$190 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.

Sat, Nov 22 - Thu, Nov 27
MDW
Midway Intl.
OGG
Kahului
$774 Roundtrip, found 1 day ago
$774
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Midway Intl. to Kahului, returning Thu, Nov 27, priced at $774 found 1 day ago
Sat, Nov 22 - Thu, Nov 27
ORD
O'Hare Intl.
OGG
Kahului
$784 Roundtrip, found 16 hours ago
$784
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Sat, Nov 22 from O'Hare Intl. to Kahului, returning Thu, Nov 27, priced at $784 found 16 hours ago

Airfares from $190 One Way, $388 Round Trip from Chicago to Kihei

Prices starting at $388 for return flights and $190 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
$388 Roundtrip, found 23 hours ago
$388
Roundtrip
found 23 hours ago
Select Delta flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 9, priced at $388 found 23 hours ago
Mon, Apr 27 - Wed, May 6
ORD
Chicago
OGG
Maui
$451 Roundtrip, found 3 hours ago
$451
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Chicago to Maui, returning Wed, May 6, priced at $451 found 3 hours ago
Tue, Feb 3 - Wed, Feb 11
MDW
Chicago
OGG
Maui
$488 Roundtrip, found 1 day ago
$488
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Maui, returning Wed, Feb 11, priced at $488 found 1 day ago
Mon, Dec 8 - Mon, Dec 15
ORD
Chicago
LNY
Lanai
$677 Roundtrip, found 1 day ago
$677
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Dec 8 from Chicago to Lanai, returning Mon, Dec 15, priced at $677 found 1 day ago
Thu, Feb 5 - Thu, Feb 12
ORD
Chicago
OGG
Maui
$814 Roundtrip, found 1 day ago
$814
Roundtrip
found 1 day ago
Select United flight, departing Thu, Feb 5 from Chicago to Maui, returning Thu, Feb 12, priced at $814 found 1 day ago

Kihei economy flight packages

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

Kahana Beach Vacation Club

16.8/10 Exceptional! (741 reviews)

Dec 19 - Dec 23

4 night stay

Chicago (CHI) to Kahului (OGG)

Southwest Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $1,420, price is now $1,049 per person
$1,049
per person
found 24 hours ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.

Reviewed on Sep 7, 2025

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

18/10 Exceptional! (1,458 reviews)

Dec 30 - Jan 6

7 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $3,404, price is now $2,313 per person
$2,313
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

Hono Koa Vacation Club
3.0-star property

Hono Koa Vacation Club

8.6/10 Excellent! (200 reviews)

Jan 3 - Jan 10

7 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,731, price is now $1,997 per person
$1,997
per person
found 2 hours ago
Check in was great! Lady at the office was friendly and very accommodating in us checking out early. The unit was clean and had everything we needed! I would come again!

Reviewed on Mar 8, 2023

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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.