Not sure which is the best forum for this kind of question, but I need help figuring the best way to get this done.
We'll be flying to Perth from Chicago. After a week or so, we'll be heading to Maui for a couple weeks, and then home to Chicago.
Any help will be appreciated.

Welcome to the forum

I am not sure what your question is.
- Paying cash?
- Or hoping for an award?
- Want to get miles into an airline freq flyer program?
- Looking for the cheapest fare?

Via Asia to Perth may be the best way

Airline information
Airlines that fly in Australia domestically
- Virgin Australia (Delta partner)
- Jetstar (a low cost, low quality carrier owned by QF)
- Qantas [OneWorld]
- Tiger Airways (a low cost, low quality carrier with low fares part owned by Virgin Australia)
- Regional Express Airways (REX) Regional airline

Airlines that fly USA/Canada to Australia (most from LAX) are
- United [Star Alliance]
- Qantas [OneWorld Alliance] (AS partner)
- Delta [Skyteam Alliance] (VA & AS partner)
- Virgin Australia (DL partner)
- Hawaiian, via Hawaii (AA DL & VA partner)
- Air NZ, via AKL [Star Alliance]
- Fiji Airways, via Fiji (AA & AS partner)
- Air Tahiti Nui (last segments on codeshares) (AA & DL partner)
- Air Canada [Star Alliance]
And others via Asia & Middle East

Welcome to FT kgilby

While I find that Cathay is my preferred airline USA --> PER, adding Maui on the return makes that problematic. Leaving QF as the likely OneWorld option. Issues in finding DL ticketing options is an exercise for others. And OW circle Pacific tickets will be relatively expensive but might be worth checking.

Consider LAX-xxx-PER (where xxx = BNE/MEL/SYD) on the inbound and
PER-SYD-HNL-LAX on the return with a separate ticket to Maui. You can try the QF online multi stop option though I think a travel agent might do better.

If flying discount economy explore adding ORD-LAX to the ticket. In premium cabins likely to be less expensive with separate AA tickets ORD-LAX. And perhaps HNL-ORD.

Happy wandering and let us know the outcome.

Fred

The price to include Maui in this itinerary shoots the cost up dramatically. Booking just Chicago/Perth roundtrip would cost about $3,500 US. Adding Maui turns that into about a $9,000 trip - unless I'm missing something.
Talking with a United rep, the circle Pacific(?) tickets would only get us from San Francisco on - we'd have to book an add'l. flight from Chicago to San Fran. And then, when traveling from Perth to Maui, we'd have to travel back to either LAX or San Fran and THEN BACK to Maui.
I'm getting ready to let Maui go - seems adding $5,500 to our costs JUST TO GET THERE makes little sense. (Right now we could book Chicago/Maui for about $1,600 for both of us)
HELP?

Hawaiian shows HNL-Maui at most $160 rt.
Note QF flies SYD-HNL 3x weekly.

ord-hnl round trip on AA runs $700-900 for random selection
hnl-syd-per-syd-hnl sample on QF is $2250

Alternative ord-lax-mel-per-syd-hnl on QF is $2053
one way HNL-ORD $400-600 with "wierd" routing
more direct maybe 800-900

Use multi city with the QF USA web site.

Likely even less expensive if you try Jetstar on HNL-SYD. That's QF's contribution to low cost flying. No miles credit to AA.

Happy wandering

Fred

I got a price of $5,850 total, for 2 for this itinerary. Sound like it's in the ballpark?

Seems about right for what you asked for.

A bit more than a premium Y round trip (E class) ORD-HKG-PER on CX.

Happy wandering

Fred

Thanks Fred, but I couldn't recreate your itinerary. Cathay Pacific only lets me input 4 cities into a Multi-City trip.
When I created ORD HKG PER HONOLULU, it cost $8600+ USD, which didn't get me to Maui, or get me back to Chicago.
What am I doing wrong?
Thanks
Ken

The CX quote was based on a simple round trip ORD-PER (in PEY).

Airlines do not make it simple to determine the most efficient route either time wise or money wise.

Happy wandering

Fred