Cheap Flights from Chicago to Upcountry Maui

View €352 flight on Sat, 9 Aug 2025Opens in a new window

Popular airlines from Chicago to Upcountry Maui

  • Aer Lingus

    Aer Lingus

  • Lufthansa

    Lufthansa

  • British Airways

    British Airways

  • Turkish Airlines

    Turkish Airlines

  • American Airlines

    American Airlines

  • Air Serbia

    Air Serbia

  • Swiss International Air Lines

    Swiss International Air Lines

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

Prices were available within the past 7 days and start at €352 for one-way flights and €906 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€906 Return, found 3 days ago
€906
Return
found 3 days ago
Select Delta flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €906 found 3 days ago
Delta
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€914 Return, found 3 days ago
€914
Return
found 3 days ago
Select Delta flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €914 found 3 days ago
Delta
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€918 Return, found 3 days ago
€918
Return
found 3 days ago
Select Delta flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €918 found 3 days ago
American Airlines
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€957 Return, found 3 days ago
€957
Return
found 3 days ago
Select American Airlines flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €957 found 3 days ago
Alaska Airlines
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€988 Return, found 3 days ago
€988
Return
found 3 days ago
Select Alaska Airlines flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €988 found 3 days ago
United
Sat, 5 Jul - Sat, 12 Jul
ORD
Chicago
OGG
Maui
€1,041 Return, found 3 days ago
€1,041
Return
found 3 days ago
Select United flight, departing Sat, 5 Jul from Chicago to Maui, returning Sat, 12 Jul, priced at €1,041 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 €292 - €504 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.