Cheap flights to Hawaii from Chicago

Round trips from Chicago from $251. Cheapest dates, deal ratings and where to book.

• Lihue, Kauai: $251, 2027-01-23 to 2027-02-09
• Honolulu, Oahu: $602, 2026-11-01 to 2026-11-08
• Kahului: $710, 2027-01-18 to 2027-01-23

Nearby

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• Alaska
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