This week's cover story | The Deals Issue

Here's a sneak peek at what's coming up in this week's Time Out Chicago, on newsstands tomorrow:

There are some of us (my mother) who, when given a choice between two similar items, will always choose the cheapest one. No matter if the cheaper one is made of the chintziest material this side of Bangladesh and will fall apart after a few wears, the cheap one is a deal. Sometimes, my mom is right: Who needs high-quality purple jeans when that color will be out of style next season? But when it comes to things like bikini waxes and fresh produce, it pays to shell out more.

In this week's Deals Issue, we help you through that difficult choice—cheap out or pay up?—by weighing all the important factors such as how much of a hassle the cheaper item is, whether the more expensive choice will pay off in the long run and more. Turns out, more often than not, my mom is right. As if there were any other option.