Flights to Upcountry Maui from Chicago - ￥33,690

View ￥33,690 flight on Sat, Aug 23, 2025Opens in a new window

Popular airlines from Chicago to Upcountry Maui

  • Peach

    Peach

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    All Nippon Airways

  • Japan Airlines

    Japan Airlines

  • Jetstar Japan

    Jetstar Japan

  • Solaseed Air

    Solaseed Air

  • STARFLYER

    STARFLYER

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Cheap Flights from Chicago to Upcountry Maui (CHI-OGG)

Prices were available within the past 7 days and start at ￥33,690 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 4 days ago
￥84,430
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥84,430 found 4 days ago
United
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥86,400 Roundtrip, found 4 days ago
￥86,400
Roundtrip
found 4 days ago
Select United flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥86,400 found 4 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥86,600 Roundtrip, found 4 days ago
￥86,600
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥86,600 found 4 days ago
United
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥87,110 Roundtrip, found 4 days ago
￥87,110
Roundtrip
found 4 days ago
Select United flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥87,110 found 4 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥87,360 Roundtrip, found 4 days ago
￥87,360
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥87,360 found 4 days ago
American Airlines
Mon, Aug 11 - Mon, Aug 25
ORD
Chicago
OGG
Maui
￥90,930 Roundtrip, found 4 days ago
￥90,930
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Maui, returning Mon, Aug 25, priced at ￥90,930 found 4 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.