$188 Cheap flight deals from Chicago (CHI) to Koloa (LIH)

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Airfares from $188 One Way, $410 Round Trip from Chicago to Koloa

Prices starting at $410 for return flights and $188 for one-way flights to Koloa 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, Mar 9 - Wed, Mar 18
ORD
Chicago
LIH
Kauai
$410 Roundtrip, found 23 hours ago
$410
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Mon, Mar 9 from Chicago to Kauai, returning Wed, Mar 18, priced at $410 found 23 hours ago
Tue, May 5 - Tue, May 19
ORD
Chicago
LIH
Kauai
$415 Roundtrip, found 12 hours ago
$415
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Tue, May 5 from Chicago to Kauai, returning Tue, May 19, priced at $415 found 12 hours ago
Tue, May 5 - Tue, May 19
ORD
Chicago
LIH
Kauai
$419 Roundtrip, found 12 hours ago
$419
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, May 5 from Chicago to Kauai, returning Tue, May 19, priced at $419 found 12 hours ago
Tue, May 5 - Tue, May 19
ORD
Chicago
LIH
Kauai
$420 Roundtrip, found 12 hours ago
$420
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, May 5 from Chicago to Kauai, returning Tue, May 19, priced at $420 found 12 hours ago
Tue, May 5 - Tue, May 19
ORD
Chicago
LIH
Kauai
$422 Roundtrip, found 12 hours ago
$422
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, May 5 from Chicago to Kauai, returning Tue, May 19, priced at $422 found 12 hours ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Waipouli Beach Resorts & Spa Kauai by OUTRIGGER
4.0-star property

Waipouli Beach Resorts & Spa Kauai by OUTRIGGER

8.8/10 Excellent! (1,002 reviews)

Apr 2 - Apr 6

4 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $2,279, price is now $1,676 per person
$1,676
per person
found 1 day ago
We will liked the condo and how it was layed out and it was convenient to the pool/ocean/parking/etc. I wish there would have been more conveniences in the condo itself (examples: hair dryer, pool toys, cooler, more pans & accessories in the kitchen). We had a great time and loved how quiet and safe it was!

Reviewed on Jan 5, 2026

Grand Hyatt Kauai Resort and Spa
4.5-star property

Grand Hyatt Kauai Resort and Spa

9.4/10 Exceptional! (1,005 reviews)

Apr 2 - Apr 6

4 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $3,120, price is now $2,261 per person
$2,261
per person
found 1 day ago
The staff here are outstanding (especially Victor at the Front Desk!); they make you feel welcome, relaxed and taken care of. Photos do not do the property justice as not only is it gorgeous but peaceful, and you can hear the waves from just about anywhere. The rooms are spacious, comfortable and clean. The in-room coffee maker makes a nice cup of coffee - perfect for relaxing on the lanai. Make sure you sign up for the classes before arrival as they will enhance your experience. This resort is a true gem, and the only place I stay when visiting Kauai.

Reviewed on Dec 17, 2025

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (275 reviews)

Apr 2 - Apr 6

4 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

American Airlines • Non-stop • Coach
Price was $5,666, price is now $4,375 per person
$4,375
per person
found 1 day ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

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More About Flying To Koloa from Chicago

Route Information for Flights from Chicago to Koloa

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

Chicago to Koloa

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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.