$201 Cheap flight deals from Chicago (CHI) to Princeville (LIH)

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This Weekend's Flight Deals from Chicago to Princeville

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 - Wed, Jan 7
ORD
O'Hare Intl.
LIH
Lihue
$673 Roundtrip, found 16 hours ago
$673
Roundtrip
found 16 hours ago
Select Delta flight, departing Fri, Jan 2 from O'Hare Intl. to Lihue, returning Wed, Jan 7, priced at $673 found 16 hours ago

Airfares from $201 One Way, $389 Round Trip from Chicago to Princeville

Prices starting at $389 for return flights and $201 for one-way flights to Princeville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jan 29 - Thu, Feb 5
ORD
Chicago
LIH
Kauai
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Thu, Jan 29 from Chicago to Kauai, returning Thu, Feb 5, priced at $389 found 5 days ago
Tue, Jan 27 - Tue, Feb 3
ORD
Chicago
LIH
Kauai
$395 Roundtrip, found 5 days ago
$395
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Jan 27 from Chicago to Kauai, returning Tue, Feb 3, priced at $395 found 5 days ago
Wed, Feb 4 - Tue, Feb 10
ORD
Chicago
LIH
Kauai
$399 Roundtrip, found 5 days ago
$399
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Feb 4 from Chicago to Kauai, returning Tue, Feb 10, priced at $399 found 5 days ago
Wed, Feb 18 - Thu, Feb 26
ORD
Chicago
LIH
Kauai
$403 Roundtrip, found 2 days ago
$403
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Feb 18 from Chicago to Kauai, returning Thu, Feb 26, priced at $403 found 2 days ago
Wed, Feb 4 - Tue, Feb 10
ORD
Chicago
LIH
Kauai
$404 Roundtrip, found 5 days ago
$404
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Feb 4 from Chicago to Kauai, returning Tue, Feb 10, priced at $404 found 5 days ago

Princeville 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)

Feb 18 - Feb 22

4 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • Non-stop roundtrip • Coach
Price was $1,608, price is now $1,115 per person
$1,115
per person
found 17 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

Kauai Inn
3.0-star property

Kauai Inn

9/10 Wonderful! (1,163 reviews)

Feb 5 - Feb 12

7 night stay

Chicago (ORD) to Lihue (LIH)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,858, price is now $1,226 per person
$1,226
per person
found 1 day ago
I’ve been at Kaua’i Inn and enjoyed it in the past. This was the first I was placed into an ADA room as it seemed to suit someone in a wheelchair. The room had less furniture. I wish I had a small table or counter to better do my computer work. When I re-book, I will be sure to request a normal room.

Reviewed on Sep 22, 2025

Grand Hyatt Kauai Resort and Spa
4.5-star property

Grand Hyatt Kauai Resort and Spa

9.4/10 Exceptional! (1,005 reviews)

Feb 13 - Feb 17

4 night stay

Chicago (ORD) to Lihue (LIH)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,098, price is now $3,421 per person
$3,421
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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Princeville 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! (1,001 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • FirstClass

Lihue (LIH) to Chicago (CHI)

United • FirstClass
Price was $5,560, price is now $4,298 per person
$4,298
per person
found 19 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! (275 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • FirstClass

Lihue (LIH) to Chicago (CHI)

United • FirstClass
Price was $8,441, price is now $6,222 per person
$6,222
per person
found 19 hours ago
Views were gorgeous and property is well maintained. The staff was extremely nice.

Reviewed on Jun 29, 2025

Grand Hyatt Kauai Resort and Spa
4.5-star property

Grand Hyatt Kauai Resort and Spa

9.4/10 Exceptional! (1,005 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Lihue (LIH)

Alaska Airlines • FirstClass

Lihue (LIH) to Chicago (CHI)

United • FirstClass
Price was $5,371, price is now $4,329 per person
$4,329
per person
found 19 hours 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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More About Flying To Princeville from Chicago

Route Information for Flights from Chicago to Princeville

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

Chicago to Princeville

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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.