When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 28 days in advance, which can save you up to 11% on flights from Chicago Midway to Hawaii compared to booking the week you need them. Waiting 28 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $546. For sooner than that we have options available in the next 3 days from $555.
Flights from Chicago Midway to Hawaii lean towards being more expensive in June. Prices are generally better when you fly from Chicago Midway to Hawaii in September, with the cheapest ticket starting at $355.