Deal found on October 22, 2026
Chicago to Maui
$475$70433% off
Round trip
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.
Travel dates
Dates in February
e.g. Feb 1 – Feb 10 · 9 nights
Date options
14 at this price
Lowest we've seen
$330
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