$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 16 hours ago
$774
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Midway Intl. to Kahului, returning Thu, Nov 27, priced at $774 found 16 hours ago
Sat, Nov 22 - Thu, Nov 27
ORD
O'Hare Intl.
OGG
Kahului
$784 Roundtrip, found 8 hours ago
$784
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Sat, Nov 22 from O'Hare Intl. to Kahului, returning Thu, Nov 27, priced at $784 found 8 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 15 hours ago
$388
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 9, priced at $388 found 15 hours ago
Tue, Feb 3 - Wed, Feb 11
ORD
Chicago
OGG
Maui
$451 Roundtrip, found 17 hours ago
$451
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Feb 3 from Chicago to Maui, returning Wed, Feb 11, priced at $451 found 17 hours ago
Tue, Feb 3 - Wed, Feb 11
MDW
Chicago
OGG
Maui
$488 Roundtrip, found 17 hours ago
$488
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Maui, returning Wed, Feb 11, priced at $488 found 17 hours ago
Mon, Dec 8 - Mon, Dec 15
ORD
Chicago
LNY
Lanai
$677 Roundtrip, found 19 hours ago
$677
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Mon, Dec 8 from Chicago to Lanai, returning Mon, Dec 15, priced at $677 found 19 hours ago
Thu, Feb 5 - Thu, Feb 12
ORD
Chicago
OGG
Maui
$814 Roundtrip, found 17 hours ago
$814
Roundtrip
found 17 hours ago
Select United flight, departing Thu, Feb 5 from Chicago to Maui, returning Thu, Feb 12, priced at $814 found 17 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

16.4/10 Exceptional! (812 reviews)

Dec 24 - Dec 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Southwest Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

United • Non-stop • Coach
Save 100% on your flight
Price was $2,767, price is now $1,694 per person
$1,694
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

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

18/10 Exceptional! (1,458 reviews)

Dec 24 - Dec 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Southwest Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

United • Non-stop • Coach
Save 100% on your flight
Price was $3,947, price is now $2,042 per person
$2,042
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

Royal Lahaina Resort & Bungalows
4.0-star property

Royal Lahaina Resort & Bungalows

16.8/10 Exceptional! (1,542 reviews)

Dec 24 - Dec 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Southwest Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

United • Non-stop • Coach
Save 100% on your flight
Price was $3,629, price is now $1,936 per person
$1,936
per person
found 1 day ago
Good view. Average service. Housekeeping is every other day. Restricted checking in and out policy.

Reviewed on Jul 30, 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.