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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, Jul 24 - Mon, Aug 3

ORD

O'Hare Intl.

OGG

Kahului

$776

Roundtrip

found 14 hours ago

Airfares from $217 One Way, $415 Round Trip from Chicago to Kihei

Prices starting at $415 for return flights and $217 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.

Tue, Jan 12 - Wed, Jan 20

ORD

Chicago

OGG

Maui

$415

Roundtrip

found 1 day ago

Tue, Jan 12 - Wed, Jan 20

ORD

Chicago

OGG

Maui

$434

Roundtrip

found 1 day ago

Tue, Feb 9 - Tue, Feb 16

ORD

Chicago

OGG

Maui

$434

Roundtrip

found 3 days ago

Sun, Oct 4 - Fri, Oct 9

MDW

Chicago

OGG

Maui

$505

Roundtrip

found 1 day ago

Wed, Aug 19 - Thu, Aug 27

ORD

Chicago

HNM

Hana

$832

Roundtrip

found 3 days ago

Kihei economy flight packages

Price found within the past 48 hours. Click for updated prices.

2.5-star property

Maui Beach Vacation Club

8.4/10 Very Good! (912 reviews)

Aug 24 - Aug 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Non-stop roundtrip • Coach

Save 100% on your flight

$1,265

per person

found 1 day ago

This was a good place to stay with a family and be centrally located. We could cook in our room and used the BBQ a couple times. We enjoyed the pool and hung out there almost every evening after a day exploring. I appreciate the cleanliness of the pool and other community areas. For the money, it’s a solid place to stay. But the quality of the room was lacking. Several things broke while we were there and had clearly been glued together previously to hide a previous break (e.g. handle to the microwave and shower door). The sofa bead was broken and sofa sheets were dirty when we got there. It was quite loud at night sometimes with the windows open; people talking in the walkways woke us up many times. This probably depends where your room is. Overall, I would recommend if you want an affordable place to stay and have a full kitchen, which really was a huge benefit with kids for a week.

Reviewed on Jul 20, 2026

5.0-star property

Hotel Wailea, Relais & Chateaux - Adults Only

9.4/10 Exceptional! (1,001 reviews)

Aug 24 - Aug 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Non-stop roundtrip • Coach

Save 100% on your flight

$2,359

per person

found 1 day ago

The property was beautiful and well maintained. Lush garden spaces. Pool area and loungers being available along with poolside service was great. Room was large and felt very private. Overall quiet property and relaxing stay. Beach picnic excursion was great as well!

Reviewed on Jul 8, 2026

3.5-star property

Mana Kai Maui- Official Onsite Rental

9/10 Wonderful! (1,008 reviews)

Aug 24 - Aug 30

6 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Non-stop roundtrip • Coach

Save 100% on your flight

$1,753

per person

found 1 day ago

We had a great stay! Although the restaurant on the resort is under construction!

Reviewed on Jul 21, 2026

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Kihei first class flight packages

Price found within the past 48 hours. Click for updated prices.

5.0-star property

Grand Wailea Maui, A Waldorf Astoria Resort

8.8/10 Excellent! (1,015 reviews)

Sep 8 - Sep 15

7 night stay

Chicago (ORD) to Kahului (OGG)

American Airlines • Non-stop • FirstClass

Kahului (OGG) to Chicago (ORD)

Delta • Non-stop • FirstClass

$4,784

per person

found 18 hours ago

5.0-star property

Fairmont Kea Lani Maui

9.4/10 Exceptional! (1,003 reviews)

Sep 8 - Sep 15

7 night stay

Chicago (ORD) to Kahului (OGG)

American Airlines • Non-stop • FirstClass

Kahului (OGG) to Chicago (ORD)

Delta • Non-stop • FirstClass

$5,124

per person

found 18 hours ago

We had a nice time and the hotel was nice. It’s definitely fairly lively with kiddos. The adult pool is close to a main restaurant so not a lot of true quiet time anywhere on property. Rooms are spacious, clean and nice verandas. All the restaurants were tasty. The kids slide for those coming with families is definitely a hit. Overall we enjoyed our time but would have liked a few more adult/quiet pool options for reading and relaxing.

Reviewed on Jul 19, 2026

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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.

$217 Cheap flight deals from Chicago (CHI) to Kihei (OGG)

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This Weekend's Flight Deals from Chicago to Kihei

Airfares from $217 One Way, $415 Round Trip from Chicago to Kihei