Route Price Intelligence
Cheap Flights From Chicago to Maui
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 6d ago
$434Chicago to Maui normally runs about $848, and Alaska Airlines just cut it to $434, essentially half price for one of the most requested beach destinations we track. We've only confirmed one date so far, but at this discount on Hawaii, it's the standout fare of the day.
✓ 3 date combinations found at this price
Search Google FlightsTypical Price
$704
Great Deal
Under $396
Typical Range
$396 – $734
Lowest We've Seen
$330
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$696
Feb
—
Mar
—
Apr
$674
May
$612
Jun
$731
Jul
$724
Aug
$704
Sep
$697
Oct
$704
Nov
$704
Dec
$848
Cheapest Average Expensive
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
Cheapest month: September34,971 fares analyzedTypical low: $644