$235 Cheap flight deals from Chicago (CHI) to Makawao (OGG)

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This Weekend's Flight Deals from Chicago to Makawao

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, Sep 19 - Tue, Sep 22
ORD
O'Hare Intl.
OGG
Kahului
$607 Roundtrip, found 3 days ago
$607
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sat, Sep 19 from O'Hare Intl. to Kahului, returning Tue, Sep 22, priced at $607 found 3 days ago

Airfares from $235 One Way, $462 Round Trip from Chicago to Makawao

Prices starting at $462 for return flights and $235 for one-way flights to Makawao 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, Oct 28 - Tue, Nov 10
ORD
Chicago
OGG
Maui
$462 Roundtrip, found 4 days ago
$462
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Oct 28 from Chicago to Maui, returning Tue, Nov 10, priced at $462 found 4 days ago
Sat, Dec 5 - Tue, Dec 8
ORD
Chicago
OGG
Maui
$466 Roundtrip, found 6 days ago
$466
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Dec 5 from Chicago to Maui, returning Tue, Dec 8, priced at $466 found 6 days ago
Fri, Feb 5 - Fri, Feb 12
ORD
Chicago
OGG
Maui
$469 Roundtrip, found 6 days ago
$469
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Feb 5 from Chicago to Maui, returning Fri, Feb 12, priced at $469 found 6 days ago
Sat, Dec 5 - Tue, Dec 8
ORD
Chicago
OGG
Maui
$475 Roundtrip, found 6 days ago
$475
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Dec 5 from Chicago to Maui, returning Tue, Dec 8, priced at $475 found 6 days ago
Tue, Oct 27 - Tue, Nov 3
ORD
Chicago
OGG
Maui
$477 Roundtrip, found 4 days ago
$477
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Tue, Oct 27 from Chicago to Maui, returning Tue, Nov 3, priced at $477 found 4 days ago

Makawao economy flight packages

Price found within the past 48 hours. Click for updated prices.
Gods Peace Of Maui
2.0-star property

Gods Peace Of Maui

8.6/10 Excellent! (143 reviews)

Oct 20 - Oct 28

8 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Price was $1,322, price is now $1,008 per person
$1,008
per person
found 1 day ago
Wonderful people and accommodations!

Reviewed on Sep 3, 2026

Maui Beach Vacation Club
2.5-star property

Maui Beach Vacation Club

8.4/10 Very Good! (937 reviews)

Oct 20 - Oct 28

8 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,929, price is now $1,883 per person
$1,883
per person
found 1 day ago
everything was perfect instead of there was no AC IN ROOM

Reviewed on Sep 14, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
5.0-star property

Hotel Wailea, Relais & Chateaux - Adults Only

9.4/10 Exceptional! (1,000 reviews)

Oct 16 - Oct 19

3 night stay

Chicago (CHI) to Kahului (OGG)

Southwest Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,072, price is now $2,133 per person
$2,133
per person
found 9 hours ago
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

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More About Flying To Makawao from Chicago

Route Information for Flights from Chicago to Makawao

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

Chicago to Makawao

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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.