Disneyland Aulani Combo Vacation

This sounds so fun! I live in Cali -- please check the news regularly as currently, CA has a 10-day quarantine requirement for anyone traveling from out of state. I would HOPE that would be lifted by June, but if it is still in place, you will need to alter your plans. The quarantine does not apply if you are simply connecting a flight.
Thank you. I think they are doing exception if you have a negative covid test, which we will be doing to come there but if they need it for us when we return from Hawaii we will need to find a place to do another test. Finding testing locations and making sure results come in time is starting to be the stress factor of booking this great vacation.
 
May and September are both nice weather for DL and Hawaii, so no worries there. September may be slightly less crowded.

Try to stay at the Disneyland Hotel or Grand Californian if you can afford it. If not, I would personally skip Paradise Pier and stay at an off-site hotel that's within walking distance. 2 days at DL should be plenty to hit what your family wants to go on, but if you get an early enough flight you could also hit some rides your arrival night.

Aulani is amazing but I highly suggest you have a car and explore Oahu. Food choices at the resort are pretty limited, and there is a lot more available right down the highway.

Pearl Harbor and the North Shore are must do's. There are also several hikes and lookouts around the island. I really enjoyed the hike to Ka'ena Point, Kawela Bay Beach Park, Makapuu Point, and the Halona Blowhole.

There are some great coral reefs to snorkel at, and you can take beginner surf lessons around the island.

Suggested schedule:

Day 1 - fly to LA, get to DL, enjoy Downtown Disney
Day 2 and 3 - Disneyland w/ park hoppers and Max Pass
Day 4 - Fly to HNL
Days 5 - 9 - Full days in Hawaii. At least 2 days outside the resort, more if you rent a car for the whole stay
Day 10 - Day at Aulani, red-eye back to Chicago

You might be able to add one day to DL and subtract one from Hawaii, but I would really recommend as much time on the island as possible. It's a lot easier to get back to Disneyland.
 
The only flights going back to Chicago will be a red eye. I’ve done it many times, and lived on Oahu. We typically get at most a half day on departure; I’ve done anything from 3:30 take off (my next trip will be that as it’s a nonstop to Dulles) to an 8:30pm departure where I’m seriously kind of wiped out at that point. My DH will shower in the resort’s showers by the pool (Marriott’s Ko Olina), but I’m showered at check out which is 10:00 am. So I’m hot and sweaty a bit, now opting for earlier departure and we’ll use the United lounge at HNL for some lunch (flying first class and have a lounge pass).

I do recommend if you can to book first coming home; AA has lie flat seats to Chicago (or they did the last time I flew through there; it’s been a few years since then).

I like the late departures since I can actually sleep on the plane.
 
I like the late departures since I can actually sleep on the plane.
Going from HNL to the east coast (in our case MCO) we also like the red-eye flights. Our usual flight on Delta leaves HNL about 4 pm and arrives in ATL about 6 am. So, we get on board, have a pre-departure beverage. Once airborne and meal service happens we enjoy what they are serving, perhaps while watching a movie and then its time to go to sleep for the rest of the ~10 hour flight.
 


Going from HNL to the east coast (in our case MCO) we also like the red-eye flights. Our usual flight on Delta leaves HNL about 4 pm and arrives in ATL about 6 am. So, we get on board, have a pre-departure beverage. Once airborne and meal service happens we enjoy what they are serving, perhaps while watching a movie and then its time to go to sleep for the rest of the ~10 hour flight.

I prefer longer flights as well. When Delta has the nonstop HNL to Detroit it's perfect, leaves at dinner time and arrives at 7 am the next day.
 

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