Flights from Chicago to Kauai, Oahu and Maui are available starting at just $388 roundtrip, with several dates and trip lengths available!
I’ve listed several options below, but don’t be afraid to play around with the dates. There are more available than what’s listed, including different lengths of stay, so you may be able to build anything from a shorter getaway to a longer island vacation.
We’re seeing discounted Hawaii fares across several Midwest markets right now, and the prices are simply too good not to share. From Chicago, getting to Hawaii for under $400 roundtrip is an especially strong value.
Explore the Nā Pali Coast and Waimea Canyon on Kauai, visit Waikiki, Pearl Harbor and the North Shore on Oahu, or head to Maui for the Road to Hana, Haleakalā, beaches and winter whale watching. With three islands to choose from and fares starting at $388 roundtrip, there are plenty of ways to turn this deal into a winter escape.
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The Flights
Kauai
Oahu
Maui
