$191 Cheap flight deals from Chicago (CHI) to Kihei (OGG)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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, Jan 2 - Fri, Jan 9
ORD
O'Hare Intl.
OGG
Kahului
$761 Roundtrip, found 15 hours ago
$761
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Fri, Jan 2 from O'Hare Intl. to Kahului, returning Fri, Jan 9, priced at $761 found 15 hours ago
Fri, Jan 2 - Fri, Jan 9
MDW
Midway Intl.
OGG
Kahului
$763 Roundtrip, found 15 hours ago
$763
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Fri, Jan 2 from Midway Intl. to Kahului, returning Fri, Jan 9, priced at $763 found 15 hours ago
Sun, Jan 4 - Wed, Jan 21
ORD
O'Hare Intl.
JHM
West Maui
$946 Roundtrip, found 22 hours ago
$946
Roundtrip
found 22 hours ago
Select Hawaiian Airlines flight, departing Sun, Jan 4 from O'Hare Intl. to West Maui, returning Wed, Jan 21, priced at $946 found 22 hours ago

Airfares from $191 One Way, $371 Round Trip from Chicago to Kihei

Prices starting at $371 for return flights and $191 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, Apr 14 - Tue, Apr 21
ORD
Chicago
OGG
Maui
$371 Roundtrip, found 1 hour ago
$371
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Apr 14 from Chicago to Maui, returning Tue, Apr 21, priced at $371 found 1 hour ago
Tue, Jan 27 - Tue, Feb 3
ORD
Chicago
OGG
Maui
$414 Roundtrip, found 20 hours ago
$414
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jan 27 from Chicago to Maui, returning Tue, Feb 3, priced at $414 found 20 hours ago
Mon, Feb 23 - Mon, Mar 9
ORD
Chicago
OGG
Maui
$467 Roundtrip, just found
$467
Roundtrip
just found
Select American Airlines flight, departing Mon, Feb 23 from Chicago to Maui, returning Mon, Mar 9, priced at $467 just found
Fri, Jan 30 - Thu, Feb 5
MDW
Chicago
OGG
Maui
$510 Roundtrip, found 2 days ago
$510
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jan 30 from Chicago to Maui, returning Thu, Feb 5, priced at $510 found 2 days ago
Mon, Apr 27 - Wed, May 6
ORD
Chicago
OGG
Maui
$553 Roundtrip, just found
$553
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Apr 27 from Chicago to Maui, returning Wed, May 6, priced at $553 just found

Kihei 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

8.4/10 Very Good! (744 reviews)

Feb 19 - Feb 23

4 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,739, price is now $1,053 per person
$1,053
per person
found 1 day ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.

Reviewed on Sep 7, 2025

Kaanapali Maui at the Eldorado by OUTRIGGER
3.0-star property

Kaanapali Maui at the Eldorado by OUTRIGGER

8.6/10 Excellent! (871 reviews)

Feb 12 - Feb 16

4 night stay

Chicago (CHI) to Kahului (OGG)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,274, price is now $1,300 per person
$1,300
per person
found 1 day ago
There was a issue with bugs

Reviewed on Oct 14, 2025

OUTRIGGER Kaanapali Beach Resort
3.5-star property

OUTRIGGER Kaanapali Beach Resort

9/10 Wonderful! (1,465 reviews)

Feb 8 - Feb 15

7 night stay

Chicago (CHI) to Kahului (OGG)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,940, price is now $1,831 per person
$1,831
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

Don't see what you're looking for?
See all available trips from Chicago to Kihei
View all trips

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

Book your trip through Orbitz for the best deals on Chicago to Kihei flights. With our cutting-edge mobile tools, getting fantastic savings on international or domestic flights or updates on your flight status has never been easier. Find your low-priced flights from Chicago to Kihei today with Orbitz.

Frequent Flyer Rewards

If you are a member of a frequent flyer program, Orbitz will ensure you get points or miles for your qualifying Chicago to Kihei flights. Just provide your frequent flyer number or your loyalty program number when booking your flight online with Orbtiz.com.

Flight Deals on the Go

Never miss out on great savings! Get fantastic deals on flights from Chicago to Kihei on your mobile device with our apps for iPhone, Android, and iPad, or use your mobile Web browser to access m.orbitz.com. Find big discounts on the hotels you want to stay at to go along with your Chicago to Kihei flights. The app even gives you information for baggage claim and other important flight details.

Free Flight Alerts

With Orbitz, not do you get amazing low-cost deals on Chicago to Kihei flights, but we can send you flight alerts to your mobile phone or email. Instantly learn about delays to your flights from Chicago to Kihei, so you can plan ahead and make different travel arrangements if you need to.

Guaranteed low prices for Chicago to Kihei flights makes Orbitz the perfect online budget travel source.

More Destinations

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.