$172 Cheap flight deals from Chicago (CHI) to Kapaa (LIH)
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This Weekend's Flight Deals from Chicago to Kapaa
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.
ORD
O'Hare Intl.
LIH
Lihue
$468 Roundtrip, found 3 days ago
$468
Roundtrip
found 3 days ago
Airfares from $172 One Way, $340 Round Trip from Chicago to Kapaa
Prices starting at $340 for return flights and $172 for one-way flights to Kapaa were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
LIH
Kauai
$340 Roundtrip, found 6 days ago
$340
Roundtrip
found 6 days ago
ORD
Chicago
LIH
Kauai
$391 Roundtrip, found 1 day ago
$391
Roundtrip
found 1 day ago
ORD
Chicago
LIH
Kauai
$396 Roundtrip, found 1 day ago
$396
Roundtrip
found 1 day ago
ORD
Chicago
LIH
Kauai
$413 Roundtrip, found 1 day ago
$413
Roundtrip
found 1 day ago
ORD
Chicago
LIH
Kauai
$423 Roundtrip, found 1 day ago
$423
Roundtrip
found 1 day ago
Kapaa economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
OUTRIGGER Kauaʻi Beach Resort & Spa
8.4/10 Very Good! (1,427 reviews)
Feb 18 - Feb 24
6 night stay
Chicago (CHI) to Lihue (LIH)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,067, price is now $1,261 per person
$1,261
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
5.0-star property
1 Hotel Hanalei Bay
9.2/10 Wonderful! (275 reviews)
Mar 1 - Mar 7
6 night stay
Chicago (CHI) to Lihue (LIH)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,586, price is now $3,310 per person
$3,310
per person
found 1 day ago
Views were gorgeous and property is well maintained. The staff was extremely nice.
Reviewed on Jun 29, 2025
3.0-star property
Kiahuna Plantation Resort Kauai by OUTRIGGER
8.4/10 Very Good! (973 reviews)
Feb 21 - Feb 28
7 night stay
Chicago (CHI) to Lihue (LIH)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,075, price is now $1,978 per person
$1,978
per person
found 1 day 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
Kapaa packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
OUTRIGGER Kauaʻi Beach Resort & Spa
8.4/10 Very Good! (1,427 reviews)
Mar 2 - Mar 6
4 night stay
Chicago (ORD) to Lihue (LIH)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,913, price is now $1,445 per person
$1,445
per person
found 19 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
3.0-star property
Kauai Inn
9/10 Wonderful! (1,163 reviews)
Mar 2 - Mar 6
4 night stay
Chicago (ORD) to Lihue (LIH)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,904, price is now $1,496 per person
$1,496
per person
found 19 hours 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
4.0-star property
The Royal Sonesta Kaua'i Resort Lihue
9.2/10 Wonderful! (1,014 reviews)
Mar 2 - Mar 6
4 night stay
Chicago (ORD) to Lihue (LIH)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $2,127, price is now $1,772 per person
$1,772
per person
found 19 hours ago
My favorite beach/spot to be on the entire island. The beach is peaceful and beautiful to soak in. Plenty of loungers for guests. Walkable dining options. we went to all four parts of the island directionally- they’re basically same options so it’s nice to be in walking distance.
Do keep in mind the all the hidden fees, well it’s not really hidden but just account for parking/valet fee and daily resort fee. Everything Adds up. (Especially if you just charge everything to your room, easy to get carried away sometimes heheheh)
10/10 most peaceful trip I have ever taken. Along with my favorite part of our entire trip we went to Oahu, Maui, and Kauai.
Reviewed on Oct 8, 2025
Kapaa first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
OUTRIGGER Kauaʻi Beach Resort & Spa
8.4/10 Very Good! (1,427 reviews)
Feb 20 - Feb 27
7 night stay
Chicago (CHI) to Lihue (LIH)
United • FirstClass
Lihue (LIH) to Chicago (CHI)
American Airlines • FirstClass
Price was $4,429, price is now $3,604 per person
$3,604
per person
found 7 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
4.5-star property
Grand Hyatt Kauai Resort and Spa
9.4/10 Exceptional! (1,005 reviews)
Feb 20 - Feb 27
7 night stay
Chicago (CHI) to Lihue (LIH)
United • FirstClass
Lihue (LIH) to Chicago (CHI)
American Airlines • FirstClass
Price was $5,893, price is now $4,819 per person
$4,819
per person
found 7 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
4.0-star property
Waipouli Beach Resorts & Spa Kauai by OUTRIGGER
8.8/10 Excellent! (1,002 reviews)
Feb 20 - Feb 27
7 night stay
Chicago (CHI) to Lihue (LIH)
United • FirstClass
Lihue (LIH) to Chicago (CHI)
American Airlines • FirstClass
Price was $4,639, price is now $3,831 per person
$3,831
per person
found 7 hours 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
More About Flying To Kapaa from Chicago
Route Information for Flights from Chicago to Kapaa
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | LIH |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Kapaa
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Kapaa Airports
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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.
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