I would not count on any "sale" fares during Spring Break. Many of the Southwest flights between MKE and MCO over those weeks already are sold out of the lowest fare type, Wanna Get Away fare. There are a few days where off-peak flight times, arriving in Orlando after midnight, are in the low hundreds today. The desirable flights usually get snapped up the very moment the flights are released for booking, with customers sitting at their computers, refreshing the screen, so that they can be among the first to book and grab a low fare. People often complain that they could not book till the day after schedule release, and by then, their first choices were either sold out or only flights with very high fares were still available.
Sometimes, you can find a lower fare flying out of Chicago Midway on Southwest. Or, your other nonstop option out of Milwaukee is Frontier, which gets mixed reviews. Frontier charges for checked bags, carry-ons (other than a small bag that fits under the seat in front of you), advance seat assignment, refreshments, all beverages, etc.; if you need to change or cancel, there will be a sizeable fee. It looks like Frontier's fares are not much better than Southwest's, during that time period.
If you absolutely need flights on specific dates over Spring Break, I would not wait any longer. to book Should your booked flights go down in cost, after purchasing tickets, Southwest will allow you to re-book at the lower fare, banking your savings in the form of a credit that must be used by the ticketed passenger, within one year from date of original purchase; travel must be completed by that one year anniversary.
With planes flying full on a regular basis, and especially over holidays, there is no need to offer a "sale," when there are not may unsold seats to sell.
