$195 Cheap flight deals from Chicago (CHI) to North Shore Kauai (LIH)

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This Weekend's Flight Deals from Chicago to North Shore Kauai

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.

Sun, Nov 16 - Thu, Dec 4
ORD
O'Hare Intl.
LIH
Lihue
$453 Roundtrip, found 23 hours ago
$453
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, Nov 16 from O'Hare Intl. to Lihue, returning Thu, Dec 4, priced at $453 found 23 hours ago

Airfares from $195 One Way, $381 Round Trip from Chicago to North Shore Kauai

Prices starting at $381 for return flights and $195 for one-way flights to North Shore Kauai 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 20 - Wed, Feb 4
ORD
Chicago
LIH
Kauai
$381 Roundtrip, found 23 hours ago
$381
Roundtrip
found 23 hours ago
Select Hawaiian Airlines flight, departing Tue, Jan 20 from Chicago to Kauai, returning Wed, Feb 4, priced at $381 found 23 hours ago
Tue, Jan 20 - Tue, Jan 27
ORD
Chicago
LIH
Kauai
$381 Roundtrip, found 5 days ago
$381
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Jan 20 from Chicago to Kauai, returning Tue, Jan 27, priced at $381 found 5 days ago
Wed, Jan 28 - Wed, Feb 4
ORD
Chicago
LIH
Kauai
$382 Roundtrip, found 20 hours ago
$382
Roundtrip
found 20 hours ago
Select Hawaiian Airlines flight, departing Wed, Jan 28 from Chicago to Kauai, returning Wed, Feb 4, priced at $382 found 20 hours ago
Sun, Feb 8 - Mon, Feb 16
ORD
Chicago
LIH
Kauai
$383 Roundtrip, found 18 hours ago
$383
Roundtrip
found 18 hours ago
Select Delta flight, departing Sun, Feb 8 from Chicago to Kauai, returning Mon, Feb 16, priced at $383 found 18 hours ago
Wed, Jan 28 - Sun, Feb 8
ORD
Chicago
LIH
Kauai
$383 Roundtrip, found 23 hours ago
$383
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed, Jan 28 from Chicago to Kauai, returning Sun, Feb 8, priced at $383 found 23 hours ago

North Shore Kauai economy flight packages

Price found within the past 48 hours. Click for updated prices.
Aston at Poipu Kai
2.5-star property

Aston at Poipu Kai

8/10 Very Good! (360 reviews)

Jan 5 - Jan 9

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 $1,372, price is now $1,019 per person
$1,019
per person
found 18 hours ago
Perfect little place close to the beach. Well equipped and very clean and well kept.

Reviewed on Jul 22, 2019

1 Hotel Hanalei Bay
5.0-star property

1 Hotel Hanalei Bay

9.2/10 Wonderful! (253 reviews)

Jan 5 - Jan 9

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 $3,813, price is now $2,579 per person
$2,579
per person
found 18 hours ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

Kiahuna Plantation Resort Kauai by OUTRIGGER
3.0-star property

Kiahuna Plantation Resort Kauai by OUTRIGGER

8.4/10 Very Good! (968 reviews)

Jan 5 - Jan 9

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 $1,811, price is now $1,362 per person
$1,362
per person
found 18 hours ago
The grounds are well maintained, however, the interior of the Condo was in serious need of upgrades and repairs. We have been staying here for years and as of recent they have cut cleaning services to once a week and towel replacement to once every 4 days. It seems that none of the mony received is reinvested into the condos themselves, we will be looking for other accommodations on our next vist.

Reviewed on Jul 23, 2025

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North Shore Kauai packages with premium economy flights

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 28 - Jan 2

5 night stay

Chicago (CHI) to Lihue (LIH)

United • PremiumEconomy

Lihue (LIH) to Chicago (CHI)

Delta • PremiumEconomy
Price was $6,142, price is now $4,547 per person
$4,547
per person
just found
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 28 - Jan 2

5 night stay

Chicago (CHI) to Lihue (LIH)

United • PremiumEconomy

Lihue (LIH) to Chicago (CHI)

Delta • PremiumEconomy
Save 100% on your flight
Price was $14,873, price is now $10,576 per person
$10,576
per person
just found
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 28 - Jan 2

5 night stay

Chicago (CHI) to Lihue (LIH)

United • PremiumEconomy

Lihue (LIH) to Chicago (CHI)

Delta • PremiumEconomy
Save 100% on your flight
Price was $11,938, price is now $9,213 per person
$9,213
per person
just found
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North Shore Kauai 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 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

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 18 hours 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 18 hours ago
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More About Flying To North Shore Kauai from Chicago

Route Information for Flights from Chicago to North Shore Kauai

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

Chicago to North Shore Kauai

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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.