? (Photo)

Thanks for the question. You will find many qualified plastic surgeons in your area. When it comes to costs of surgery, there may be many “variables” involved. The specific surgeon's credentials/experience level (or lack thereof), the specific geographic area you are looking at, the different operations available, the location of the procedure (quality of surgery facility)… are some of the potential variables involved. You will find some average costs of surgery on this website and on individual plastic surgeons' websites as well.
In regards to outcome of the planned procedure, more important than costs of the procedures will be careful selection of your plastic surgeon. I would suggest starting with the American Society of Plastic Surgery and/or the Aesthetic Society of Plastic Surgery to obtain a list of well experienced board-certified plastic surgeons.
Then, I would suggest you visit a few surgeons whose practices concentrate on aesthetic surgery. Ask to SEE lots of examples of their work AND preferably speak/see patients who have had similar procedures done.
Be very careful with your decision-making. You will find, while doing your due diligence, that there are many different “specialties” who will offer their services to you; again, I strongly recommend you concentrate on surgeons certified by the American Board of Plastic Surgery.  I would also suggest that you do not base your selection of plastic surgeon primarily on costs of surgery; keep in mind that revisionary surgery may be more costly in many ways. I hope this, and the attached link, helps. Best wishes.