Back in 2009, Southwest introduced the concept of “Early Bird Check-In” where Southwest would automatically check you into your flight prior to the 24 hour check-in mark. While this comes with a fee, it theoretically gets you a better boarding position. With Southwest, you do not pick a seat upon booking your flight, instead you receive a boarding position and your seat is based on a “first come, first serve” basis. The better your boarding position, the more options you have to pick your seat upon boarding the plane.
When it was first introduced, it cost $10 per ticket. It then went up to $15 a ticket. And now, starting on August 29th, will cost anywhere between $15 and $25 a ticket. The price for Early Bird Check-In will be based on the length of the flight and the typical demand of Early Bird check-in on that flight. The good news though is if you have a flight post August 29th, as long as you purchase the Early Bird Check-In option prior to this date, you’ll still be locked in at the $15 per ticket price. 
I am actually NOT a fan of Early Bird Check-In regardless of price. I am a huge Southwest flier. For the past 10 years it has actually been my airline of choice. I have been a Southwest Companion Pass holder all of this time and fly Southwest a ton. I fly by myself, with my husband, and with my kids. And I have not once paid for Early Bird Check-In! When I travel with my kids, I am always allowed to board between the A and B group, so I have never had a problem with getting us 4 seats together. And when I am traveling with myself or my husband, I just make sure to check in exactly 24 hours prior to my flight! I actually just checked in for two different flights within the past few days and received B14 on the outbound and A40 on the return. With those numbers, you can always snag a window or aisle seat and will not have to be stuck in the middle. Of course if you need one of the first few rows of the plane or an exit row seat then those boarding numbers probably won’t work for you.
I try to travel as low cost as possible, so for me, the extra expense has never been worth it. But I definitely understand that there are many that prefer this option. For those that enjoy Early Bird Check-In, this could mean an extra $20 out of pocket for a roundtrip flight and let’s say you are flying with a family of 4, that’s another $80 total! This is definitely a huge price increase and might make people think twice before purchasing it.
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I like the Early Bird option for when we are flying on ski trips. We could be out on the slopes and it can be difficult to time (and sometimes difficult to get a good internet connection at 10k feet!) the 24 hour check in. For the extra money at least I know we are checked in and have the best possible boarding position.