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Find cheap flights from Chicago to Kailua from $209

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 8/13. 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
Mon 7/8
Mon 7/15

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Low season

April

High season

July

Cheapest flight

$209
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 50m.

  • 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 Monday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

  • 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 Alaska Airlines for $209. Alaska Airlines offered a round-trip connection from $376 and Delta from $423.

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 9236 reviews
8.2Boarding
7.9Comfort
7.3Entertainment
7.3Food
8.6Crew
Airline reviews

Mediocre is best way to describe. Bare bones narrow seats, Dirty pulldown tray, unfriendly cabin crew who were in a hurry to serve tiny drinks and tiny snacks. (Compared to much better Hawaiian Airlines experience, .. no comparison!)

4.0 OkayAndrew, Jun 2024HNL - SFO
Read more about Alaska Airlines reviews

Mediocre is best way to describe. Bare bones narrow seats, Dirty pulldown tray, unfriendly cabin crew who were in a hurry to serve tiny drinks and tiny snacks. (Compared to much better Hawaiian Airlines experience, .. no comparison!)

The people who worked for Alaska Airlines, both on the ground at O'Hare and during the flight, made it remarkable for me. Their customer service is incredible; they're kind of like the Nordstrom of the sky.

We loved the extra legroom on the flight and the fact that we didn’t have any one beside us.Everything was a n time and satisfactory.

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.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

Book cheap flights from Chicago to Kailua

Recent round-trip flight deals

9/23Mon
2 stopsAlaska Airlines
21h 02mORD-HNL
10/1Tue
1 stopAlaska Airlines
21h 24mHNL-ORD
$376
9/24Tue
1 stopAlaska Airlines
25h 45mORD-HNL
10/1Tue
1 stopAlaska Airlines
21h 24mHNL-ORD
$382
11/1Fri
1 stopAlaska Airlines
23h 18mORD-HNL
11/15Fri
1 stopAlaska Airlines
19h 58mHNL-ORD
$385
9/23Mon
2 stopsAlaska Airlines
21h 02mORD-HNL
10/1Tue
2 stopsAlaska Airlines
28h 36mHNL-ORD
$395
9/4Wed
2 stopsDelta
18h 53mORD-HNL
9/11Wed
1 stopDelta
10h 56mHNL-ORD
$423
10/31Thu
2 stopsDelta
17h 02mORD-HNL
11/7Thu
1 stopDelta
10h 46mHNL-ORD
$427
8/13Tue
1 stopAmerican Airlines
10h 50mORD-HNL
8/20Tue
1 stopAmerican Airlines
19h 35mHNL-ORD
$480
9/19Thu
2 stopsAmerican Airlines
13h 54mORD-HNL
9/22Sun
1 stopAmerican Airlines
12h 41mHNL-ORD
$547
12/4Wed
1 stopUnited Airlines
15h 48mORD-HNL
12/6Fri
1 stopUnited Airlines
17h 34mHNL-ORD
$575
12/4Wed
1 stopUnited Airlines
14h 25mORD-HNL
12/11Wed
2 stopsUnited Airlines
16h 54mHNL-ORD
$619

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Recent one-way flight deals

8/13Tue
1 stopAlaska Airlines
12h 34mORD-HNL
$209
9/1Sun
1 stopAlaska Airlines
18h 05mORD-HNL
$211
8/26Mon
1 stopDelta
11h 28mMDW-HNL
$211
9/1Sun
2 stopsDelta
14h 56mORD-HNL
$216
9/19Thu
2 stopsAmerican Airlines
16h 17mORD-HNL
$286
9/1Sun
2 stopsUnited Airlines
18h 10mORD-HNL
$294
9/1Sun
3 stops
32h 53mORD-HNL
$335
9/1Sun
3 stops
32h 53mORD-HNL
$337
7/26Fri
1 stopUnited Airlines
21h 20mORD-HNL
$383
6/15Sat
1 stopAmerican Airlines
11h 10mORD-HNL
$523

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Last minute flights from Chicago to Kailua

Last minute flight, train and bus deals

6/9Sun
multi-stopAmerican Airlines
12h 10mORD-HNL
6/13Thu
multi-stopAmerican Airlines
11h 42mHNL-ORD
$742
6/11Tue
multi-stopAlaska Airlines
32h 08mORD-HNL
6/16Sun
multi-stopAlaska Airlines
27h 30mHNL-ORD
$744
6/11Tue
multi-stopAlaska Airlines
32h 08mORD-HNL
6/18Tue
multi-stopAlaska Airlines
11h 39mHNL-ORD
$796
6/11Tue
multi-stopAmerican Airlines
13h 00mORD-HNL
6/16Sun
multi-stopAmerican Airlines
11h 42mHNL-ORD
$823
6/11Tue
multi-stopAlaska Airlines
32h 46mORD-HNL
6/18Tue
multi-stopAlaska Airlines
30h 39mHNL-ORD
$837
6/11Tue
multi-stopDelta
12h 25mORD-HNL
6/13Thu
multi-stopDelta
14h 59mHNL-ORD
$838
6/9Sun
multi-stopAmerican Airlines
11h 08mORD-HNL
6/11Tue
multi-stopAmerican Airlines
11h 41mHNL-ORD
$839
6/11Tue
multi-stopDelta
12h 25mORD-HNL
6/13Thu
multi-stopDelta
14h 20mHNL-ORD
$848
6/12Wed
multi-stopUnited Airlines
17h 12mORD-HNL
6/19Wed
multi-stopUnited Airlines
16h 33mHNL-ORD
$1,000
6/11Tue
multi-stopUnited Airlines
17h 12mORD-HNL
6/18Tue
multi-stopUnited Airlines
17h 07mHNL-ORD
$1,018

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