Flights from Chicago to Olowalu

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 30 - Tue, Oct 7

ORD

O'Hare Intl.

OGG

Kahului

$432 Roundtrip, found 4 hours ago

$432

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Tue, Oct 7, priced at $432 found 4 hours ago

Mon, Sep 29 - Tue, Oct 7

ORD

O'Hare Intl.

OGG

Kahului

$442 Roundtrip, found 4 hours ago

$442

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Tue, Oct 7, priced at $442 found 4 hours ago

Tue, Sep 30 - Mon, Oct 13

ORD

O'Hare Intl.

OGG

Kahului

$446 Roundtrip, found 4 hours ago

$446

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Mon, Oct 13, priced at $446 found 4 hours ago

Wed, Oct 1 - Tue, Oct 7

ORD

O'Hare Intl.

OGG

Kahului

$448 Roundtrip, found 4 hours ago

$448

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Wed, Oct 1 from O'Hare Intl. to Kahului, returning Tue, Oct 7, priced at $448 found 4 hours ago

Mon, Sep 29 - Mon, Oct 13

ORD

O'Hare Intl.

OGG

Kahului

$456 Roundtrip, found 4 hours ago

$456

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Mon, Oct 13, priced at $456 found 4 hours ago

Mon, Sep 29 - Mon, Oct 6

ORD

O'Hare Intl.

OGG

Kahului

$456 Roundtrip, found 4 hours ago

$456

Roundtrip

found 4 hours ago

Select Delta flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Mon, Oct 6, priced at $456 found 4 hours ago

Wed, Oct 1 - Mon, Oct 13

ORD

O'Hare Intl.

OGG

Kahului

$461 Roundtrip, found 4 hours ago

$461

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Wed, Oct 1 from O'Hare Intl. to Kahului, returning Mon, Oct 13, priced at $461 found 4 hours ago

Tue, Sep 30 - Mon, Oct 6

ORD

O'Hare Intl.

OGG

Kahului

$469 Roundtrip, found 4 hours ago

$469

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Mon, Oct 6, priced at $469 found 4 hours ago

Fri, Sep 26 - Mon, Oct 13

ORD

O'Hare Intl.

OGG

Kahului

$471 Roundtrip, found 4 hours ago

$471

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Kahului, returning Mon, Oct 13, priced at $471 found 4 hours ago

Tue, Sep 30 - Thu, Oct 9

ORD

O'Hare Intl.

OGG

Kahului

$471 Roundtrip, found 4 hours ago

$471

Roundtrip

found 4 hours ago

Select Alaska Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Thu, Oct 9, priced at $471 found 4 hours ago

Tue, Sep 30 - Sun, Oct 12

ORD

O'Hare Intl.

OGG

Kahului

$474 Roundtrip, found 4 hours ago

$474

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Sun, Oct 12, priced at $474 found 4 hours ago

Mon, Sep 29 - Thu, Oct 9

ORD

O'Hare Intl.

OGG

Kahului

$481 Roundtrip, found 4 hours ago

$481

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Thu, Oct 9, priced at $481 found 4 hours ago

Sat, Sep 27 - Mon, Oct 6

ORD

O'Hare Intl.

OGG

Kahului

$484 Roundtrip, found 4 hours ago

$484

Roundtrip

found 4 hours ago

Select Delta flight, departing Sat, Sep 27 from O'Hare Intl. to Kahului, returning Mon, Oct 6, priced at $484 found 4 hours ago

Fri, Sep 26 - Wed, Oct 8

ORD

O'Hare Intl.

OGG

Kahului

$485 Roundtrip, found 4 hours ago

$485

Roundtrip

found 4 hours ago

Select Delta flight, departing Fri, Sep 26 from O'Hare Intl. to Kahului, returning Wed, Oct 8, priced at $485 found 4 hours ago

Wed, Oct 1 - Sun, Oct 12

ORD

O'Hare Intl.

OGG

Kahului

$489 Roundtrip, found 4 hours ago

$489

Roundtrip

found 4 hours ago

Select Hawaiian Airlines flight, departing Wed, Oct 1 from O'Hare Intl. to Kahului, returning Sun, Oct 12, priced at $489 found 4 hours ago

Tue, Sep 30 - Fri, Oct 10

ORD

O'Hare Intl.

OGG

Kahului

$490 Roundtrip, found 4 hours ago

$490

Roundtrip

found 4 hours ago

Select Delta flight, departing Tue, Sep 30 from O'Hare Intl. to Kahului, returning Fri, Oct 10, priced at $490 found 4 hours ago

Mon, Sep 29 - Tue, Sep 30

ORD

O'Hare Intl.

OGG

Kahului

$533 Roundtrip, found 4 hours ago

$533

Roundtrip

found 4 hours ago

Select American Airlines flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Tue, Sep 30, priced at $533 found 4 hours ago

Mon, Sep 29 - Tue, Sep 30

ORD

O'Hare Intl.

OGG

Kahului

$567 Roundtrip, found 4 hours ago

$567

Roundtrip

found 4 hours ago

Select United flight, departing Mon, Sep 29 from O'Hare Intl. to Kahului, returning Tue, Sep 30, priced at $567 found 4 hours ago

Fri, Jan 2 - Fri, Jan 9

ORD

O'Hare Intl.

OGG

Kahului

$857 Roundtrip, found 6 days ago

$857

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jan 2 from O'Hare Intl. to Kahului, returning Fri, Jan 9, priced at $857 found 6 days ago

Fri, Jan 2 - Fri, Jan 9

MDW

Midway Intl.

OGG

Kahului

$1,145 Roundtrip, found 6 days ago

$1,145

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jan 2 from Midway Intl. to Kahului, returning Fri, Jan 9, priced at $1,145 found 6 days ago