Quick answer: You are within guidelines The longer answer is both a carseat and a stroller may be checked for free in addition to your 2 free bags. In other words, you could actually check an additional bag for free. Maybe check the one you were planning on carrying on so you are carrying less? Gotta love Southwest and free bags! Your plan looks great, and thank you for taking the time to detail it out! Here's the actual policy regarding the stroller and car seat: https://www.southwest.com/html/customer-service/baggage/carryon-bags-pol.html "Customers traveling with children will be allowed to check one stroller and one Child Restraint System (CRS) or car seat per child without charge. This is in addition to the regular free baggage allowance." --TheMiddleSeat
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