$141 Cheap flight deals from Chicago (CHI) to Kihei (OGG)

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This Weekend's Flight Deals from Chicago to Kihei

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Dec 12 - Sat, Dec 13
ORD
O'Hare Intl.
OGG
Kahului
$668 Roundtrip, found 3 days ago
$668
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Dec 12 from O'Hare Intl. to Kahului, returning Sat, Dec 13, priced at $668 found 3 days ago
Fri, Dec 12 - Wed, Dec 17
MDW
Midway Intl.
OGG
Kahului
$780 Roundtrip, found 3 days ago
$780
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Dec 12 from Midway Intl. to Kahului, returning Wed, Dec 17, priced at $780 found 3 days ago

Airfares from $141 One Way, $280 Round Trip from Chicago to Kihei

Prices starting at $280 for return flights and $141 for one-way flights to Kihei were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 18 - Tue, Feb 24
ORD
Chicago
OGG
Maui
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Chicago to Maui, returning Tue, Feb 24, priced at $280 found 2 days ago
Tue, Jan 27 - Tue, Feb 3
ORD
Chicago
OGG
Maui
$282 Roundtrip, found 3 days ago
$282
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Jan 27 from Chicago to Maui, returning Tue, Feb 3, priced at $282 found 3 days ago
Wed, Apr 29 - Wed, May 6
MDW
Chicago
OGG
Maui
$282 Roundtrip, found 5 days ago
$282
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Chicago to Maui, returning Wed, May 6, priced at $282 found 5 days ago
Mon, Jan 26 - Tue, Feb 3
MDW
Chicago
OGG
Maui
$407 Roundtrip, found 4 days ago
$407
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Jan 26 from Chicago to Maui, returning Tue, Feb 3, priced at $407 found 4 days ago
Wed, Feb 18 - Tue, Feb 24
ORD
Chicago
OGG
Maui
$421 Roundtrip, found 2 days ago
$421
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Feb 18 from Chicago to Maui, returning Tue, Feb 24, priced at $421 found 2 days ago

Kihei economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui
3.0-star property

The Gardens at West Maui

8.4/10 Very Good! (512 reviews)

Jan 15 - Jan 21

6 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,821, price is now $1,147 per person
$1,147
per person
found 1 day ago
The perfect location to be near Napili Bay and the Kapalua trail.

Reviewed on Jun 5, 2025

Sands of Kahana
3.0-star property

Sands of Kahana

8.2/10 Very Good! (453 reviews)

Jan 15 - Jan 21

6 night stay

Chicago (CHI) to Kahului (OGG)

American Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,218, price is now $2,465 per person
$2,465
per person
found 1 day ago
Sands of Kahana met all of the requirements or me.

Reviewed on Sep 26, 2024

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

9/10 Wonderful! (1,465 reviews)

Jan 15 - Jan 21

6 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,826, price is now $1,687 per person
$1,687
per person
found 1 day ago
The Outrigger was an amazing place to stay. We walked out the door and to the beach about 100 yards away. We went snorkeling right off the beach and saw turtles, and so many beautiful fish and coral. The people who ran the Outrigger had many complimentary, fun things to do at the hotel every day, like weaving baskets, hula dancing lessons, and learning to play different instruments. All of the people working there were very friendly and helpful. If we have the chance to go back to Maui, we would definitely stay there again.

Reviewed on Jun 16, 2025

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More About Flying To Kihei from Chicago

Route Information for Flights from Chicago to Kihei

Origin Airport IATA Code
CHI
Destination Airport IATA Code
OGG
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Kihei

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.