Flights to Maui from Chicago - $184

View $184 flight on Tue, Nov 4, 2025Opens in a new window

Popular airlines from Chicago to Maui

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

  • American Airlines

    American Airlines

  • Southwest Airlines

    Southwest Airlines

  • Hawaiian Airlines

    Hawaiian Airlines

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Cheap Flights from Chicago to Maui (CHI-OGG)

Prices were available within the past 7 days and start at $184 for one-way flights and $365 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Bargain Flight
Wed, Oct 15 - Tue, Oct 21
ORD
Chicago
OGG
Maui
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Oct 15 from Chicago to Maui, returning Tue, Oct 21, priced at $365 found 1 day ago
Alaska Airlines
Tue, Oct 14 - Tue, Oct 21
ORD
Chicago
OGG
Maui
$367 Roundtrip, found 2 hours ago
$367
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Tue, Oct 14 from Chicago to Maui, returning Tue, Oct 21, priced at $367 found 2 hours ago
Southwest Airlines
Fri, Sep 5 - Mon, Sep 8
MDW
Chicago
OGG
Maui
$409 Roundtrip, found 5 days ago
$409
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Sep 5 from Chicago to Maui, returning Mon, Sep 8, priced at $409 found 5 days ago
Delta
Fri, Sep 5 - Wed, Sep 10
ORD
Chicago
OGG
Maui
$409 Roundtrip, just found
$409
Roundtrip
just found
Select Delta flight, departing Fri, Sep 5 from Chicago to Maui, returning Wed, Sep 10, priced at $409 just found
American Airlines
Mon, Jan 5 - Mon, Jan 12
ORD
Chicago
OGG
Maui
$409 Roundtrip, just found
$409
Roundtrip
just found
Select American Airlines flight, departing Mon, Jan 5 from Chicago to Maui, returning Mon, Jan 12, priced at $409 just found
Hawaiian Airlines
Thu, Sep 4 - Thu, Sep 4
ORD
Chicago
OGG
Maui
$482 Roundtrip, found 2 hours ago
$482
Roundtrip
found 2 hours ago
Select Hawaiian Airlines flight, departing Thu, Sep 4 from Chicago to Maui, returning Thu, Sep 4, priced at $482 found 2 hours ago

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

September is typically the cheapest month to fly

From $334 - $574 per traveler.

Graph displaying average flight prices per month

*Available to One Key members.