$190 Cheap flight deals from Chicago (CHI) to Central Maui (OGG)

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This Weekend's Flight Deals from Chicago to Central Maui

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, Nov 21 - Mon, Nov 24
ORD
O'Hare Intl.
OGG
Kahului
$751 Roundtrip, found 2 hours ago
$751
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Fri, Nov 21 from O'Hare Intl. to Kahului, returning Mon, Nov 24, priced at $751 found 2 hours ago

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

Prices starting at $388 for return flights and $190 for one-way flights to Central Maui 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 1 day ago
$388
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 9, priced at $388 found 1 day ago
Mon, Feb 2 - Fri, Feb 6
ORD
Chicago
OGG
Maui
$451 Roundtrip, found 19 hours ago
$451
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Mon, Feb 2 from Chicago to Maui, returning Fri, Feb 6, priced at $451 found 19 hours ago
Tue, Feb 3 - Wed, Feb 11
MDW
Chicago
OGG
Maui
$488 Roundtrip, found 19 hours ago
$488
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Tue, Feb 3 from Chicago to Maui, returning Wed, Feb 11, priced at $488 found 19 hours ago
Mon, Dec 8 - Mon, Dec 15
ORD
Chicago
LNY
Lanai
$677 Roundtrip, found 1 hour ago
$677
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Mon, Dec 8 from Chicago to Lanai, returning Mon, Dec 15, priced at $677 found 1 hour ago
Thu, Feb 5 - Thu, Feb 12
ORD
Chicago
OGG
Maui
$714 Roundtrip, found 1 day ago
$714
Roundtrip
found 1 day ago
Select United flight, departing Thu, Feb 5 from Chicago to Maui, returning Thu, Feb 12, priced at $714 found 1 day ago

Central Maui 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 1 day ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.

Reviewed on Sep 7, 2025

Royal Lahaina Resort & Bungalows
4.0-star property

Royal Lahaina Resort & Bungalows

16.8/10 Exceptional! (1,542 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 $1,673, price is now $1,120 per person
$1,120
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

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

18/10 Exceptional! (1,458 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 $1,738, price is now $1,280 per person
$1,280
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

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More About Flying To Central Maui from Chicago

Route Information for Flights from Chicago to Central Maui

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

Chicago to Central Maui

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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.