The things to undestand about such a feature is not only what does it cover and what the limiations are, but also what is the process for getting it to cover.

While I don't have any experience with THIS PARTICULAR credit card feature, in general, often such coverages with many cards (and it varies from card company to card company) sound better on paper than they may be in real life if you have to do lots of letters and phone calls over months to collect some paltry sum.

Also, compare when the card kicks in with when other coverages kick in. For example, if after a certain number of hours of delay the airline is responsible for putting you up for the night (tho whether that applies may vary depending on the cause of the delay, sometimes weather doesn't count), and the card only kicks in after that, it means you'll only be able to use the card in case where the airline refuses to cover you (say, because they claim the cause of the delay didn't qualify). So you need to think back on the specifics of the cases where you typically get stuck in Chicago to evaluate how many of those cases it might have helped. (And then check to make sure it doesn't have a "FF exempt" clause like "only one claim per year" or such!)