Hey everyone, just found this site, wish I knew about it earlier, and I’ve looked around to find the proper forum for this question, so if this isn’t the right please move.

Not quite sure how to ask this question, so I’ll put it like this: I usually fly Delta when I travel and will plan my trip according to when I want to leave and when I want to arrive at my destination. I almost never fly non-stop (I enjoy getting off the plane and stretching the legs), so when it comes to layovers I try to plan the flights in such a way that I have enough time to transfer planes, and if it’s around lunch or dinner time, enough time to grab a bite to eat. Some people don’t like a long layover and will choose flights and connecting flights accordingly, the key word being ‘choose.’ Next month my wife and I will be taking our daughter, who’ll be 11 months old at the time of the trip, to visit my family in New Mexico. This will be our first time flying with a baby and our first time flying Southwest in years. Normally I have no problem making quick connecting flights, but Southwest doesn’t really give you any options for picking and choosing connecting flights. My wife and I have ran through an airport before to catch an international flight in 10 minutes, so we can do that with no problem, but this time we’ll have a baby with us and only 40 minutes (that’s if everything is on-time) to make our next flight. We’re flying from Boston to Chicago Midway, change planes and then on to Albuquerque. Now, since Southwest picks your connecting flights for you, are they good about trying to keeping connecting flights fairly close together? I know, Southwest is an airline and can’t please everyone, and I understand that, but I was kind of hoping to taking a shot in the dark to see what happens. I guess I’m nervous about taking my first trip with my baby daughter and I’m venting my nervousness. If anyone has any insights on this I’d appreciate hearing them. If not, thanks for allowing me to ramble on.
Happy travels.