Flights to Maui from Chicago - ￥42,540

View ￥42,540 flight on Mon, Aug 11, 2025Opens in a new window

Popular airlines from Chicago to Maui

  • Peach

    Peach

  • Skymark Airlines

    Skymark Airlines

  • All Nippon Airways

    All Nippon Airways

  • Japan Airlines

    Japan Airlines

  • Jetstar Japan

    Jetstar Japan

  • Solaseed Air

    Solaseed Air

  • STARFLYER

    STARFLYER

  • 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 40% 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 to Maui (CHI-OGG)

Prices were available within the past 7 days and start at ￥42,540 for one-way flights and ￥84,430 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥84,430 Roundtrip, found 3 days ago
￥84,430
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥84,430 found 3 days ago
United
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥86,400 Roundtrip, found 3 days ago
￥86,400
Roundtrip
found 3 days ago
Select United flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥86,400 found 3 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥86,600 Roundtrip, found 3 days ago
￥86,600
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥86,600 found 3 days ago
United
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥87,110 Roundtrip, found 3 days ago
￥87,110
Roundtrip
found 3 days ago
Select United flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥87,110 found 3 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥87,360 Roundtrip, found 3 days ago
￥87,360
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥87,360 found 3 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥90,930 Roundtrip, found 3 days ago
￥90,930
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥90,930 found 3 days ago

Find the cheapest month to fly from Chicago (CHI) to Kahului (OGG)

September is typically the cheapest month to fly

From ￥49,069 - ￥84,761 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.