$216 Find Cheap Flights from Chicago to Kailua

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 5/29. 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.
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Cheap Flight Deals from Chicago to Kailua (CHI-HNL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kailua that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Kailua

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Kailua.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
1:33 pm - 9:11 pmORD-HNL
12h 38m1 stop
American Airlines Logo
8:27 pm - 2:15 pmHNL-ORD
12h 48m1 stop
$461American Airlines
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Fri, May 30 - Thu, Jun 5
Alaska Airlines Logo
7:18 pm - 10:15 pmORD-HNL
31h 57m1 stop
Alaska Airlines Logo
1:10 pm - 7:03 amHNL-ORD
12h 53m1 stop
$465Alaska Airlines
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Sat, Aug 16 - Tue, Aug 26
American Airlines Logo
8:50 am - 4:51 pmORD-HNL
13h 01m1 stop
American Airlines Logo
10:43 pm - 2:17 pmHNL-ORD
10h 34m1 stop
$467American Airlines
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Sun, Sep 14 - Tue, Sep 23
Delta Logo
7:30 am - 7:20 pmORD-HNL
16h 50m1 stop
Delta Logo
12:35 pm - 7:26 amHNL-ORD
13h 51m2 stops
$473Delta
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Sun, Sep 14 - Tue, Sep 23
Delta Logo
9:30 am - 9:20 pmORD-HNL
16h 50m2 stops
Delta Logo
8:25 pm - 4:47 pmHNL-ORD
15h 22m2 stops
$478Delta
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Wed, Sep 3 - Thu, Sep 11
Delta Logo
9:20 am - 9:20 pmMDW-HNL
17h 00m2 stops
Delta Logo
12:35 pm - 8:46 amHNL-MDW
15h 11m2 stops
$478Delta
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Wed, Sep 3 - Thu, Sep 11
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
8:05 am - 12:30 amHNL-MDW
11h 25m1 stop
$479Southwest
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Wed, Sep 3 - Thu, Sep 11
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
Southwest Logo
11:35 am - 10:30 amHNL-MDW
17h 55m2 stops
$497Southwest
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Wed, Sep 3 - Thu, Sep 11
Alaska Airlines Logo
7:00 am - 8:37 pmORD-HNL
18h 37m1 stop
Alaska Airlines Logo
1:40 pm - 6:59 pmHNL-ORD
24h 19m1 stop
$510Alaska Airlines
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Tue, May 27 - Mon, Jun 2
United Airlines Logo
7:43 pm - 11:18 amORD-HNL
20h 35m2 stops
United Airlines Logo
7:00 am - 5:10 amHNL-ORD
17h 10m1 stop
$669United Airlines
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Fri, Oct 17 - Tue, Oct 28
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Good to know

Low seasonApril
High seasonMarch
Cheapest flight$216
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 16% 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 37m.

  • 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 Tuesdays 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 Wednesdays.

  • 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 Delta for $216. American Airlines offered a round-trip connection from $461 and Alaska Airlines from $465.

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 53 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 November, December and January. The cheapest month to fly is February.

Top 5 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 9968 reviews
7.9Comfort
8.2Boarding
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

6.0 GoodJulie, Apr 2025LAX - LIH
Read more Alaska Airlines reviews

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

Tight legroom. The breakfast was provided, which was a plus, and okay the taste.

Awful. We got the last seats and they don't recline. We've been on this horrible journey since 6am and won't get to our destination almost a full day later. Oh and no food, either. Never again.

Self check in is not indicated well if you approach Terminal 1 from Terminal 2 Parking

Ted. F/A in fist class did a great job! Very nice

While the flight itself was pleasant, the process of checking in was difficult. The line was long and our connection time was but two hours. When we finally got to the Hawaiian agent and told him that we were traveling on Alaskan Airlines, he told us we would need to go to a different terminal. I told him that another Hawaiian Airlines agent had directed us to him. I’m looking at our tickets, he noticed that the Alaskan Airlines flight was to be managed by a second party. He ended admonish us for not telling us so Rather than considering that we might’ve been right in the first place.

Only problem my credit card had over three pending credit card charges for luggages. I hope these charges do not post. I have already contacted my credit card companies.

Plane left an hour late due to flight staffing problems. Only a 45 min flight, but it took 3 hours as a result, which left a lot of people disgruntled. No excuses. No recompense.

Paid for first class, but the flight attendant for first class did the minimum required. She really ever came to pick up the trash, and never asked if we needed anything. Every person had to ring for the flight attendants if they wanted any extra drinks. When I went back to use the restroom, she was just sitting on her phone.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Everything you need to know for your flight from Chicago to Kailua

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