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Find cheap flights from Chicago to Kailua from $211

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 Kailua departing on 8/20. 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 6/27
Thu 7/4

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Good to know

Low season

April

High season

July

Cheapest flight

$211
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Chicago O'Hare Airport to Honolulu

When to book flights from Chicago to Kailua

Are your dates flexible? Find out the best times to travel from Chicago to Kailua based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Kailua

  • Which airports will I be using when flying from Chicago to Kailua?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Kailua does not have its own airport so you’ll be flying into nearby Honolulu airport, which is 13.0 mi away.

  • How long does a flight from Chicago to Kailua take?

    Direct flights cover the 4,249 miles separating Chicago and Kailua in about 10h 54m.

  • How many flights are there between Chicago and Kailua?

    2 direct flights run between Chicago and Kailua on a daily basis. On average, there are about 14 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Kailua?

    Consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Kailua?

    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 Kailua.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kailua 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 Kailua?

    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 Kailua 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 Kailua?

    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 Kailua from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Kailua?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Kailua found on KAYAK was with American Airlines for $211. Alaska Airlines offered a round-trip connection from $421 and American Airlines from $422.

See more FAQs

Top tips for finding cheap flights from Chicago to Kailua

  • There is no airport in Kailua. Instead, you’ll be flying into Honolulu Airport when flying between Chicago and Kailua.
  • The cheapest flight from Chicago to Kailua was found 62 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is January.
See more tips

Top 4 airlines serving Chicago to Kailua

 
Need help choosing which airline to fly with from Chicago to Kailua? 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 9192 reviews
7.9Comfort
7.3Food
8.2Boarding
8.6Crew
7.3Entertainment
Airline reviews

Flights were on time. Check in was fine. Crew members were pleasant.

10.0 ExcellentAnonymous, May 2024TUS - SEA
Read more about Alaska Airlines reviews

Flights were on time. Check in was fine. Crew members were pleasant.

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

Great first time experience for me. The gate agent at the Anchorage location was so helpful. Definitely will be booking more on Alaska.

Delayed an hour and sat without updates. Ended up an hour late to destination

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.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

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.

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 Kailua

Recent round-trip flight deals

11/1Fri
1 stopAlaska Airlines
28h 54mORD-HNL
11/12Tue
1 stopAlaska Airlines
22h 46mHNL-ORD
$421
9/11Wed
1 stopAmerican Airlines
11h 23mORD-HNL
9/17Tue
1 stopAmerican Airlines
12h 05mHNL-ORD
$422
8/30Fri
1 stopDelta
11h 28mMDW-HNL
9/3Tue
1 stopDelta
13h 23mHNL-MDW
$422
9/4Wed
2 stopsDelta
18h 53mORD-HNL
9/10Tue
1 stopDelta
10h 33mHNL-ORD
$423
9/11Wed
2 stopsAmerican Airlines
13h 54mORD-HNL
9/25Wed
1 stopAmerican Airlines
11h 23mHNL-ORD
$427
9/4Wed
2 stopsDelta
18h 53mORD-HNL
9/10Tue
2 stopsDelta
15h 12mHNL-ORD
$428
8/26Mon
2 stopsDelta
18h 00mORD-HNL
9/6Fri
2 stopsDelta
15h 01mHNL-ORD
$432
9/7Sat
2 stopsDelta
16h 34mMDW-HNL
9/22Sun
2 stopsDelta
14h 33mHNL-MDW
$432
9/1Sun
1 stopDelta
13h 51mORD-HNL
10/2Wed
1 stopDelta
14h 58mHNL-ORD
$452
11/1Fri
1 stopAlaska Airlines
28h 54mORD-HNL
11/12Tue
2 stopsAlaska Airlines
28h 44mHNL-ORD
$455

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Recent one-way flight deals

8/20Tue
1 stopAmerican Airlines
12h 15mORD-HNL
$211
8/31Sat
2 stopsDelta
13h 26mORD-HNL
$216
8/31Sat
1 stopAlaska Airlines
29h 38mORD-HNL
$217
6/4Tue
3 stops
32h 56mORD-HNL
$253
6/3Mon
1 stopAlaska Airlines
20h 17mORD-HNL
$260
6/3Mon
2 stops
23h 57mORD-HNL
$285
8/24Sat
3 stopsWestJet
33h 03mORD-HNL
$297
7/24Wed
2 stopsUnited Airlines
18h 47mORD-HNL
$372
7/16Tue
2 stopsUnited Airlines
21h 20mORD-HNL
$393
7/25Thu
2 stopsWestJet
33h 03mORD-HNL
$448

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Last minute flights from Chicago to Kailua

Last minute flight, train and bus deals

5/31Fri
multi-stopAmerican Airlines
13h 54mORD-HNL
6/3Mon
multi-stopAmerican Airlines
11h 28mHNL-ORD
$566
5/31Fri
multi-stopDelta
12h 02mORD-HNL
6/6Thu
multi-stopDelta
15h 35mHNL-ORD
$575
5/31Fri
multi-stopAlaska Airlines
22h 59mORD-HNL
6/9Sun
multi-stopAlaska Airlines
28h 33mHNL-ORD
$580
5/31Fri
multi-stopDelta
12h 02mORD-HNL
6/2Sun
multi-stopDelta
11h 44mHNL-ORD
$588
5/31Fri
multi-stopDelta
12h 02mORD-HNL
6/5Wed
multi-stopDelta
11h 35mHNL-ORD
$597
5/31Fri
multi-stopDelta
12h 02mORD-HNL
6/10Mon
multi-stopDelta
20h 23mHNL-ORD
$603
5/29Wed
multi-stopDelta
14h 26mMDW-HNL
6/5Wed
multi-stopDelta
13h 01mHNL-MDW
$607
5/31Fri
multi-stopAlaska Airlines
22h 59mORD-HNL
6/11Tue
multi-stopAlaska Airlines
16h 14mHNL-ORD
$609
5/29Wed
multi-stopUnited Airlines
12h 25mORD-HNL
6/5Wed
nonstopUnited Airlines
8h 03mHNL-ORD
$1,164
5/31Fri
multi-stopUnited Airlines
24h 53mORD-HNL
6/8Sat
multi-stopUnited Airlines
21h 26mHNL-ORD
$1,207

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