Route notes
Why this routing works
This itinerary is a straightforward two-stop Hawaii routing built as a single multi-stop ticket: Chicago to Honolulu, onward to Lihue, then return to Chicago. With 3 nights in Honolulu followed by 7 nights in Lihue, the sequence keeps the inter-island segment in the middle instead of splitting the long mainland flights across separate bookings.
At two weeks total in economy, the pacing leaves room for both Hawaii stops without adding extra flight legs. Starting in Honolulu and continuing to Lihue also avoids backtracking between islands, which helps keep the route clean and the timing simple.
From a ticketing standpoint, this is priced as a multi-stop itinerary rather than separate one-way flights. Based on the sold route data, the economy fare range runs from $846 to $1,108, with January departures in the Jan-Mar season.