Right now for October, Southwest is showing anywhere from about $240 to $332 (before taxes) per person round trip as lowest fare for non-stop flight with the variance depending on day of the week and time of day you go and come back. Sometimes those lowest fares go quickly but other times those lowest fares may even get lower as you get closer to trip time. The thing with Southwest is that you can book at a higher fare and then change later to a lower fare if one appears (by cancelling and rebooking) without paying any extra fee to do so. However, you don't get the saved money back. Instead, you can use it on a future flight but must use it within a year from when you initially booked or lose it.
As noted, there is no seat assignement and if you want to be in the "A" boarding group (first ones to get on after those with special needs; they have A, B and C groups with C being the last to board and likely to get only middle seats) you need to go into the website 24 hours before the flight and get boarding passes (and you have to do that for going and then separately for coming back). You can't do it before 24 hours beforehand and if you wait until 23 1/2 hours beforehand all the "A" passes are likely to be gone; in other words you have a very small window to get an A pass.
There is a way to guarantee an "A" ticket -- you can after you book or as you get closer to that 24 hour period pay an extra $10 per ticket ($20 person round trip) to get an "EarlyBird" check-in (it is also on-line) which then automatically gets you an "A" ticket when the 24 hour check-in period begins and you don't have to worry about checking in exactly 24 hours beforehand.
We now always fly Southwest from Chicago Midway to Orlando because (a) the fares are usually better than others (but that is definitely not always true); (b) flights are seldom delayed -- my long-time experience at O'Hare with companies like United and American is that delays are the norm (and contrary to the above you are about 10 times more likely to get a flight cancelled at O'Hare than Midway); (c) you get more leg room between seats-- the other airlines have in the last 15 years basically shrunk the distance between seats in coach to nothing (Southwest has only coach); and (d) Southwest doesn't charge you for bags as long as it is no more than 2 a person (something you need to factor in when comparing prices with others, e.g., United is now $25 for the first bag person and $35 for the second each way, meaning when comparing prices for the flights you need to add at least $50 a person to any round-trip fare listed by United if you are going to check a bag per person)
Thanks in advance for any experience you can share.
