FlyerTalk Forums - Is 55 min layover long enough at MDW?

Hi everyone, I'll be traveling to Disneyland in November with my family (2 adults, 1 child who is 5). We will be booking flights this week, and it looks like flying Southwest PHL to LGB is our best bet for times/prices. However, I've never flown through MDW and I'm not sure if a 55-minute layover is enough. I tried searching, but didn't see much other than some very old threads.

We would be flying out Nov 13th, and it would all be booked roundtrip, PHL to LGB, through Southwest. The issue is, the only real options we have are:
1. a 55-min layover at MDW -- it does involve changing planes, but is an early flight, departing PHL at 7:50am and arriving at MDW at 9am. From there, our connecting flight would be leaving at 9:55am to arrive in LGB at 12:30pm.
2. layovers of ~3.5 hours in St. Louis -- departs PHL at 8:15am, arrives STL at 9:45am, and departs STL at 1:40pm. This gives plenty of time, but I'm not sure that an almost 4-hour layover is going to be great with a young child :D she was totally fine in the airport and flying LGA to MCO however, so I'm not 100% against it if that is the better/safer option.

Mostly, I'm just worried about weather-related delays. It looks like there are plenty of SW flights out of MDW after our connecting flight, but I also know getting on the next one is not guaranteed. For those of you more familiar with MDW, would the 55-min. layover be adequate or would you just take a 3-4 hour layover instead? Thank you!