$192 Cheap flight deals from Chicago (CHI) to East Maui (OGG)

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This Weekend's Flight Deals from Chicago to East 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, Jan 30 - Fri, Feb 6
ORD
O'Hare Intl.
OGG
Kahului
$578 Roundtrip, found 6 days ago
$578
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Fri, Jan 30 from O'Hare Intl. to Kahului, returning Fri, Feb 6, priced at $578 found 6 days ago
Fri, Jan 30 - Wed, Feb 11
ORD
O'Hare Intl.
JHM
West Maui
$856 Roundtrip, found 3 days ago
$856
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Jan 30 from O'Hare Intl. to West Maui, returning Wed, Feb 11, priced at $856 found 3 days ago

Airfares from $192 One Way, $377 Round Trip from Chicago to East Maui

Prices starting at $377 for return flights and $192 for one-way flights to East 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.

Wed, May 6 - Tue, May 12
ORD
Chicago
OGG
Maui
$377 Roundtrip, found 2 days ago
$377
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, May 6 from Chicago to Maui, returning Tue, May 12, priced at $377 found 2 days ago
Wed, May 6 - Tue, May 12
ORD
Chicago
OGG
Maui
$402 Roundtrip, found 2 days ago
$402
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, May 6 from Chicago to Maui, returning Tue, May 12, priced at $402 found 2 days ago
Tue, Apr 7 - Thu, Apr 16
ORD
Chicago
OGG
Maui
$402 Roundtrip, found 6 hours ago
$402
Roundtrip
found 6 hours ago
Select Hawaiian Airlines flight, departing Tue, Apr 7 from Chicago to Maui, returning Thu, Apr 16, priced at $402 found 6 hours ago
Mon, Feb 23 - Tue, Mar 3
ORD
Chicago
OGG
Maui
$422 Roundtrip, found 1 day ago
$422
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Feb 23 from Chicago to Maui, returning Tue, Mar 3, priced at $422 found 1 day ago
Wed, Apr 15 - Mon, Apr 20
MDW
Chicago
OGG
Maui
$461 Roundtrip, found 4 days ago
$461
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Apr 15 from Chicago to Maui, returning Mon, Apr 20, priced at $461 found 4 days ago

East Maui economy flight packages

Price found within the past 48 hours. Click for updated prices.
Royal Kahana Maui by OUTRIGGER
3.0-star property

Royal Kahana Maui by OUTRIGGER

8/10 Very Good! (1,394 reviews)

Feb 26 - Mar 4

6 night stay

Chicago (CHI) to Kahului (OGG)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,708, price is now $1,136 per person
$1,136
per person
found 1 day ago
The housewares on site were just what we needed; everything from wine glasses to baking trays. The unit was beautifully decorated. The table on the lanai was the perfect amenity for sunrise coffee & cakes.

Reviewed on Oct 23, 2025

Kahana Beach Vacation Club
3.0-star property

Kahana Beach Vacation Club

8.4/10 Very Good! (744 reviews)

Mar 14 - Mar 21

7 night stay

Chicago (CHI) to Kahului (OGG)

United • Coach

Kahului (OGG) to Chicago (CHI)

Alaska Airlines • Coach
Price was $3,540, price is now $2,273 per person
$2,273
per person
found 1 day ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.

Reviewed on Sep 7, 2025

Hono Koa Vacation Club
3.0-star property

Hono Koa Vacation Club

8.6/10 Excellent! (203 reviews)

Mar 4 - Mar 11

7 night stay

Chicago (ORD) to Kahului (OGG)

Alaska Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,412, price is now $2,418 per person
$2,418
per person
found 1 day ago
Check in was great! Lady at the office was friendly and very accommodating in us checking out early. The unit was clean and had everything we needed! I would come again!

Reviewed on Mar 8, 2023

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East Maui first class 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

8.4/10 Very Good! (744 reviews)

Mar 16 - Mar 22

6 night stay

Chicago (ORD) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $3,740, price is now $2,900 per person
$2,900
per person
found 5 hours ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.

Reviewed on Sep 7, 2025

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

9/10 Wonderful! (1,465 reviews)

Mar 16 - Mar 22

6 night stay

Chicago (ORD) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $4,398, price is now $3,470 per person
$3,470
per person
found 5 hours 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

The Whaler Resort Kaanapali Beach
4.0-star property

The Whaler Resort Kaanapali Beach

9.6/10 Exceptional! (292 reviews)

Mar 16 - Mar 22

6 night stay

Chicago (ORD) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $4,818, price is now $3,844 per person
$3,844
per person
found 5 hours ago
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More About Flying To East Maui from Chicago

Route Information for Flights from Chicago to East Maui

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

Chicago to East 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.