$180 Cheap flight deals from Chicago (CHI) to Koloa (LIH)

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This Weekend's Flight Deals from Chicago to Koloa

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, Dec 26 - Fri, Jan 9
MDW
Midway Intl.
LIH
Lihue
$1,124 Roundtrip, found 2 days ago
$1,124
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Dec 26 from Midway Intl. to Lihue, returning Fri, Jan 9, priced at $1,124 found 2 days ago
Sun, Dec 28 - Mon, Jan 5
ORD
O'Hare Intl.
LIH
Lihue
$1,717 Roundtrip, found 21 hours ago
$1,717
Roundtrip
found 21 hours ago
Select Alaska Airlines flight, departing Sun, Dec 28 from O'Hare Intl. to Lihue, returning Mon, Jan 5, priced at $1,717 found 21 hours ago

Airfares from $180 One Way, $353 Round Trip from Chicago to Koloa

Prices starting at $353 for return flights and $180 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.

Tue, Jan 27 - Tue, Feb 3
ORD
Chicago
LIH
Kauai
$353 Roundtrip, found 2 days ago
$353
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Jan 27 from Chicago to Kauai, returning Tue, Feb 3, priced at $353 found 2 days ago
Tue, Jan 20 - Tue, Feb 3
ORD
Chicago
LIH
Kauai
$357 Roundtrip, found 4 days ago
$357
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, Jan 20 from Chicago to Kauai, returning Tue, Feb 3, priced at $357 found 4 days ago
Tue, Feb 3 - Mon, Feb 9
ORD
Chicago
LIH
Kauai
$357 Roundtrip, found 2 days ago
$357
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Feb 3 from Chicago to Kauai, returning Mon, Feb 9, priced at $357 found 2 days ago
Mon, Jan 26 - Tue, Feb 3
ORD
Chicago
LIH
Kauai
$358 Roundtrip, found 4 days ago
$358
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Mon, Jan 26 from Chicago to Kauai, returning Tue, Feb 3, priced at $358 found 4 days ago
Tue, Jan 20 - Mon, Jan 26
ORD
Chicago
LIH
Kauai
$362 Roundtrip, found 5 days ago
$362
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Jan 20 from Chicago to Kauai, returning Mon, Jan 26, priced at $362 found 5 days ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kauaʻi Beach Resort & Spa
4.0-star property

OUTRIGGER Kauaʻi Beach Resort & Spa

8.4/10 Very Good! (1,427 reviews)

Jan 23 - Jan 31

8 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $2,389, price is now $1,526 per person
$1,526
per person
found 1 day ago
This is a beautiful property and we enjoyed our 5 night stay, very much. The staff was lovely, which is so important. Amanda at the pool bar was awesome and deserves recognition for being very aware of our parties needs, everyday! Our housekeepers were sweet and one was always singing quietly, which I loved because it reminded me of my mom. The things I thought could be improved would be the mattresses, the price for self parking and price/quality of some of the food we had at the lounge and the restaurant. Our mattress was very uncomfortable and slanted a bit at the top. We had a few good food items but also a few items that were not great and overpriced, specifically the steak and eggs and the fish and chips. The steak was tough and lacked flavor and I asked if the fish and chips were good abd beer battered and was toldby our waiter they were, which they were not. I received a pile of fries with 2 tiny, breaded fish strips that appeared to be store bought and not tasty at all. Not what I was expecting

Reviewed on Aug 20, 2025

Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,001 reviews)

Jan 23 - Jan 31

8 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $5,968, price is now $3,829 per person
$3,829
per person
found 1 day ago
We loved that we could walk to the beach very easily. There are daily activities like yoga, ukulele lessons, etc. The pool and hot tub were nice especially after a day of hiking or surfing. The staff was great, they gave great recommendation on places to see on the island. There was only 2 downsides, one was how expensive the food at the restaurant is in comparison to other places around the island, including other resort restaurants. Second is that the parking is $40/day unless you park the car along the main road and walk back to the resort, which we were never told and figured out ourselves the second to last day we were there. Nonetheless this is a perfect place if you want a relaxing quiet space to vacation. It does not get rowdy, that’s not the vibe as all.

Reviewed on Mar 26, 2025

Grand Hyatt Kauai Resort and Spa
4.5-star property

Grand Hyatt Kauai Resort and Spa

9.4/10 Exceptional! (1,005 reviews)

Jan 23 - Jan 31

8 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $9,964, price is now $6,415 per person
$6,415
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

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Koloa packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kauaʻi Beach Resort & Spa
4.0-star property

OUTRIGGER Kauaʻi Beach Resort & Spa

8.4/10 Very Good! (1,427 reviews)

Feb 8 - Feb 13

5 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $2,201, price is now $1,566 per person
$1,566
per person
found 18 hours ago
This is a beautiful property and we enjoyed our 5 night stay, very much. The staff was lovely, which is so important. Amanda at the pool bar was awesome and deserves recognition for being very aware of our parties needs, everyday! Our housekeepers were sweet and one was always singing quietly, which I loved because it reminded me of my mom. The things I thought could be improved would be the mattresses, the price for self parking and price/quality of some of the food we had at the lounge and the restaurant. Our mattress was very uncomfortable and slanted a bit at the top. We had a few good food items but also a few items that were not great and overpriced, specifically the steak and eggs and the fish and chips. The steak was tough and lacked flavor and I asked if the fish and chips were good abd beer battered and was toldby our waiter they were, which they were not. I received a pile of fries with 2 tiny, breaded fish strips that appeared to be store bought and not tasty at all. Not what I was expecting

Reviewed on Aug 20, 2025

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (275 reviews)

Feb 8 - Feb 13

5 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $5,031, price is now $3,514 per person
$3,514
per person
found 18 hours ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,001 reviews)

Feb 8 - Feb 13

5 night stay

Chicago (CHI) to Lihue (LIH)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $3,027, price is now $2,182 per person
$2,182
per person
found 18 hours ago
We loved that we could walk to the beach very easily. There are daily activities like yoga, ukulele lessons, etc. The pool and hot tub were nice especially after a day of hiking or surfing. The staff was great, they gave great recommendation on places to see on the island. There was only 2 downsides, one was how expensive the food at the restaurant is in comparison to other places around the island, including other resort restaurants. Second is that the parking is $40/day unless you park the car along the main road and walk back to the resort, which we were never told and figured out ourselves the second to last day we were there. Nonetheless this is a perfect place if you want a relaxing quiet space to vacation. It does not get rowdy, that’s not the vibe as all.

Reviewed on Mar 26, 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.