Lackluster performance unless the property is in perfect showing condition, takes full use of online and print marketing and priced right on. I've actually seen some multiple offer situations recently for properties that were in great locations. It doesn't have to be priced low but it needs to be priced where comps are selling, so it's a good idea to get a CMA and figure that out.
If you're trying to test the market with a high price or are on the fence about whether or not to sell at this point, I'd stick around for another year and see what happens. Once you know what your property is worth, you'll be able to answer this question more easily.
That being said, this is the best time of the year to sell your home in Chicago, historically, so if you're in a position where you really want to move, this is the best time to get it on the market.