Cheap flights from Chicago to Kahului from CA $383

View CA $383 flight on Sat, Mar. 7, 2026Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Chicago (CHI) to Kahului (OGG)

Prices were available within the past 7 days and start at CA $383 for one-way flights and CA $746 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat., Aug. 23 - Sat., Aug. 30
ORD
Chicago
OGG
Maui
CA $746 Roundtrip, found 6 days ago
CA $746
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat., Aug. 23 from Chicago to Maui, returning Sat., Aug. 30, priced at CA $746 found 6 days ago
Hawaiian Airlines
Tue., Sep. 30 - Tue., Oct. 14
ORD
Chicago
OGG
Maui
CA $766 Roundtrip, found 1 day ago
CA $766
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Tue., Sep. 30 from Chicago to Maui, returning Tue., Oct. 14, priced at CA $766 found 1 day ago
American Airlines
Sat., May 17 - Sat., May 24
ORD
Chicago
OGG
Maui
CA $780 Roundtrip, found 1 day ago
CA $780
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat., May 17 from Chicago to Maui, returning Sat., May 24, priced at CA $780 found 1 day ago
Alaska Airlines
Mon., May 26 - Fri., Jun. 6
ORD
Chicago
OGG
Maui
CA $797 Roundtrip, found 6 days ago
CA $797
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon., May 26 from Chicago to Maui, returning Fri., Jun. 6, priced at CA $797 found 6 days ago
Delta
Fri., Oct. 3 - Fri., Oct. 17
ORD
Chicago
OGG
Maui
CA $857 Roundtrip, found 1 day ago
CA $857
Roundtrip
found 1 day ago
Select Delta flight, departing Fri., Oct. 3 from Chicago to Maui, returning Fri., Oct. 17, priced at CA $857 found 1 day ago
United
Fri., Oct. 3 - Fri., Oct. 17
ORD
Chicago
OGG
Maui
CA $1,106 Roundtrip, found 1 day ago
CA $1,106
Roundtrip
found 1 day ago
Select United flight, departing Fri., Oct. 3 from Chicago to Maui, returning Fri., Oct. 17, priced at CA $1,106 found 1 day ago
*Available to Expedia members.