We've been watching for months!
We are flying down 10/17ish -10/26. Our DVC stay starts on 10/18 but since we are planning to fly out of GRR, we typically get shafted by SWA. There are no longer any non-stops and flights rarely arrive much before 3pm, unless we want to pay an arm and a leg. To add insult to injury, there are layovers of 3 hours or 2 stops involved so a lot of the itineraries are 5+ hours. There are 8 of us flying and we are hoping to get all of the flights with points since we have about 190K between the 8 of us. Right now, 5 people in the group are hoping to leave on the morning of the 17th, as early as possible. Me and my kids have to leave after school so we cannot leave on a flight that departs before 5pm. Fortunately, based on September's schedule, there are 2 flights that depart after 5, but only one of them would fit in our budget.
We are all returning on Saturday the 26th and we are going to book the latest, cheapest flight possible. When we look at September, there are 3 flights that all land in GRR at 10pm after connecting in MDW. They depart at various times from MCO at various prices with differing layovers. While we would obviously prefer the latest departure (5pm), it is actually the most expensive with only a 1-hr layover. We would actually opt for the middle one (a 4pm departure) with a 2-hr layover because it is much cheaper and it still arrives home at the same time. We are just hoping for something that we can afford that departs after 3pm because we are hoping to do a getaway day breakfast at Olivia's and we are staying at BWV. We don't want to get up too early, we don't want to feel rushed, and we want to leave plenty of time for transportation. We plan to use Uber so no worry about buses, but we still don't want to have a 10-11am DME pick-up time.