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Unfortunately, your employer isn't liable for the costs of your family's trip or the extra nights. The firm is only responsible for the costs of travel (and the cost of cancelling reservations) that is directly related to your time at the conference, as directed by your manager.

However, you might consider having a discussion with your manager about your concern. He/she can advise you about options you have that are consistent with company policy and regulation and may be able to come up with a compromise solution that allows you to still go on the vacation.

Even if your company or manager wanted to be very generous and cover the cost of the cancellations for your family, the firm may not be able to easily do so (those costs are not business expenses and are instead compensation to you).

Take this experience as a lesson learned. In the future don't plan family vacations at work events. In this case the CEO canceled the event, but this is no different than if you had been laid off for whatever reason. While you were given assurances that the conference would happen, things changed and you should not assume that things will never change. Life happens both inside and outside of the company, you need to be prepared.

Maybe I could sue my employer? Maybe I should try to make an appeal to the CEO? Maybe I should just take my losses and start looking for a new job ASAP? Maybe some combination of the above?

Take your losses and learn your lesson, don't make the same mistake in the future and when doing any sort of travel consider travel insurance.

At companies where I've worked, development team members get a lot of leeway on schedule. HR rules like PTO are just a suggestion. The HR rules were only written so they could be used rigidly against people in less valuable positions/departments or against people who the company wants to get rid of. I'd go to your manager asap and tell him what you planned with your family and ask if you can work remotely from the conference town during the conference. Don't be afraid of asking because you don't get what you don't ask for. Oh, and make sure you do this in private behind closed doors.

I'm sorry to say this but you underestimated the risk you were taking.

This is somewhat similar to a situation where you book two separate flights to a destination: if anything happens to the first flight it's your problem if you miss the second one. Your employer arranged the conference and is responsible for the related bookings only. If they offered some sort of "bring your family along" or "conference + vacation" kind of option, they would also be responsible for the additional bookings for you your family. But I understand this is not the case: they merely allowed you to book your own ticket for a longer duration, and they already reimbursed you for that one. You booked the rest of the tickets yourself.

IANAL but I believe that suing for broken promises requires you to show damages resulting specifically from breaking the promise. If you cancel the bookings for your family, you will lose money because you cancelled them, not because the employer somehow prevented them from going. Also, "broken promises" are often dismissed if there was no consideration, that is, you didn't offer anything to your employer in exchange for the promise, so they didn't have to give it to you in the first place.

Travellers insurance comes in different kinds, and the most common kind covers your losses when you cannot (like when you're sick or your house just burned down), not when it's inconvenient. So it most likely wouldn't have helped. What would have helped is having refundable / flexible bookings.

Honestly, you need to have a sit down with your boss and see what they find reasonable.

The bare minimum I would accept are, any costs that were unavoidable by you. Such as reimbursement of your plane travel ticket. Plane tickets for family and a portion of accommodation costs do not fall into this category.

You should go into that meeting with a very detailed picture of how much money the cancelled plans have cost you. And be ready to accept that they may not offer you money to cover the entire amount.

You may want to ask for additional leave (either paid or unpaid) so you can make the most of the tickets already purchased. They may view this as an "easy" way to placate you. You could also suggest you work remotely, as @HenryM suggested.

In terms of suing the company, there is some sort of argument there. If they were malicious in their intent, it becomes a lot easier for you. But it would appear that it's just a shift in their business focus.

Also, suing the company is quite an aggressive action. It would be equivalent to a resignation letter.

I second sf02's answer, but I'd like to write a further note on that regard.

According to one of OP comments, it is not unusual for people in his company to merge business trips with personal trips, and indeed that might be a cost effective way of traveling with you family. It is not unethical of you to do it. But, you must also keep the company's priorities in mind. So...

First, keep in mind that the company can cancel any travel at any point in time. Doesn't matter how many times you are given "warranties" that this won't be the case, unforeseen events always happen. Some are unavoidable, like a snowstorm hitting the airport, and some might leave a sour taste, like the CEO of the company suddenly having crazy ideas.

To be at peace with the first point: Never plan a trip you can't afford yourself. Yes it is bad that you suddenly had a cost increase, but you need to keep the consequences of misfortune in check. If that cost increase implies you no longer have the funds to pay for the trip, then you shouldn't have planned it in the first place.

I would also not plan a trip in such conditions if business travels are rare. It is reasonable to assume that you'll be saving costs over time by doing this, but at any given trip, you are subject to the extra expenditures you are facing right now. So if you can rarely do it, you could hardly ever recover the loss of the one trip that didn't go as planned. Furthermore, if you are a frequent business traveler, you can expect to know and handle your company's travel policies very well, while that may not be the case when you rarely travel for work, or if the last time you did it was 2 years ago. For instance, do you know if your company always buys refundable plane tickets?

Likewise, how does PTO work in your company? Is there a formal agreement between you and the employer before these days off can be effectively taken off? Not sure about the US, but in most of the world vacations need to be scheduled in advance and cannot be suddenly and unilaterally postponed by either part.

All that being said, your boss should be a decent human, who is not willing to have a good employed pissed off. He could and should try to help you. Ask him for instance if there were company expenditures that are not reimbursable. Nonetheless, keep in mind that whatever help you get is from him trying to help/please you, as you are entitled to basically nothing in this scenario.

and he wants the development team that I'm in to work on that, full
bore

In that case, options two and three are eliminated. When the CEO says they want all hands on deck, going in and saying you want to take your vacation right now and hopefully could have some more is out of the question.

Stay, do your job and send your family. No extra money spent. No bummed family. No CEO lecturing you on what full bore means. No manager upset you're making them look bad. No co-workers upset that you're not a team player. Best case scenario - CEO knows what he's talking about things go big, and you profit considerably. You use that profit for a much nicer vacation in the future. :-)

This is the chance you take

You had the employer travel opportunity, and without their consent or agreement to absorb your risks, you tacked on a family vacation which was too dependent on their plan.

Obviously the company doesn't mind if your family stays in the company-provided room for free; it costs them nothing extra, so they don't try to charge your family for their fraction of the room. That does not make it a percolative, it's merely a happy accident, a use of spare resources.

Imagine if the company planned a private jet to Los Angeles with extra seats, and they let your family pile on, because it cost nothing extra. If the company cancelled the flight at the last minute... The right answer is "Well, thanks for the offer anyway" not "you cheated me, you need to pay for my family's commercial airfare". Can you see where that would be so?

The risk had always been there that the employer could change their plans due to the exigencies of business. And if they do, they don't owe you anything. You tried to get something for nothing... And it didn't work out. You weren't being exploitive, you weren't stealing, but you weren't entitled to it either and you are carrying on as if you were entitled.

The company didn't fool you, you just didn't think through the various risks. You are not losing money, because that would imply you were entitled to something, you just aren't getting to leverage the company's investment in the way you hoped.

In the future, yes, you need to plan your contingencies accordingly. My family never expected business trips to line up with vacay's, and made vacation plans that could line up, but also standalone if business plans changed.

In the future, I suggest buying insurance with your plane ticket. You'll be fully reimbursed if you decide to cancel. Right now, all you can do is hope you can get credit for a future plane ticket depending on where you bought the ticket. You'll still lose hundreds of dollars though.

In my opinion you should always buy insurance along with your ticket booked months (or weeks) in advance, even during normal times. You just don't know what sort of problems can arise.

I always do and it saved me a couple of times. Like many folks, I learned the hard way. I bought a airplane ticket and had to cancel at the last second. I got credit that I had to use in a year or lost it. I lost about 300 bucks since the ticket I used the credit for was way cheaper than the original tickets.

IANAL, but I would think a judge would determine that you could have bought insurance, but didn't do so and understood things could be cancelled. Unless you signed an agreement that you are 100% going to go then I don't see how you'd win.