Multi-City Flight question
 

Good afternoon! Later this year, we will be visiting Osaka, Japan for a week. This travel itinerary is set. We'd like to add some other destinations on to this trip.

We'd like to fly from Chicago to Tokyo - stay for a few days - then take the bullet train to Osaka for our visit to Osaka/Kobe area. We would like to leave from Osaka and go to Hawaii for a few days/week, then fly back to Chicago.

I'm not sure how to book these flights. Would these all be one way tickets? Would I do some kind of multi-city combination? Any tips you can provide would be greatly appreciated. All the travel agents in my area mainly specialize in cruises so I haven't contacted one. If there's a way to find someone that would specialize in this kind of trip, I'd be glad to consult with them.

I appreciate anyone who can share some expertise. I try to be a savvy traveler but I'm having trouble with this one! Thank you!

Multi city is probably your best bet in terms of taking advantage of any open jaw/stopover faring. One ways could get you better timing on each flight.

Looking at multi-city options on Google Flights - the best flights are all different airlines and are booked separately. Will this cause me problems? Thank you.

Nothing major - when you don't book separately, the airline can't send your return flight information to the immigration systems, so you may have to prove you have reservations booked to leave the country. I've never had an issue pulling this up and showing on my phone, but if you don't know, or won't, have cell service, a paper copy may be handy. Sometimes they ask, sometimes they don't.

You also won't be protected in the case of a delayed flight (or bag). Not an issue (or very very unlikely to be) if you're staying multiple nights in each destination. The airline should deliver a bag to any address, but it gets complicated when you've continued on from that destination, especially on a different ticket on another airline.