$251 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.

Sun, Apr 5 - Sat, Apr 11
ORD
O'Hare Intl.
OGG
Kahului
$1,329 Roundtrip, found 3 days ago
$1,329
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sun, Apr 5 from O'Hare Intl. to Kahului, returning Sat, Apr 11, priced at $1,329 found 3 days ago

Airfares from $251 One Way, $491 Round Trip from Chicago to Makawao

Prices starting at $491 for return flights and $251 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, May 6 - Mon, May 11
ORD
Chicago
OGG
Maui
$491 Roundtrip, found 5 days ago
$491
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 6 from Chicago to Maui, returning Mon, May 11, priced at $491 found 5 days ago
Mon, May 4 - Mon, May 11
ORD
Chicago
OGG
Maui
$495 Roundtrip, found 22 hours ago
$495
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Mon, May 4 from Chicago to Maui, returning Mon, May 11, priced at $495 found 22 hours ago
Mon, May 4 - Tue, May 12
ORD
Chicago
OGG
Maui
$500 Roundtrip, found 21 hours ago
$500
Roundtrip
found 21 hours ago
Select Alaska Airlines flight, departing Mon, May 4 from Chicago to Maui, returning Tue, May 12, priced at $500 found 21 hours ago
Thu, Apr 23 - Fri, Apr 24
ORD
Chicago
OGG
Maui
$522 Roundtrip, found 1 day ago
$522
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Apr 23 from Chicago to Maui, returning Fri, Apr 24, priced at $522 found 1 day ago
Tue, Sep 22 - Tue, Sep 29
MDW
Chicago
OGG
Maui
$554 Roundtrip, found 6 days ago
$554
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Sep 22 from Chicago to Maui, returning Tue, Sep 29, priced at $554 found 6 days ago

Makawao economy flight packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Honua Kai Resort & Spa
4.5-star property

OUTRIGGER Honua Kai Resort & Spa

8.8/10 Excellent! (2,929 reviews)

Apr 30 - May 6

6 night stay

Chicago (CHI) to Kahului (OGG)

American Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,378, price is now $1,615 per person
$1,615
per person
found 23 hours ago
Beautiful resort with great amenities. We loved having the condo space and kitchen so we could have meals in the condo or go out if we wanted to. Pools were great, beach was amazing. The only thing I will say is the lighting in the condo was very dim. Those of us with eyes over 40 could use more light at night.

Reviewed on Mar 14, 2025

The Whaler Resort Kaanapali Beach
4.0-star property

The Whaler Resort Kaanapali Beach

9.6/10 Exceptional! (367 reviews)

Apr 30 - May 6

6 night stay

Chicago (CHI) to Kahului (OGG)

American Airlines • Non-stop • Coach

Kahului (OGG) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,697, price is now $1,892 per person
$1,892
per person
found 23 hours ago
Kapalua Villas Maui
4.0-star property

Kapalua Villas Maui

8.6/10 Excellent! (975 reviews)

May 7 - May 14

7 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,257, price is now $1,623 per person
$1,623
per person
found 1 hour ago
Beautiful location. Would have been nice to have some chairs for the beach or towels provided.

Reviewed on May 30, 2025

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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.