I've never been to Chicago, but I will imagine I have! Thanks for the tip.
When I went a million years ago (I was only 15), we spent a few days on Waikiki and a few days in Kauai. All I really remember is that Kauai seemed much more remote, and very peaceful.
Wish my Grandma was still around so I could ask her what SHE enjoyed.
Kauai is still more remote and peaceful than the other islands, although the Big Island (Hawaii) is a close second. We went to both in Feb. of this year, primarily because my Hyatt Globalist benefits expired at the end of Feb. and we stayed at the Grand Hyatt Kauai...but also because we wanted to see whales and we had only visited HI in May previously.
That was our 5th trip to Hawaii in the last 15 years and we've visited Kauai each time (our favorite). It was our second trip to the Big Island. We've been to Maui twice and Oahu once (for one day). We don't have much desire to go back to Oahu, especially Wakiki since, as others have said, it's a big city. Parts of Maui also have that city feel, but it's still beautiful, has amazing resorts, beaches, snorkeling, etc. Kauai is our favorite because it is the most tropical, remote, laid back, etc.
A couple more points:
- With your UR points, the Grand Hyatt Kauai is a great option - some consider it the best Hyatt resort in all of Hawaii. The Andaz Maui is right up there with it as far as Hawaii Hyatt's go.
- I mentioned whale watching. If you're going in Jan. and the thought of seeing whales interests you, you might want to consider staying on Maui or the Big Island, at least for 2-3 nights. There are several hotels/resorts on the west sides of both islands that look directly into the major channels / waterways where the whales frequent. We didn't take a tour, but really enjoyed being able to see them from the shores and the resort (Hilton Waikoloa).