Definitely check right now during the sale ending Friday - this is one of the bigger sales Southwest only runs a few times a year. Use the "Flexible Dates" feature (looks like a little calendar) to see all the fares every day in a month view to spot the lowest prices. I think $310 for 2 people roundtrip is probably unrealistic for the DAL to GRR route, though. The lowest I just spotted when a ran a quick search was $127 one way - the total for two people flying roundtrip would therefore be $508. But you never know and fares do change regularly so keep checking! Hope you get to take the trip and don't be anxious - flying with Southwest is so much fun and a great airline for a newbie!
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A car seat or CARES is not required - by either Southwest or the FAA - for a child of any age on a flight. Of course, the experts agree that those are safer choices than using just the safety belt for younger kids, but the choice is up to you. I've flown on Southwest in every kind of situation -- with just a CARES, with just a car seat, and sometimes with neither -- for my children as babies, toddlers, and young kids. Never have had a problem with any of these configurations. I will say from personal experience that a two year old often doesn't want to sit quietly in the regular safety belt and may try an escape act during times when the child must be seated. If you have a long taxi, it can be hard to keep a toddler seated and compliant with the rules. I personally found a CARES helped manage that challenge for us at that particular stage.
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