Hawaii Flight Deals from Grand Rapids & Chicago – Starting at $337 Roundtrip!
We’ve got a rare wave of Hawaii deals right now—but I’ll be honest, it’s a bit messy to piece together. Different islands, departure cities, and travel windows—but if you’re flexible, the savings are huge. Here’s a breakdown to help you sort through the best options from Grand Rapids and Chicago. I’ve listed one flight for each route. If you’re interested in more options open one of the flights and navigate around to find other dates.
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🌺 From Grand Rapids (GRR):
GRR to Kauai – $423 Roundtrip
Travel in August and September
Typical pricing: $650+
🌺 From Grand Rapids (GRR):
GRR to Maui – $423 Roundtrip
Travel from August through November
Typical pricing: $650+
🌴 From Chicago (ORD):
ORD to Kauai – $337 Roundtrip
Travel from August through November
Additional dates available January through April for $423
Typical pricing: $550+
ORD to Maui – $387 Roundtrip
Travel from August through November
Typical pricing: $550+
Whether you're dreaming of the beaches of Maui or the lush cliffs of Kauai, these deals are some of the lowest we’ve seen all year—and they span peak fall, shoulder season, and even winter escape dates.
