Milwaukee to Hawaii Starting at $404 Roundtrip

Great Lakes Travel Deals — Wed, 12 Aug 2026 13:44:31 GMT

Hawaii flight prices have dropped! Roundtrip flights from Milwaukee to Kauai, Honolulu, and Maui are available starting at just $404 for select travel dates from October through February.

Flights from Milwaukee to Hawaii are typically $550+ roundtrip, making this a great opportunity to escape the Midwest winter for significantly less than usual.

Each island offers a completely different experience. On Kauai, explore Waimea Canyon, the Nā Pali Coast, and some of the island’s incredible beaches and hiking trails. On Oahu, visit Waikiki Beach, Pearl Harbor, Diamond Head, and the famous North Shore. On Maui, drive the Road to Hana, visit Haleakalā National Park, relax on beautiful beaches, or go snorkeling and whale watching during the winter months.

I’ve shared several flight options below, but there are many more dates available at or near these prices. I’ve even found an option for travel over the Thanksgiving holiday.

Don’t want deals from every airport? Customize your flight alerts. Instructions found - HERE

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The Flights

Great Lakes Travel Deals: Wisconsin - Milwaukee (MKE)

Milwaukee to Hawaii Starting at $404 Roundtrip

Don’t want deals from every airport? Customize your flight alerts. Instructions found - HERE

The Flights

O’ahu

Maui

Kauai