Hawaii - AirFare Question and other stuff

I am not sure if I can do this, but the best price for airfare is to book multiple legs; Newark to Chicago, Chicago to Honolulu, then five days later HNL to OGG and on the way back HNL to LAX, LAX to EWR.

Will the airlines know to transfer my baggage? This is the first time on such a long flight so I'm not sure if I could break it up like this.


Also can 4 people stay in 1 hotel room, family of 4?

I have heard that I don't need a car in Wakiki but should we rent a car in Maui.

Any restaurant or must see recommendations.

If you book a flight that connects through a city, then the airline transfers your checked baggage.

While you don't need a car much in Waikiki, it is best to have one to explore areas such as the North Shore, Pearl Harbour, etc... so I'd definitely have one. You absolutely need on on Maui - it's the second largest island in the Hawaiian Island chain.

While a family of four typically can fit into one hotel room, it generally requires 2 per bed. For my comfort, that is too much togetherness! We always have two rooms (our children are both over 10). Remember, you will have some who, due to the 6 hour time change, will wake up at 3am, and you don't want to wake others up!

I recommend buying some good guidebooks!

I am not sure if I can do this, but the best price for airfare is to book multiple legs; Newark to Chicago, Chicago to Honolulu, then five days later HNL to OGG and on the way back HNL to LAX, LAX to EWR.

Will the airlines know to transfer my baggage? This is the first time on such a long flight so I'm not sure if I could break it up like this.


Also can 4 people stay in 1 hotel room, family of 4?

I have heard that I don't need a car in Wakiki but should we rent a car in Maui.

Any restaurant or must see recommendations.
It sounds like you're booking airfare separately, e.g., EWR-ORD/MDW on one ticket, ORD/MDW-HNL on a separate ticket (but same airline?). If you're doing this, be advised that the second airline has no obligation to get you to HNL if your EWR-ORD/MDW flight is delayed and you miss your onward flight. This applies even if you're flying the same carrier on both tickets. Same for the return.

Bottom line: If you're going to be booking separate tickets, make sure to allow for an adequate connection, and hope that there's no weather/mechanical that delays your first flight.

As for Waikiki, you might consider doing a one day car rental when needed. Lots of information on this forum about that, and searches will bring up relevant info.

I think buying so many separate tickets may be an issue if one flight is cancelled or delayed. Unless you give yourself ample time in each connection. Most airlines will connect the luggage (interline) even if you are flying different airlines but that may be an issue if each airlines charges separate for the bag; if the bags arrive late or do not arrive you will be caught in the blaming game between them.
Why not just do EWR-HNL non stop with CO and then buy separate inter-island tickets? the benefits may outweigh the increase cost.
2 adults and 2 kids is totally doable in one room with 2 double/queen beds; in fact many hotels will give the kids a free breakfast if your room includes breakfast for two adults. It depends on your family, the age of the kids and what you want out of your vacation.
Car is Honolulu is +/-; I highly recommend at least one day of car to drive around Oahu island; while in Honolulu/Waikiki, you don't need a car.
In Maui I would get a car unless you are the type to just stay in the hotel, use the hotel facilities and restaurants and you just want to veg out on the beach/pool.

I imagine your flight to Honolulu baggage will be checked through.. then you would pick up baggage in Honolulu before checking your bags back in for OGG, and picking up at OGG. Once you board back from OGG to LAX and then back home, you bags would be checked through to home.

IMHO book rental cars on both islands, because you're there for a short visit, and will maximize flexibility while on vacation. Standard hotel rooms should fit 4.. I would do hotel room/condo research on www.tripadvisor.com

The flights are Newark to Chicago arriving at 9 am then the next flight from Chicago to HNL is at 11 am, would that be enough time. It will all be on AA, will they charge me baggage charges for both flights?

Also I want to arrive at HNL and depart from OGG (to EWR)

Thanks

When you check in, tell the agent you want them to interline your bags to HNL.

On the way home, you can do the same thing, even if you're flying Hawaiian Airlines and connecting to another airline.

In both cases, be prepared with your itinerary and boarding passes for all flights except the HNL-OGG segment.

The flights are Newark to Chicago arriving at 9 am then the next flight from Chicago to HNL is at 11 am, would that be enough time. It will all be on AA, will they charge me baggage charges for both flights?

Also I want to arrive at HNL and depart from OGG (to EWR)

Thanks
I personally would not risk it with a 2 hour layover on two separate tickets in a big hub city prone to delays, but what is your risk tolerance?

Another thought...

We actually just bring carry-ons usually, even for over a week to Hawaii. You don't need much at all, and can buy cheap snorkels at Costco or just rent them. We do laundry, and you don't need anything dressy. Wear walking shoes and pack sandals, swimwear, shorts, tees, a sweater and maybe wear long pants.

That could aleviate the risk of losing luggage.

Oh, and I just buy things like shampoo when we get there.