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Cheap Flights from O'ahu to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'ahu to Chicago

Tue, Oct 20 - Mon, Oct 26
Multiple Airlines Logo
8:35 pm - 4:50 pmHNL  Honolulu-ORD Chicago O'Hare Intl
15h 15m2 stops Los Angeles Los Angeles Seattle/Tacoma Intl
Multiple Airlines Logo
7:49 pm - 12:03 pmORD  Chicago O'Hare Intl-HNL Honolulu
21h 14m1 stop San Diego
$454Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
11:55 pm - 6:20 pmHNL  Honolulu-ORD Chicago O'Hare Intl
13h 25m1 stop Seattle/Tacoma Intl
Multiple Airlines Logo
7:20 am - 9:32 pmORD  Chicago O'Hare Intl-HNL Honolulu
18h 12m1 stop San Diego
$455Multiple Airlines
Tue, Feb 2 - Wed, Feb 3
Alaska Airlines Logo
8:10 am - 11:59 pmHNL  Honolulu-ORD Chicago O'Hare Intl
11h 49m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:11 pm - 10:08 pmORD  Chicago O'Hare Intl-HNL Honolulu
11h 57m1 stop Portland
$486Alaska Airlines
Thu, Nov 5 - Mon, Nov 9
Alaska Airlines Logo
11:09 pm - 6:59 pmHNL  Honolulu-ORD Chicago O'Hare Intl
15h 50m1 stop San Diego
Alaska Airlines Logo
7:20 am - 3:21 pmORD  Chicago O'Hare Intl-HNL Honolulu
12h 01m1 stop San Diego
$490Alaska Airlines
Thu, Nov 5 - Sat, Nov 14
Delta Logo
4:15 pm - 7:41 amHNL  Honolulu-ORD Chicago O'Hare Intl
11h 26m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 8:57 pmORD  Chicago O'Hare Intl-HNL Honolulu
15h 27m1 stop Los Angeles Los Angeles
$539Delta
Thu, Nov 5 - Sat, Nov 14
Delta Logo
11:40 pm - 4:53 pmHNL  Honolulu-ORD Chicago O'Hare Intl
13h 13m1 stop Seattle/Tacoma Intl
Delta Logo
5:30 am - 8:57 pmORD  Chicago O'Hare Intl-HNL Honolulu
19h 27m2 stops Atlanta Hartsfield-Jackson Los Angeles Los Angeles
$545Delta
Wed, Dec 23 - Tue, Jan 5
United Airlines Logo
7:45 pm - 7:56 amHNL  Honolulu-ORD Chicago O'Hare Intl
8h 11mnonstop
United Airlines Logo
12:45 pm - 9:11 pmORD  Chicago O'Hare Intl-HNL Honolulu
12h 26m1 stop Los Angeles Los Angeles
$556United Airlines
Wed, Dec 23 - Wed, Dec 30
United Airlines Logo
4:50 pm - 5:01 amHNL  Honolulu-ORD Chicago O'Hare Intl
8h 11mnonstop
United Airlines Logo
10:47 am - 6:26 pmORD  Chicago O'Hare Intl-HNL Honolulu
11h 39m1 stop Denver Intl
$556United Airlines
Tue, Oct 27 - Tue, Nov 3
American Airlines Logo
6:01 pm - 7:00 amHNL  Honolulu-ORD Chicago O'Hare Intl
7h 59mnonstop
American Airlines Logo
10:00 am - 3:18 pmORD  Chicago O'Hare Intl-HNL Honolulu
9h 18mnonstop
$565American Airlines
Thu, Dec 3 - Mon, Dec 7
American Airlines Logo
7:00 pm - 7:20 amHNL  Honolulu-ORD Chicago O'Hare Intl
8h 20mnonstop
American Airlines Logo
10:00 am - 3:25 pmORD  Chicago O'Hare Intl-HNL Honolulu
9h 25mnonstop
$567American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$221
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Honolulu to Chicago O'Hare Airport

FAQs for booking O'ahu to Chicago flights

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

    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 O'ahu to Chicago.

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

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

    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 Chicago with an airline and back to O'ahu with another airline.

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

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

Reviews of the top 4 airlines serving from O'ahu to Chicago

 
Need help choosing which airline to fly with from O'ahu to Chicago? 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.
7.9
Alaska AirlinesOverall score based on 12931 reviews
8.1Boarding
8.5Crew
7.0Food
7.8Comfort
7.0Entertainment
Airline reviews

Anything to make the customer experience better. Stop cancelling flights like people traveling have nothing better to do than have their life plans halted. People go to great lengths to get time off work, make plans at the end of their flights, make travel plans, go through the nightmare of checking in at busy stressful airports, make pick up arrangements only to have the rug pulled out from under them. Flying has become so miserable now!! The flights were delayed ONLY with American Airlines. The disorganization is sickening. After the flight being delayed multiple times, when the flight was finally broadcast that it was a go, EXCEPT, they were now waiting for flight attendants. They had plenty of time to plan this, what the heck?! Missed both connecting flights because it was so delayed. I vowed to never fly American Airlines again, did it and BOY was it a mistake!!! American Airlines ranks with United as two worst airlines.

2.0 MediocreAnonymous, Sep 2026
Read more Alaska Airlines reviews

Anything to make the customer experience better. Stop cancelling flights like people traveling have nothing better to do than have their life plans halted. People go to great lengths to get time off work, make plans at the end of their flights, make travel plans, go through the nightmare of checking in at busy stressful airports, make pick up arrangements only to have the rug pulled out from under them. Flying has become so miserable now!! The flights were delayed ONLY with American Airlines. The disorganization is sickening. After the flight being delayed multiple times, when the flight was finally broadcast that it was a go, EXCEPT, they were now waiting for flight attendants. They had plenty of time to plan this, what the heck?! Missed both connecting flights because it was so delayed. I vowed to never fly American Airlines again, did it and BOY was it a mistake!!! American Airlines ranks with United as two worst airlines.

Potatoes were not cooked in the pork potato meal. Flight attendants were great in first class.

I paid extra to choose my seat. I chose a window seat. I don’t know if it was a disconnect between KAYAK or the airline but when we got to the airport, the seat was changed to a middle seat. Didn’t notice it til at the gate. I called wanted a refund and was told that I didn’t choose the seat even though on my KAYAK reservation it showed seat 12 A. So I paid extra for seat selection, but didn’t get it. And also did not get a refund. I specifically pay the extra for a seat selection. I normally am very happy with Alaska Airlines. They are usually in my top three of choices.

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

Worst travel day of my life. First bumped from our 7am flight—that we booked to ensure enough time to get to Chicago and get ready to go to a concert. Ended up on a flight 5hours later only to arrive in Chicago and spend 2 hours sitting in the tarmac. Missed the concert ($650 in tickets) and was too late to cancel the hotel ($500). I did receive a $200 voucher for the next Alaska ticket—soooo generous 👎. Would LOVE if Alaska reimbursed the $1000+that I am out!

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was very warm the entire time, despite my vents being open. Additionally, we didn't have internet on our personal devices

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

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

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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