All the above is really good input. On the other side, I am exactly the kind of person to try to fit in Disneyland with an Aulani trip, as long as I was headed that direction anyway
I have never had the luxury of taking a 14-day vacation so I am always trying to fit in as much as possible.
Obviously, if you COULD extend this trip even by a night or two, it would help. Another day on Oahu and 3 full days at DL (so 4 nights ) would be about my ideal. 2 days at DL isn't quite enough but it can be, if that's all you have. With 3 days you can really soak up the DL vibe.
Limiting myself to 10 nights, I would do 7 nights in Hawaii and 3 nights at Disneyland. You could put DL on either side, coming or going. I like what the PP said about putting DL on the way home to break up the trip, and to have something to look forward to.
Air travel: Trying to do both, I would prioritize efficient travel above all else. No connections. Purchase air travel as a series of one-way tickets. Take the (one) nonstop from ORD to HNL. From HNL, take the ONE nonstop into Long Beach (LGB) on Hawaiian -- do that to avoid LAX if at all possible (in Long Beach you are an easy 30-minute ride share or drive from DL, plus LGB is a tiny, easy airport to deal with). To get home, do nonstop from SNA (Orange County) into Chicago on your departure day. Again, avoid LAX at all costs (which may be literal as SNA is a more expensive airport in general).
Day 1 - Travel day, nonstop to HNL (9 hour flight landing mid-afternoon)
Days 2-7 -- Visit Oahu. This gives you 6 full days (7 nights) there to relax and explore.
Day 8 - Travel day, HNL to LGB, arrive late (nonstop departs HNL 11:30am arrives 8pm, as you lose 2 hours)
Days 9-10 -- Visit DL (3 nights at DL)
Day 11 - Travel day home (you could fit in some bonus DL time in the morning if you take an afternoon flight out of SNA and are willing to arrive home late). If you stay in one of the DL Resorts, you could do the early entry to DCA and get quite a bit done in a couple of hours (assuming they have early entry by that time)
To maximize efficiency, I would try not to change hotels on Oahu -- just rent a car and plop yourself in a 1-BD villa at Aulani (rent DVC points for the best price and to save nightly parking fees). I say a 1-BD as most people seem to agree that having a kitchen is pretty important to have the flexibility of eating in. I recently booked a 1-BD using rental points and found the Island View the best bang for my buck. Check the DVC
point charts for the weekly rate and plan your trip dates accordingly, as the dates have a direct impact on the cost -- one week in a 1-BD Island View currently ranges from 245-350 points depending on the season, so if you are renting at $20/point, you are talking $4,900 vs. $7,000 for one week the same room over different dates.
For DL, if it's in your budget, stay at the DL hotel (usually around $500+/night) or the Grand Californian (usually around $650+/night) for the extra touch of magic and convenience. If that is more than you want to spend, stay at the Howard Johnsons down the street -- it is freshly renovated, convenient, and everything you need at a
much lower price point (typically around $200+/night depending on the season). There are other hotels close by DL on Harbor Blvd. and I would choose one of those, if not Hojo's (and FYI Mouse Savers has a discount code for Hojo's). I would not stay anywhere that was NOT under a half mile from the actual DL entrance on Harbor (easily walkable). Again, efficiency is key and for SURE You don't want to drive or even bother with a ride share if you can avoid it.
Good luck planning!