@fungible wrote: Hello, I'm trying to fly from BOS to LAX. I found a flight with a connection in MDW, but I discovered that it is actually cheaper to book the two segments (BOS-MDW and MDW-LAX) separately. I'm wondering if there is any risk in booking these two flights under a multi-city itinerary? For example, in the past, when I had a flight with connections and one of the flight segments was delayed or cancelled, I was able to be rebooked on another flight to my destination for free. If a cancellation or delay happens, would I not be able to be rerouted for free under the multi-city booking? I'm speculating a little bit, in combination with @bec102896's reply - Southwest won't want you to assemble a multiple city path when a packaged option is available. Them having a four-hour restriction migth accomplish a couple of things: Keeps people from optimizaing a few bucks on multiple one-ways where a published connection exists. Protects the flyer by providing re-booking for irregular operations where the separate one-ways might be re-booked with discretion of the gate agent, but don't seem to be obligated to be rebooked. Protects flyers that don't realize they may need to re-check baggage etc. - for a saavy flyer it might be fine, but they don't want people to accidentally do this and have a problem on the day of travel that could have been prevented. So anyway for your question - how much does it save, and I expect that it isn't using exactly the same flights as the published connection? I don't think this is worth it over less then $50 personally unless you plan to actually do something in Chicago for a few hours - the risk of a flight schedule hiccup becomes yours to some degree instead of Southwest's. (Especially at Midway, depending when the trip is weather could be a risk.)
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