Route Price Intelligence
Cheap Flights From Chicago to Maui
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Maui flights from ORD usually go for about $848, but Alaska Airlines has this route down to $475, a 44% discount. We're seeing availability from November through February, ideal for escaping Chicago winter for Kaanapali beaches. Alaska's strong track record on Hawaii routes makes this an easy one to book with confidence.
✓ 14 date combinations found at this price
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Best Time to Fly from Chicago to Maui
The cheapest time to fly from Chicago to Maui is typically May, when fares average around $612. The most expensive month tends to be December at around $848. For the best deals, consider flying in May, April, January.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route