Compare 6 loyalty programs for Chicago to Maui (Kahului) award flights, with economy seats from 22,500 points.
Chicago to Maui (Kahului) is a long-haul domestic route to Hawaii, and nonstop award space shows up on United Airlines. It's priced by six programs, and the cheapest economy award is 22,500 points via American AAdvantage. Program choice is the lever: the same seat often prices differently across programs, so compare before you transfer. This page compares every way to book ORD–OGG on points.
Best one-way award prices per airline over the next 12 months.
| Airline | Economy | Premium economy | Business | First |
|---|---|---|---|---|
 American AirlinesAA | 22,500Lowest | 32,500Lowest | 90,000pts | 50,000Lowest |
 Alaska AirlinesAS | 22,500Lowest | Not available | Not available | 50,000Lowest |
 DeltaDL | 23,700pts | 102,400pts | Not available | 96,300pts |
 United AirlinesUA | 25,000pts | 98,400pts | 86,900Lowest | 90,000pts |
When award seats between Chicago and Maui (Kahului) price cheapest over the next year.
| Month | Cheapest award (points) |
|---|---|
| Nov 2026 | 22,500 |
| Dec 2026 | 22,500 |
| Jan 2027 | 22,500 |
| Feb 2027 | 22,500 |
| Mar 2027 | 35,000 |
| Apr 2027 | 22,500 |
| May 2027 | No award data |
| Jun 2027 | 25,000 |
| Jul 2027 | 56,100 |
| Aug 2027 | No award data |
| Sep 2027 | No award data |
| Oct 2027 | No award data |
4 airlines with award seats between Chicago and Maui (Kahului), nonstop or connecting.
American AirlinesAAAlaska AirlinesASDeltaDLUnited AirlinesUAWhat to know before booking Chicago to Maui (Kahului) with points.
~4,180 miles; ~8h55 nonstop (approximate). Maui (Kahului) runs 5 hours behind Chicago (4 while Chicago is on standard time). Data covers November 2026–October 2027, with calendar prices for eight months. Counting well-covered months only, November 2026–January 2027 are among the cheapest, at 22,500 points, while March 2027 (35,000) and June 2027 (25,000) run higher.
Chicago to Maui (Kahului) is served by American Airlines, Alaska Airlines, Delta and 1 more, offering multiple options for award travelers. Compare 6 loyalty programs to find the best value for your points. Award prices start from 22,500 points in economy. Use our search tool to check real-time award availability on this route.
Flying Chicago to Maui (Kahului) covers about 4,180 miles, linking O'Hare International Airport (ORD) with Kahului Airport (OGG); a nonstop takes roughly 8h55, with winds moving it either way. Nonstop award space in the data comes from a single airline: United Airlines. The Boeing 787-8 appears on those nonstop award segments. Expect mostly connecting results: only about 3% of the award options in the data are nonstop.
Chicago–Maui (Kahului) is domestic but long-haul, so book it cabin first, then program. The economy floor connects once; an economy nonstop on United Airlines costs more. Taxes and fees on the cheapest economy seat run about $6, in line with the route's typical economy taxes. The middle step, premium economy, costs about 1.4 times economy; business costs about 3.9 times. First class undercuts business here, so price it before settling. Hold off on converting flexible points until the seat is confirmed bookable; there's no undoing a transfer.
American AAdvantage takes economy at 22,500 points. Alaska Atmos Rewards is cheapest in premium economy at 32,500 points and first class at 50,000. United MileagePlus wins business class at 86,900 points. Delta SkyMiles, Avianca LifeMiles, and Etihad Guest also price the route and are worth a cross-check before transferring. No program wins more than two cabins here, so pick the seat first, then the currency.
In the current award data, only United Airlines shows nonstop space on Chicago–Maui (Kahului), but as a Star Alliance member its seats also price through alliance partners, not just United MileagePlus. Partner pricing sets the premium-economy floor: Alaska Atmos Rewards books American Airlines as a oneworld partner, and no program prices American Airlines lower in that cabin at last check. Only four airlines hold award inventory on the route, yet six programs price them, so the competition is between currencies more than carriers.
The data shows no same-metro alternate airports on either end of Chicago–Maui (Kahului), so date flexibility is the main lever. Out of Chicago, Athens (9,500 points) and Anchorage (10,000) are cheaper redemptions at last check. For a shorter trip from Chicago, Aruba and Auckland are tracked too.
Alternative corridors travelers consider alongside Chicago to Maui (Kahului).
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Common questions travelers ask about the Chicago to Maui (Kahului) route.
