• Which airlines operate flights from Chicago to Hawaii? United Airlines is the only carrier that flies direct between Chicago and the state of Hawaii. United flies to the island of Oahu and the island of Maui.

  • United Airlines is adding new flights to Hawaii from four cities, including Chicago. United will have nonstop flights between Chicago and Maui five days a week starting Dec. Chicago-based United currently only flies that route on Saturday, in addition to daily nonstop flights to Honolulu.

    One may also ask, what airlines fly direct from Chicago to Honolulu? United Airlines (2 times daily), Air New Zealand (2 times daily), American Airlines (2 times daily) are the most frequent flyers on this route.

    Moreover, does Southwest fly from Chicago to Hawaii?

    Theres no easy way to get to Hawaii on Southwest from Chicago or most cities outside the West Coast given the airlines initial focus on nonstop flights from California. (And forget about booking a return ticket without an overnight stay in California.) The routing: Chicago-St. Louis-Oakland-Honolulu.

    What airlines fly to Hawaii?

    The 6 Best Airlines That Fly to Hawaii

    1. Hawaiian Airlines. Fittingly, Hawaiian Airlines offers some of the best flights to Hawaii, providing daily service to Hawaii from more North American cities than any other airline.
    2. Alaska Airlines.
    3. American Airlines.
    4. United Airlines.
    5. Allegiant.
    6. WestJet.
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