Award prices change daily. Every number here is a starting price for saver space booked well ahead; search live before you transfer points.
Maui to Chicago is about 4,178 miles (OGG–ORD). You can fly it nonstop on United and American. The cheapest way to book it on points is usually Air Canada Aeroplan from 22,500 points one-way on United, with $5.60 + ~$30 fee in taxes. That's a lot of trip for the points: Chicago means Millennium Park and Art Institute of Chicago.
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Quick answer
- Cost: from 22,500 points one-way in economy; premium cabins from 35,000 with Air Canada Aeroplan.
- Book with: Air Canada Aeroplan on United nonstops; Turkish Miles&Smiles is the backup.
- Transfer from: Chase Ultimate Rewards, Amex Membership Rewards, Capital One miles and Bilt Points.
- Taxes: $5.60 + ~$30 fee one-way.
- Catch: Aeroplan only sees United saver space, and United can price above the chart.
Free tool: see what your Chase, Amex, Capital One, Citi or Bilt points become at every airline and hotel, with live transfer bonuses at kritdeals.com/transfer-calculator, or in the free KritDeals app for iPhone and Android.
At a glance
| Program | Flies on | Economy from | Premium from | Taxes |
|---|---|---|---|---|
 Delta SkyMiles |
Delta (1 stop) |
~15,000 | 40,000 (First) | $5.60 |
 AAdvantage |
American |
~20,000 | — | $5.60 |
 Air Canada Aeroplan |
 United |
22,500 | 35,000 (Business) | $5.60 + ~$30 fee |
| United MileagePlus |
United |
~22,500 | 45,000 (First) | $5.60 |
 Air France-KLM Flying Blue |
Delta (1 stop) |
~24,000 | — | about $20–30 |
 Turkish Miles&Smiles |
United |
25,000 | 40,000 (Business) | $5.60 |
One-way, per person, starting prices. A ~ marks a typical or rarely seen price, not a published chart price. Dynamic programs (AAdvantage, MileagePlus, SkyMiles, Flying Blue) can cost several times more on peak dates.
How each airline prices Maui to Chicago
Every program uses its own method, which is why the same seat can cost very different amounts. Here's the math for each program that books this trip, cheapest first:
- Delta SkyMiles (on Delta, 1 stop): Dynamic pricing. Delta sets the price of its own flights by demand, like a cash fare; there's no chart. About 15,000 is the lowest economy price seen to Hawaii on off-peak dates, and about 40,000 in first. Busy dates can cost several times more.
- AAdvantage (on American): Dynamic pricing. American sets the price of its own flights by demand, like a cash fare; there's no chart. About 20,000 is the lowest economy price seen to Hawaii on off-peak dates. Busy dates can cost several times more.
- Air Canada Aeroplan (on United): Distance chart. Aeroplan prices United flights within North America by total distance. The 4,178-mile nonstop falls in the 2,751+-mile band: from 22,500 economy, 35,000 business, plus a booking fee of about $30. That's the starting price; United can release seats above it.
- United MileagePlus (on United): Dynamic pricing. United sets the price of its own flights by demand, like a cash fare; there's no chart. About 22,500 is the lowest economy price seen to Hawaii on off-peak dates, and about 45,000 in first. Busy dates can cost several times more.
- Air France-KLM Flying Blue (on Delta, 1 stop): Dynamic pricing. Flying Blue prices Delta flights by demand, with no chart, and since September 2026 the price also depends on the fare type you pick. Trips this long have been seen as low as 24,000 in economy, often below SkyMiles for the same seat. Taxes are higher, about $20–30.
- Turkish Miles&Smiles (on United): Zone chart. Turkish charges one flat price for United flights to or from Hawaii, whatever the distance: 25,000 economy, 40,000 business.
- Avianca LifeMiles (on United): Unpublished chart. LifeMiles doesn't publish its prices for United flights and changed them without notice in 2025. About 25,000 is what it has been charging for a trip like this; check lifemiles.com before you transfer.
- Cathay Asia Miles (on American): Distance chart, whole trip. Cathay Asia Miles prices American and Alaska flights by total distance. The 4,178-mile nonstop falls in the 2,751–5,000-mile band: 27,000 economy, 63,000 business.
Nonstop flights from Maui to Chicago
| Airline | Airports | Service |
|---|---|---|
| United |
OGG–ORD | Year-round |
| American |
OGG–ORD | Seasonal winter; begins Dec 17, 2026 |
What it's worth
A useful test: bank points are worth about 1.5 cents each when you could use them elsewhere. So 22,500 points is a good deal when the cash fare is above about $374. On Maui–Chicago, that's common on busy dates and in the last few weeks before travel, when fares jump and fixed award charts don't. For a premium seat, 35,000 points pays off when the cash fare tops about $561. See our points valuations for each program.
How to book
Air Canada Aeroplan
Aeroplan books United saver space by distance: 22,500 in economy, 35,000 in business on United's OGG–ORD nonstop. Add a stopover for 5,000 points. Feeds: Chase Ultimate Rewards 1:1, Amex Membership Rewards 1:1, Capital One miles 1:1, Bilt Points 1:1 and the Chase Air Canada Aeroplan Card.
Delta SkyMiles
Delta SkyMiles prices its own flights dynamically. Off-peak economy starts around 15,000 and first around 40,000 on Delta with one connection. Delta prices track cash fares. Search the flexible-date calendar and wait for SkyMiles flash sales (domestic 5,000-10,000 one-way). Feeds: Amex Membership Rewards 1:1 and the Delta SkyMiles Gold American Express and Delta SkyMiles Platinum American Express.
AAdvantage
AAdvantage prices its own flights dynamically. Off-peak economy starts around 20,000 on American's OGG–ORD nonstop. Search the calendar view and target off-peak months (mid-Jan to mid-Mar, Sep to mid-Nov). AA runs periodic 7,500-mile domestic sales. Feeds: Citi ThankYou 1:1 and the Citi / AAdvantage Platinum Select card.
United MileagePlus
United MileagePlus prices its own flights dynamically. Off-peak economy starts around 22,500 and first around 45,000 on United's OGG–ORD nonstop. Holding a United co-brand card (from 2026-04-02) takes at least 10% off every United-operated award (15% if also Premier) and unlocks more saver space. The discount is displayed to everyone, but only cardholders get it. Feeds: Chase Ultimate Rewards 1:1, Bilt Points 1:1 and the United Club Business Card.
Finding availability
- Book early. Schedules open about 330–337 days ahead on the US airlines. Saver seats are easiest to find in the first few weeks and again in the last two weeks if planes aren't full.
- Search the airline's own site first. Delta.com, aa.com and united.com show the seat; then price the same flight with each partner program.
- Use flexible-date calendars. One day either side often halves a dynamic price.
- Transfer last. Bank transfers are one-way. Find the seat, then move exactly the points you need.
- When to go: May–October is best, with June–September bringing festivals and outdoor dining; winters are very cold, though hotel rates are lowest then.
Who should do it
- Anyone holding Amex Membership Rewards, Citi ThankYou, Chase Ultimate Rewards and Capital One miles: they move into these programs.
- Travelers with fixed dates on busy weeks, when cash fares spike but chart prices hold.
What to do in Chicago
- Millennium Park: A lakefront park with Anish Kapoor's Cloud Gate ('The Bean'), Crown Fountain and free summer concerts at Pritzker Pavilion.
- Art Institute of Chicago: An encyclopedic art museum next to Millennium Park known for its Impressionist collection and American Gothic.
- Chicago Architecture Center River Cruise: A 75-minute docent-led boat tour of downtown's architecture along the Chicago River, running roughly April–November.
- Museum Campus: The Field Museum, Shedd Aquarium and Adler Planetarium on the lakefront south of downtown.
- Willis Tower Skydeck: An observation deck on the 103rd floor with glass-floored ledge boxes.
Getting around: You don't need a car: the CTA 'L' Blue Line runs from O'Hare and the Orange Line from Midway to the Loop, and downtown is walkable.
Hotels you can book on points: Park Hyatt Chicago (Hyatt), InterContinental Chicago Magnificent Mile (IHG) and The Ritz-Carlton, Chicago (Marriott).
Which card to earn with
| Card | Points | Transfers to | Best for |
|---|---|---|---|
| Chase Air Canada Aeroplan Card | Air Canada Aeroplan |
— (earns it directly) | Earning Air Canada Aeroplan directly |
| American Express Gold Card | Amex Membership Rewards | Delta SkyMiles and Air Canada Aeroplan | The Air Canada Aeroplan booking |
| Chase Sapphire Preferred | Chase Ultimate Rewards | Air Canada Aeroplan and United MileagePlus | The Air Canada Aeroplan booking |
| Bilt Obsidian Card | Bilt Points | Air Canada Aeroplan and United MileagePlus | The Air Canada Aeroplan booking |
| Citi Strata Premier | Citi ThankYou | AAdvantage |
AAdvantage bookings |
Annual fees and welcome offers change; each card page has today's terms.
FAQ
How many points does it take to fly Maui to Chicago? From 22,500 points one-way in economy with Air Canada Aeroplan, or 25,000 with Turkish Miles&Smiles. Delta SkyMiles can dip to about 15,000 on its cheapest dates, but don't count on it. Peak dates on dynamic programs cost much more.
Is there a nonstop from Maui to Chicago? Yes, on United and American. See the table above for airports and seasons.
Which credit card is best for Maui to Chicago? For this route, the Chase Air Canada Aeroplan Card is the most direct fit, since it earns Air Canada Aeroplan directly. If you'd rather keep your options open, the American Express Gold Card earns Amex Membership Rewards that move to Delta SkyMiles and Air Canada Aeroplan.
How far ahead should I book? As early as the schedule opens (about 11 months), or watch for saver seats in the final two weeks. Transfer points only once you've found the seat.
Related guides
- Chicago to Maui with points
- Delta Amex cards guide
- Citi AAdvantage cards guide
- Aeroplan guide
- OGG airport lounges
- ORD airport lounges
- Transfer partners: Chase, Amex, Capital One, Citi
- What points are worth
Award prices and availability change daily. Search before you transfer points — transfers are one-way.
