Most likely. Go on the SW website and check it out for sure (when you're looking, you can change from dollars to points). Also look at other dates (there's a way it'll show you a calendar view with the cheapest fares for every day).
You don't say for how many people or when though which will make a big difference. My son and I each took 2 RT flights plus had some leftover but I still move dates around for the best price (which i thought I wouldn't do when using points, but I was wrong).
Usually the average is 17,000-24,000 points (total) per RT flight from what I have seen from Chicago to Orlando. Last fall my family of 7 flew from Chicago to Orlando via SW. I had 50,000 points from the CC and my husband had 50,000 points as well. We were able to use points for 6.5 of us. We had to purchase a one way flight to complete the airfare for our family.
Right now there are lots of one-ways at 7683 pts. Some are even nonstops! That's a pretty good price. I looked at June and September. So a round trip is 15,366 pts for each person. These things change every day, but at least that tells you it is possible to get 3 round trips, if you can catch those lower fares.
I have to say I am jealous of all the time choices and nonstops out of places like Chicago!
You all are right. 50,000 would be enough. Too bad I missed that promo and it's down to 25,000 points! That is enough for 1 round trip, but we need 2 and it makes more sense to use my other reward cards instead of opening a new one if we can't get 2 round trips.
You should. We were able to get ours on sale and out of 8 one way got 6 of them. The great thing about the points is that if the tickets go on sale you can change them and the points will go back in your account.