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Find cheap flights from Chicago to O'ahu from $258

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 O'ahu departing on 5/16. 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
Fri 5/24
Fri 5/31

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Best O'ahu Flight Deals

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

Honolulu
Honolulu1 stop$527

Good to know

Low season

October

High season

March

Cheapest flight

$258
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago O'Hare Airport to Honolulu

FAQs - booking O'ahu flights

  • How does KAYAK find such low prices on flights from Chicago to O'ahu?

    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 O'ahu.

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

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

    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 O'ahu 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 O'ahu?

    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 O'ahu 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 O'ahu

 
Need help choosing which airline to fly with from Chicago to O'ahu? 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.
8.1
Alaska AirlinesOverall score based on 9111 reviews
7.3food
8.2boarding
8.6crew
7.9comfort
7.3entertainment
Airline reviews

Flight was good. Glad it was delayed or I may have missed the connection since I got to Seattle at about the same time my connection was to leave. The snack was a small bag of pretzels and a small soda. Can’t really call that food. There was no entertainment available on the flight.

8.0 ExcellentAnonymous, Apr 2024SEA - TUS
Read more about Alaska Airlines reviews

Flight was good. Glad it was delayed or I may have missed the connection since I got to Seattle at about the same time my connection was to leave. The snack was a small bag of pretzels and a small soda. Can’t really call that food. There was no entertainment available on the flight.

It was much better than expected. Short flight and smaller plane so no entertainment or food.

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.

My flights went about as good as they could be. I’ll always take Alaska when possible.

The pilot and crew did everything they possibly could on an airline flight to make everyone comfortable and fed and informed and both flights to and from were flawless and safe and I couldn't imagine flying on another airline when I visit the Hawaiian islands

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

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.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

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 O'ahu

Recent round-trip flight deals

5/12Sun
1 stopAlaska Airlines
22h 58mORD-HNL
5/21Tue
1 stopAlaska Airlines
11h 54mHNL-ORD
$527
5/27Mon
1 stopAlaska Airlines
25h 24mORD-HNL
6/2Sun
1 stopAlaska Airlines
14h 01mHNL-ORD
$528
5/15Wed
1 stopAmerican Airlines
10h 45mORD-HNL
5/21Tue
1 stopAmerican Airlines
12h 35mHNL-ORD
$532
5/11Sat
1 stopAmerican Airlines
11h 21mORD-HNL
5/14Tue
1 stopAmerican Airlines
11h 28mHNL-ORD
$563
5/30Thu
1 stop
11h 18mORD-HNL
6/12Wed
1 stop
11h 27mHNL-ORD
$566
5/6Mon
2 stops
20h 48mORD-HNL
5/12Sun
2 stops
20h 29mHNL-ORD
$611
4/27Sat
1 stopDelta
13h 31mORD-HNL
5/4Sat
2 stopsDelta
14h 52mHNL-ORD
$615
4/27Sat
2 stopsDelta
14h 24mORD-HNL
5/4Sat
2 stopsDelta
14h 52mHNL-ORD
$620
5/21Tue
1 stopUnited Airlines
15h 22mORD-HNL
5/28Tue
1 stopUnited Airlines
11h 15mHNL-ORD
$701
5/14Tue
2 stopsUnited Airlines
17h 33mORD-HNL
5/21Tue
2 stopsUnited Airlines
16h 47mHNL-ORD
$711

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Recent one-way flight deals

5/16Thu
1 stopAmerican Airlines
12h 31mORD-HNL
$258
5/14Tue
1 stopAmerican Airlines
10h 45mORD-HNL
$266
5/3Fri
1 stopDelta
12h 35mORD-HNL
$305
5/3Fri
2 stopsDelta
15h 24mORD-HNL
$310
5/1Wed
1 stopAlaska Airlines
25h 29mORD-HNL
$317
5/30Thu
1 stopAlaska Airlines
30h 48mORD-HNL
$329
5/14Tue
2 stopsUnited Airlines
16h 38mORD-HNL
$335
5/2Thu
1 stopUnited Airlines
14h 58mORD-HNL
$352
6/10Mon
3 stops
30h 39mORD-HNL
$415
5/8Wed
3 stops
41h 19mMDW-HNL
$519

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Last minute flights from Chicago to O'ahu

Last minute flight, train and bus deals

4/27Sat
multi-stopAlaska Airlines
13h 11mORD-HNL
5/5Sun
multi-stopAlaska Airlines
28h 15mHNL-ORD
$609
4/28Sun
multi-stopAmerican Airlines
13h 46mORD-HNL
5/5Sun
multi-stopAmerican Airlines
10h 34mHNL-ORD
$610
4/27Sat
multi-stopDelta
13h 31mORD-HNL
5/4Sat
multi-stopDelta
14h 52mHNL-ORD
$615
4/27Sat
multi-stopDelta
14h 24mORD-HNL
5/4Sat
multi-stopDelta
14h 52mHNL-ORD
$620
4/27Sat
multi-stopAlaska Airlines
32h 31mORD-HNL
5/7Tue
multi-stopAlaska Airlines
24h 10mHNL-ORD
$646
4/27Sat
multi-stopDelta
14h 24mORD-HNL
5/7Tue
multi-stopDelta
11h 44mHNL-ORD
$652
4/26Fri
multi-stopAlaska Airlines
18h 07mORD-HNL
5/2Thu
multi-stopAlaska Airlines
11h 24mHNL-ORD
$656
4/28Sun
multi-stopAmerican Airlines
13h 46mORD-HNL
4/29Mon
multi-stopAmerican Airlines
11h 34mHNL-ORD
$736
4/27Sat
multi-stopUnited Airlines
14h 51mORD-HNL
5/1Wed
nonstopUnited Airlines
8h 11mHNL-ORD
$1,113
4/27Sat
multi-stopUnited Airlines
13h 48mORD-HNL
5/5Sun
multi-stopUnited Airlines
12h 12mHNL-ORD
$1,160

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Flights to O'ahu

Return flight deals:

O'ahu - Chicago

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$311
$328
$277
$32

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