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Find cheap flights from Chicago to Kaua'i from $251

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kaua'i departing on 7/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 6/6
Thu 6/13

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Best Kaua'i Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Lihue
Lihue2 stops$427

Good to know

Low season

October

High season

December

Cheapest flight

$251
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago O'Hare Airport to Lihue

FAQs - booking Kaua'i flights

  • How does KAYAK find such low prices on flights from Chicago to Kaua'i?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kaua'i.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Kaua'i?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kaua'i from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Kaua'i?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kaua'i with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Kaua'i?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kaua'i from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Chicago to Kaua'i

 
Need help choosing which airline to fly with from Chicago to Kaua'i? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9147 reviews
7.9Comfort
8.2Boarding
7.3Entertainment
7.3Food
8.6Crew
Airline reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

6.0 GoodAnonymous, May 2024SEA - HNL
Read more about Alaska Airlines reviews

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

I’m a first time mom and traveled with my 18mo old boy and it was not a great experience with the flight attendants. They were not friendly or helpful at all. It’s hard enough traveling with a toddler and have people be rude and unkind does not help.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

Window seat and a packed plane. A very uncomfortable flight.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Kaua'i

Recent round-trip flight deals

8/14Wed
2 stopsDelta
16h 22mORD-LIH
8/22Thu
1 stopDelta
11h 35mLIH-ORD
$427
10/29Tue
1 stopAmerican Airlines
12h 56mORD-LIH
11/5Tue
1 stopAmerican Airlines
13h 35mLIH-ORD
$434
9/2Mon
1 stopAmerican Airlines
11h 06mORD-LIH
9/9Mon
1 stopAmerican Airlines
11h 40mLIH-ORD
$441
9/2Mon
1 stopAmerican Airlines
11h 06mORD-LIH
9/9Mon
2 stopsAmerican Airlines
13h 02mLIH-ORD
$446
10/29Tue
1 stopAlaska Airlines
31h 59mORD-LIH
11/6Wed
1 stopAlaska Airlines
26h 07mLIH-ORD
$447
10/30Wed
1 stopAlaska Airlines
19h 33mORD-LIH
11/4Mon
1 stopAlaska Airlines
21h 06mLIH-ORD
$448
10/28Mon
1 stopDelta
16h 54mORD-LIH
11/6Wed
2 stopsDelta
15h 37mLIH-ORD
$451
9/2Mon
2 stopsDelta
15h 15mORD-LIH
9/9Mon
2 stopsDelta
15h 37mLIH-ORD
$456
9/12Thu
1 stopUnited Airlines
27h 53mORD-LIH
9/18Wed
1 stopUnited Airlines
11h 38mLIH-ORD
$642
9/11Wed
1 stopUnited Airlines
11h 57mORD-LIH
9/17Tue
1 stopUnited Airlines
11h 09mLIH-ORD
$685

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Recent one-way flight deals

7/10Wed
1 stopDelta
16h 33mORD-LIH
$251
7/8Mon
1 stopDelta
16h 33mORD-LIH
$271
6/12Wed
1 stopDelta
29h 15mORD-LIH
$290
6/11Tue
1 stopDelta
17h 10mORD-LIH
$313
5/17Fri
1 stopAmerican Airlines
11h 07mORD-LIH
$331
6/9Sun
1 stopAlaska Airlines
20h 04mORD-LIH
$350
6/15Sat
1 stopAlaska Airlines
30h 42mORD-LIH
$353
5/18Sat
1 stopAmerican Airlines
12h 54mORD-LIH
$388
6/28Fri
2 stopsUnited Airlines
19h 36mORD-LIH
$457
6/28Fri
1 stopUnited Airlines
17h 42mORD-LIH
$483

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Last minute flights from Chicago to Kaua'i

Last minute flight, train and bus deals

5/10Fri
multi-stopAmerican Airlines
12h 42mORD-LIH
5/21Tue
multi-stopAmerican Airlines
11h 20mLIH-ORD
$472
5/10Fri
multi-stopAmerican Airlines
16h 34mORD-LIH
5/21Tue
multi-stopAmerican Airlines
12h 18mLIH-ORD
$477
5/9Thu
multi-stopAlaska Airlines
20h 34mORD-LIH
5/12Sun
multi-stopAlaska Airlines
28h 09mLIH-ORD
$521
5/9Thu
multi-stopAmerican Airlines
11h 07mORD-LIH
5/12Sun
multi-stopAmerican Airlines
13h 00mLIH-ORD
$522
5/9Thu
multi-stopAmerican Airlines
15h 29mORD-LIH
5/12Sun
multi-stopAmerican Airlines
10h 36mLIH-ORD
$525
5/9Thu
multi-stopAmerican Airlines
12h 54mORD-LIH
5/23Thu
multi-stopAmerican Airlines
13h 00mLIH-ORD
$563
5/10Fri
multi-stopDelta
14h 22mORD-LIH
5/21Tue
multi-stopDelta
15h 39mLIH-ORD
$632
5/9Thu
multi-stopUnited Airlines
13h 31mORD-LIH
5/12Sun
multi-stopUnited Airlines
17h 22mLIH-ORD
$692
5/9Thu
multi-stop
24h 36mORD-LIH
5/23Thu
multi-stop
17h 15mLIH-ORD
$967
5/9Thu
multi-stopDelta
14h 28mMDW-LIH
5/12Sun
multi-stopDelta
16h 37mLIH-MDW
$2,018

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Flights to Kaua'i

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Kaua'i - Chicago

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