Mileage Run Deals - Increasing mileage/segments Q

I've read through the posts and one thing is still unclear to me. How do you go about breaking up the flights to multiple segments outside of what the airline offers without ballooning the fare price? For example, Tuesday I'm traveling from ORD to MIA on business. I can book most any flight out of ORD but AA only shows up to 1 stop each way. Do you somehow pick certain stopover cities and then do a multi city booking?

Good question, I want to know what engines people use to find these deals.

I've read through the posts and one thing is still unclear to me. How do you go about breaking up the flights to multiple segments outside of what the airline offers without ballooning the fare price? For example, Tuesday I'm traveling from ORD to MIA on business. I can book most any flight out of ORD but AA only shows up to 1 stop each way. Do you somehow pick certain stopover cities and then do a multi city booking?

Best bet is to take the city pair you're looking for and fire it into http://matrix.itasoftware.com -- using the routing language explained in the sticky. Try as the From: "ORD::AA AA AA" to get three segments on AA, and repeat in the "to" field (e.g. if you're going to LAX, type "LAX::AA AA AA". If you want more segments, then try adding another "AA" - and stop where the price maximizes.

You can also look it up through http://www.expedia.ca - look at the "rules and regulations", where it will tell you the routing you can use as well as the maximum number of connections.

So then how do you normally go about booking the fare? The thing I found online is to use multicity leaving out the hubs. However, most booking sites don't allow for more than 4. Gotta use an agent?