As I travel back and forth to the Midwest 7-8 times a year, I've had to find the lowest possible fares.
I live near Indianapolis but the fares have gone to 600-700 dollars. So I fly out of Chicago. My highest fare is Delta $240 ORD. I booked sale flights on Southwest for $100 RT...It's $25.00 Shuttle, so $50.00. That's a total of $390. If I want to go cheaper, I take the train from Indy for $38.00RT and shuttle to ORD for $40.00 RT.
If I want to get real cheap, I hike .3 miles to the CTA and reduce my $40 to $5.00.
To chart the fares, I use Kayak and get daily alerts. The cheapest flights this time came 2 months before flight time, during a sale. In the past, it usually was a month beforehand. Since all Chicago flights connect, I've checked my flight dates from the connecting terminal to SJO and the segment is usually $200-$300 more than my Chicago departure. Go figure. I think the pricing is done the way derivatives were done in the 90's, by PhD matematicians.
I also get emails from
www.smartertravel.com, which alerts me to fare sales. That's when I check.
So far, only once have I not booked the cheapest online fare. I missed by $10.00.