Great Lakes Travel Deals: Wisconsin - Milwaukee (MKE)

Milwaukee to Hawaii Starting at $404 Roundtrip!

Great Lakes Travel Deals — Thu, 17 Sep 2026 00:28:44 GMT

Round-trip flights from Milwaukee to Hawaii are starting at just $404, with options to Kauai, Maui, Oahu and Hawaii Island and tons of winter travel dates are available.

There are also way more travel dates available than what we’ve published below. If the dates we listed don’t work for you, take a look for yourself and play around with the dates—there are several other options available at similar prices.

✈️ PAID SUBSCRIBER EARLY ACCESS: This flight deal was sent to paid subscribers 2 hours before its broader release.

Whether you want the beaches and Nā Pali Coast of Kauai, the Road to Hana and Haleakalā on Maui, Waikiki and the North Shore on Oahu, or volcanoes and the Kona Coast on Hawaii Island, there are plenty of ways to turn these fares into a great winter escape.

Anytime we see Hawaii fares drop into this range, especially with this many winter dates available, they’re worth sharing!

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The Flights

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

And if the deals have helped you save money or inspired a trip, please consider supporting my work with a paid subscription for just $30/year. ✈️

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The Flights

O’ahu

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Maui

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Kauai

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