$192 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.

Sun, Dec 7 - Sun, Dec 21
ORD
O'Hare Intl.
OGG
Kahului
$634 Roundtrip, found 3 hours ago
$634
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Sun, Dec 7 from O'Hare Intl. to Kahului, returning Sun, Dec 21, priced at $634 found 3 hours ago

Airfares from $192 One Way, $373 Round Trip from Chicago to Kihei

Prices starting at $373 for return flights and $192 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.

Mon, Feb 23 - Mon, Mar 9
ORD
Chicago
OGG
Maui
$373 Roundtrip, found 20 hours ago
$373
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 9, priced at $373 found 20 hours ago
Tue, Feb 3 - Sun, Feb 8
ORD
Chicago
OGG
Maui
$381 Roundtrip, found 5 days ago
$381
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 3 from Chicago to Maui, returning Sun, Feb 8, priced at $381 found 5 days ago
Wed, Feb 25 - Wed, Mar 4
ORD
Chicago
OGG
Maui
$382 Roundtrip, found 5 days ago
$382
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Feb 25 from Chicago to Maui, returning Wed, Mar 4, priced at $382 found 5 days ago
Mon, Feb 23 - Mon, Mar 2
ORD
Chicago
OGG
Maui
$445 Roundtrip, found 7 hours ago
$445
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 2, priced at $445 found 7 hours ago
Tue, Feb 3 - Wed, Feb 11
MDW
Chicago
OGG
Maui
$463 Roundtrip, found 8 hours ago
$463
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Feb 3 from Chicago to Maui, returning Wed, Feb 11, priced at $463 found 8 hours ago

Kihei economy flight packages

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club
2.5-star property

Maui Beach Vacation Club

8.2/10 Very Good! (814 reviews)

Jan 13 - Jan 19

6 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,809, price is now $1,073 per person
$1,073
per person
found 1 day ago
We like the view of the ocean & close proximity to the beach. Customer service is excellent & friendly; however, the room had no AC to regulate the heat & humidity. Overall, it’s a decent hotel for our budget.

Reviewed on Aug 21, 2025

Sands of Kahana
3.0-star property

Sands of Kahana

8.2/10 Very Good! (453 reviews)

Jan 17 - Jan 24

7 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $4,795, price is now $2,367 per person
$2,367
per person
found 8 hours ago
Sands of Kahana met all of the requirements or me.

Reviewed on Sep 26, 2024

Maui Banyan Vacation Club
3.0-star property

Maui Banyan Vacation Club

8/10 Very Good! (351 reviews)

Jan 17 - Jan 24

7 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Delta • Non-stop • Coach
Price was $1,974, price is now $1,215 per person
$1,215
per person
found 8 hours ago
Property was exceptionally clean and welcoming. People at the poolside were nice. Pool was never crowded. The room I had was managed by Soliel and was impeccably clean, including the exhaust fan cover in the bathroom. I have never seen that anywhere before in all my travels. The property was beautiful and having free parking was a great amenity.

Reviewed on Feb 12, 2023

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Kihei first class flight packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

9/10 Wonderful! (1,465 reviews)

Jan 17 - Jan 23

6 night stay

Chicago (MDW) to Kahului (OGG)

Delta • Roundtrip • FirstClass
Price was $5,418, price is now $4,289 per person
$4,289
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

Maui Beach Vacation Club
2.5-star property

Maui Beach Vacation Club

8.2/10 Very Good! (814 reviews)

Jan 17 - Jan 23

6 night stay

Chicago (MDW) to Kahului (OGG)

Delta • Roundtrip • FirstClass
Price was $6,052, price is now $4,448 per person
$4,448
per person
found 1 day ago
We like the view of the ocean & close proximity to the beach. Customer service is excellent & friendly; however, the room had no AC to regulate the heat & humidity. Overall, it’s a decent hotel for our budget.

Reviewed on Aug 21, 2025

Sands of Kahana
3.0-star property

Sands of Kahana

8.2/10 Very Good! (453 reviews)

Jan 17 - Jan 23

6 night stay

Chicago (MDW) to Kahului (OGG)

Delta • Roundtrip • FirstClass
Price was $6,983, price is now $5,216 per person
$5,216
per person
found 1 day ago
Sands of Kahana met all of the requirements or me.

Reviewed on Sep 26, 2024

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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.