For flights, your first stop can be matrix.itasoftware.com -- play with the "Nearby" city option, and the "Calendar of Lowest Fares" function, to identify fares that are unually low, if your cities and dates are flexible. Once you find the low fares, you can learn fare rules and decide how to maximize mileage, then choose the frequent flyer account that will earn a bonus (like, some routes may give double miles) or push you toward elite status. Elite Status comes with an automatic mileage bonus-- earning 50% more miles is comparable to earning an extra cash return on your investment.

Don't be married to ITA searches only, though-- keep your eyes open for changes in the industry. Airlines like Allegiant and Spirit will offer ultra low fares on many of their routes, so if you learn where they fly, you'll know which specific routes to watch. The airlines and routes that work will be determined by where you live-- and where you choose to go to school.

Finally, periodically check Megabus.com since they will deliver you from Kansas City to St Louis or Chicago, and offer leverage to use the Nearby City fares you find on ITA.

Developing your skills is a work in progress, but I think you've found answers to your question of "where do you start."