Zillow Rental Manager has by far been the most productive platform for me for the last few years. I've had some success with Apartments.com and FB Marketplace, but less consistently.
If a listing goes more than a couple days without a nibble, I know I've probably overpriced it. I've always found it helpful to go to the map view of listings in my area to see what potential tenants might be comparing my listing to. Hotpads (where Zillow Rental Manager automatically cross-posts) is especially good for this because you can see how many people viewed and contacted each listing. Look at the popular listings to see how they're priced, shot and described. You might get some ideas for how to refine yours.
Renting in the middle of a Chicago winter is tough...I've been there. When you do find a tenant, see if they'll sign a lease that ends in the May-September range so you can get on a better leasing schedule. Best of luck!