Cheap flights from Chicago to Windward Coast

View AU$320 flight on Wed, 22 Oct. 2025Opens in a new window

Popular airlines from Chicago to Windward Coast

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • Southwest Airlines

    Southwest Airlines

  • United

    United

  • American Airlines

    American Airlines

  • Hawaiian Airlines

    Hawaiian Airlines

  • JetBlue Airways

    JetBlue Airways

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Cheap Flights from Chicago (CHI) to Windward Coast (HNL)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$646 Return, found 3 days ago
AU$646
Return
found 3 days ago
Select American Airlines flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$646 found 3 days ago
Alaska Airlines
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$713 Return, found 3 days ago
AU$713
Return
found 3 days ago
Select Alaska Airlines flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$713 found 3 days ago
Alaska Airlines
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$737 Return, found 3 days ago
AU$737
Return
found 3 days ago
Select Alaska Airlines flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$737 found 3 days ago
Alaska Airlines
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$746 Return, found 3 days ago
AU$746
Return
found 3 days ago
Select Alaska Airlines flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$746 found 3 days ago
Delta
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$790 Return, found 3 days ago
AU$790
Return
found 3 days ago
Select Delta flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$790 found 3 days ago
United
Sat, 6 Dec. - Fri, 12 Dec.
ORD
Chicago
HNL
Oahu
AU$831 Return, found 3 days ago
AU$831
Return
found 3 days ago
Select United flight, departing Sat, 6 Dec. from Chicago to Oahu, returning Fri, 12 Dec., priced at AU$831 found 3 days ago

Find the cheapest month to fly from Chicago (CHI) to Honolulu (HNL)

January is typically the cheapest month to fly

From AU$614 - AU$1,110 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.