Flights from Chicago to Maui

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.

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$465 Roundtrip, found 1 day ago

$465

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $465 found 1 day ago

Thu, Nov 27 - Wed, Dec 3

ORD

O'Hare Intl.

OGG

Kahului

$485 Roundtrip, found 2 days ago

$485

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Nov 27 from O'Hare Intl. to Kahului, returning Wed, Dec 3, priced at $485 found 2 days ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$494 Roundtrip, found 1 day ago

$494

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $494 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$499 Roundtrip, found 1 day ago

$499

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $499 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$504 Roundtrip, found 1 day ago

$504

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $504 found 1 day ago

Thu, Nov 27 - Tue, Dec 2

ORD

O'Hare Intl.

OGG

Kahului

$530 Roundtrip, found 2 days ago

$530

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, Nov 27 from O'Hare Intl. to Kahului, returning Tue, Dec 2, priced at $530 found 2 days ago

Fri, Nov 28 - Wed, Dec 3

ORD

O'Hare Intl.

OGG

Kahului

$544 Roundtrip, found 2 days ago

$544

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Nov 28 from O'Hare Intl. to Kahului, returning Wed, Dec 3, priced at $544 found 2 days ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$551 Roundtrip, found 1 day ago

$551

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $551 found 1 day ago

Mon, Nov 24 - Wed, Dec 3

ORD

O'Hare Intl.

OGG

Kahului

$553 Roundtrip, found 2 days ago

$553

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Mon, Nov 24 from O'Hare Intl. to Kahului, returning Wed, Dec 3, priced at $553 found 2 days ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$558 Roundtrip, found 1 day ago

$558

Roundtrip

found 1 day ago

Select United flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $558 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$564 Roundtrip, found 1 day ago

$564

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $564 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$569 Roundtrip, found 1 day ago

$569

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $569 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$574 Roundtrip, found 1 day ago

$574

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $574 found 1 day ago

Thu, Nov 27 - Mon, Dec 1

ORD

O'Hare Intl.

OGG

Kahului

$579 Roundtrip, found 2 days ago

$579

Roundtrip

found 2 days ago

Select Hawaiian Airlines flight, departing Thu, Nov 27 from O'Hare Intl. to Kahului, returning Mon, Dec 1, priced at $579 found 2 days ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$582 Roundtrip, found 1 day ago

$582

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $582 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$585 Roundtrip, found 1 day ago

$585

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $585 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$593 Roundtrip, found 1 day ago

$593

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $593 found 1 day ago

Mon, Aug 18 - Mon, Aug 25

ORD

O'Hare Intl.

OGG

Kahului

$593 Roundtrip, found 1 day ago

$593

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Kahului, returning Mon, Aug 25, priced at $593 found 1 day ago

Sat, May 9 - Sun, May 17

ORD

O'Hare Intl.

OGG

Kahului

$824 Roundtrip, found 1 day ago

$824

Roundtrip

found 1 day ago

Select United flight, departing Sat, May 9 from O'Hare Intl. to Kahului, returning Sun, May 17, priced at $824 found 1 day ago

Mon, Nov 24 - Sat, Nov 29

MDW

Midway Intl.

OGG

Kahului

$2,119 Roundtrip, found 5 days ago

$2,119

Roundtrip

found 5 days ago

Select Delta flight, departing Mon, Nov 24 from Midway Intl. to Kahului, returning Sat, Nov 29, priced at $2,119 found 5 days ago