$195 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, Nov 14 - Thu, Dec 4
ORD
O'Hare Intl.
LIH
Lihue
$449 Roundtrip, found 6 hours ago
$449
Roundtrip
found 6 hours ago
Select Hawaiian Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to Lihue, returning Thu, Dec 4, priced at $449 found 6 hours ago

Airfares from $195 One Way, $369 Round Trip from Chicago to Koloa

Prices starting at $369 for return flights and $195 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, Feb 10 - Tue, Feb 17
ORD
Chicago
LIH
Kauai
$369 Roundtrip, found 6 days ago
$369
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Feb 10 from Chicago to Kauai, returning Tue, Feb 17, priced at $369 found 6 days ago
Mon, Jan 19 - Tue, Jan 27
ORD
Chicago
LIH
Kauai
$373 Roundtrip, found 6 days ago
$373
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Jan 19 from Chicago to Kauai, returning Tue, Jan 27, priced at $373 found 6 days ago
Mon, Jan 19 - Tue, Jan 27
ORD
Chicago
LIH
Kauai
$379 Roundtrip, found 6 days ago
$379
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Mon, Jan 19 from Chicago to Kauai, returning Tue, Jan 27, priced at $379 found 6 days ago
Tue, Jan 20 - Wed, Feb 4
ORD
Chicago
LIH
Kauai
$381 Roundtrip, found 6 hours ago
$381
Roundtrip
found 6 hours ago
Select Hawaiian Airlines flight, departing Tue, Jan 20 from Chicago to Kauai, returning Wed, Feb 4, priced at $381 found 6 hours ago
Sun, Feb 8 - Mon, Feb 16
ORD
Chicago
LIH
Kauai
$383 Roundtrip, found 1 hour ago
$383
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Feb 8 from Chicago to Kauai, returning Mon, Feb 16, priced at $383 found 1 hour ago

Koloa economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,002 reviews)

Dec 12 - Dec 16

4 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,035, price is now $1,424 per person
$1,424
per person
found 16 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

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (253 reviews)

Dec 12 - Dec 16

4 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,299, price is now $2,445 per person
$2,445
per person
found 16 hours ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

Club Wyndham Shearwater
3.5-star property

Club Wyndham Shearwater

8.8/10 Excellent! (122 reviews)

Dec 12 - Dec 16

4 night stay

Chicago (CHI) to Lihue (LIH)

American Airlines • Non-stop • Coach

Lihue (LIH) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $2,018, price is now $1,596 per person
$1,596
per person
found 16 hours ago
Club Wyndham Sheerwater is beautiful! The condo was well kept, beds were comfortable and the service was top notch! I will be staying here again in the future.

Reviewed on Apr 23, 2025

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Koloa first class flight packages

Price found within the past 48 hours. Click for updated prices.
Ko'a Kea Resort on Po'ipu Beach
4.5-star property

Ko'a Kea Resort on Po'ipu Beach

9.4/10 Exceptional! (1,002 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop • FirstClass

Lihue (LIH) to Chicago (ORD)

Alaska Airlines • Non-stop • FirstClass
Price was $10,670, price is now $8,930 per person
$8,930
per person
found 1 hour 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

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (253 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop • FirstClass

Lihue (LIH) to Chicago (ORD)

Alaska Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $22,239, price is now $16,003 per person
$16,003
per person
found 1 hour ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

Timbers Kauai Ocean Club & Residences
5.0-star property

Timbers Kauai Ocean Club & Residences

10/10 Exceptional! (32 reviews)

Dec 27 - Jan 3

7 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop • FirstClass

Lihue (LIH) to Chicago (ORD)

Alaska Airlines • Non-stop • FirstClass
Price was $19,396, price is now $16,295 per person
$16,295
per person
found 1 hour ago
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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.