I'm looking to redeem my Southwest points for a flight to Chicago. It is less points for us to get tickets to Cleveland and then get off at Chicago where we switch planes. Our return flight would also be on Southwest but the departure city would be Detroit. My wife and I always carry-on except for gate checking a stroller and car seat. Booking the tickets to Cleveland would save us about 4,000 points, is it worth the risk especially since we will be flying southwest back home although from detroit.