Cheap Flights from Chicago to Maui
Cheap Flights from Chicago to Maui
Looking for cheap flights from Chicago to Maui? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Maui vary by season, cabin, and date, but available award flights can start around 17,500–22,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Maui for specific travel dates.
2026-12-18
ORD - OGG
Economy | Non stop | 1 left
From 17,500 Pts + $25.6
2026-12-27
ORD - OGG
Economy | 1 Stop | 5 left
From 17,500 Pts + $25.6
2026-12-31
ORD - OGG
Economy | 1 Stop | 4 left
From 17,500 Pts + $25.6
2026-11-09
ORD - OGG
Economy | 1 Stop | 9+ left
From 22,500 Pts + $5.6
2026-11-11
ORD - OGG
Economy | 1 Stop | 9+ left
From 22,500 Pts + $5.6
2026-11-16
ORD - OGG
Economy | 1 Stop | 9+ left
From 22,500 Pts + $5.6
Chicago to Maui flight facts
Distance
4,175 mi
6,719 km in a straight line
Estimated flight time
about 8h 45m
In the air, for the straight-line distance
Time difference
−4h
Maui is 4 hours behind Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Maui
OGG · Kahului
Nearby airport alternatives
Flights Milwaukee - Maui · Milwaukee is 73 mi from Chicago
Flights Chicago - Kona · Kona is 84 mi from Maui
Flights Chicago - Honolulu · Honolulu is 100 mi from Maui
Flights Grand Rapids - Maui · Grand Rapids is 142 mi from Chicago
Flights Indianapolis - Maui · Indianapolis is 174 mi from Chicago
Premium cabin flights from Chicago to Maui
Premium cabin
2026-11-08
ORD - OGG
First | 1 Stop | 2 left
From 50,000 Pts + $25.6
Premium cabin
2026-11-10
ORD - OGG
First | 1 Stop | 1 left
From 50,000 Pts + $25.6
Premium cabin
2026-11-13
ORD - OGG
First | 1 Stop | 5 left
From 50,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - OGG
First | 1 Stop | 7 left
From 50,000 Pts + $25.6
Premium cabin
2026-11-15
ORD - OGG
First | 1 Stop | 9+ left
From 50,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - OGG
First | 1 Stop | 3 left
From 50,000 Pts + $25.6
Selected hotels for your next stay
Lahaina (United States)
Hyatt Regency Maui Resort and Spa
From 20,000 Pts or $544
Maui, HI (USA)
The Westin Maui Resort & Spa, Ka'anapali
From Pts or $644
Maui, HI (USA)
Sheraton Maui Resort & Spa
From Pts or $764
Frequently Asked Questions
The cheapest route from Chicago to Maui depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Maui.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Maui.
Chicago and Maui are about 4,175 miles (6,719 km) apart in a straight line.
Flying the 4,175-mile straight-line distance takes about 8h 45m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Maui is 4 hours behind Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Maui: Kahului (OGG).
Travelers searching this route also look at other popular routes into Maui, plus the return trip when we track it. Fares and award space change daily.
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