2 Round Trip Itineraries are Cheaper than 1?

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Moderators - please move this if it belongs somewhere else. This is just the only social media I use so I'm not sure how to ask the question.

We are beginning to think about visiting Tokyo Disney in 2024, and we noticed that tickets are SIGNIFICANTLY cheaper (as in thousands of dollars per ticket x 5 tickets) on United if we fly Newark - California and then California - Tokyo instead of booking from Newark all the way to Tokyo. But with airlines cracking down on skiplagging and other rule infractions I'm afraid to do something which may inadvertently violate their policies. I know that "nested tickets" may be if they are used to circumvent minimum stay requirements, but that wouldn't be the case here. Also we'd be flying 2 separate routes, instead of retracing our steps. Does anyone know for sure whether this is/is not ok? Otherwise I may break down and speak to a travel agent instead of booking myself, which is something I typically hate doing.

Thank you!
 
Moderators - please move this if it belongs somewhere else. This is just the only social media I use so I'm not sure how to ask the question.

We are beginning to think about visiting Tokyo Disney in 2024, and we noticed that tickets are SIGNIFICANTLY cheaper (as in thousands of dollars per ticket x 5 tickets) on United if we fly Newark - California and then California - Tokyo instead of booking from Newark all the way to Tokyo. But with airlines cracking down on skiplagging and other rule infractions I'm afraid to do something which may inadvertently violate their policies. I know that "nested tickets" may be if they are used to circumvent minimum stay requirements, but that wouldn't be the case here. Also we'd be flying 2 separate routes, instead of retracing our steps. Does anyone know for sure whether this is/is not ok? Otherwise I may break down and speak to a travel agent instead of booking myself, which is something I typically hate doing.

Thank you!
Can you stay overnight in LA? Used to be called open jaw.
 
You won't be allowed to check your luggage through. You'll have to claim your luggage then check it to Japan. International flights have earlier luggage check in deadlines and be at gate rules then domestic flights. Youll have no protection if you miss your CA to Japan flight. In other words if your first flight is delayed you may have to buy a new ticket from CA to Japan.

I'd only consider it if you have an overnight stay.

How long a connection in.CA?

A travel agent won't be able to help.
 

Self connecting is perfectly acceptable. As @Lewisc points out, you will not have any protections if you have any delays. Many people in the points and miles space do this and call it "positioning." They look for a cheap flight and then have to get themselves to wherever they found cheap tickets from. I would highly recommend not doing this with less than a 24 hour layover. Since you're talking United I'm going to assume EWR-LAX and then LAX-TYO? The reason is that EWR is a fortress hub for United and LAX isn't a fortress for anyone so they must compete on price at LAX.
 
Yes, that would be the plan. We may even do 1-2 nights in Disneyland on the way but that remains to be seen. Coming back I’m not sure how we do it but probably something similar. Honestly at some point it will come down to number of days we can be away (everyone’s schedule is insane and we need to work around school/sports/work)/ and having enough time in Japan vs saving enough to make the trip reasonable.
 
I’d also consider driving to JFK but prices aren’t that much better there, and all else close it’s helpful to have some measure of status on United.
 
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I think you will be fine with what you are planning as long as you have built in enough time for any delays with the first plane. I would make sure that the second plane trip was easy to reschedule or refundable if the first flight is cancelled/delayed.

I am currently planning a trip to Europe next year, though I keep looking at Asia and South America so that might change. I plan to look at all options for the best prices and figured I may need to do something similar to what you are planning.
 
What dates? I see non stop flights EWR and JFK to Tokyo for well under 1K one way. Some are on United metal but booked through ANA (airline)Use a site like kayak.
 
My mom wants to fly business class (if possible) and we need to do it over summer vacation (my husband is a professor). So we would either go right after school gets out and come back the weekend after July 4th or we would go the last 2 weeks of August, into Labor Day. We don’t have a ton of flexibility because my son has to be back so that he can be driven to sports camp the Sunday after July 4th and my daughter has her own sports camp starting that same week. My son also has Scout camp the first 2 weeks of August that he would be devastated to miss.

It’s still a little too early to be pricing out summer 2024 but late August 2023 pricing through LAX seems reasonable enough to swing business instead of premium plus.

Business seats are definitely a luxury but my husband has a hard time flying anyway (especially at night), so the idea of 16+ hours in coach would be really challenging. I want to do everything I can to make him - and the rest of us - comfortable. He has wanted to take me/the family to Japan for as long as I have known him (going on 30 years now).
 
Be careful. A couple of sites have great prices for business class tickets from NYC to Tokyo. Atound 2K one way..Fine print. Hidden City. Flight is to Vietnam with a connection in Tokyo. Many issues. Looking for trouble.

Another option offered is NY to Montreal connecting with Montreal to Japan. Layovers is 1 hour 13 minutes
 
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1:13 layover and also having to go through customs in Canada seems risky to me.

Good point about hidden cities. I was looking at specific nonstops but I’ll keep that in mind once it’s finally time to book. I mostly wanted to make sure this was actually a possibility.
 
I would not even think about hidden city ticketing on this kind of trip. Too many issues and if you get caught by United, you can pretty much kiss your status and all your points goodbye.
 
To be clear I’m considering booking a round trip nonstop flight from EWR to LAX on the 1st and the 15th and a nonstop round trip from LAX to Tokyo on the 2nd and the 14th (or something like that). No shenanigans except that the second round trip is in the middle of the first. So as someone said, it’s kind of a repositioning trip. I understand that we won’t be able to book through which is fine because we will likely spend the night in LAX on at least one of the legs and coming home we need to get bags from customs. The problem would be if our flight is canceled but I’ll check prices and decide if it is worth the risk.
 
I would not even think about hidden city ticketing on this kind of trip. Too many issues and if you get caught by United, you can pretty much kiss your status and all your points goodbye.
To be clear I was NOT suggested booking a
hidden city itinerary. OP mentioned using a TA. Hidden City is one technique used being used by bottom feeders.

Loss of points and status aren't the biggest issues. After booking you'll realize you have to satisfy entry requirements for your no show destination. That may include VISA, information regarding your accommodations and return ticket.
 

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