$216 Find Cheap Flights from O'ahu to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/5. 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 Flights from O'ahu to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'ahu to Chicago 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 O'ahu to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from O'ahu to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
3:21 pm - 7:49 amHNL-ORD
11h 28m1 stop
Delta Logo
7:15 am - 6:55 pmORD-HNL
16h 40m1 stop
$457Delta
Find Deal
Thu, May 22 - Thu, May 29
Delta Logo
1:20 pm - 8:24 amHNL-ORD
14h 04m2 stops
Delta Logo
7:15 am - 6:55 pmORD-HNL
16h 40m1 stop
$462Delta
Find Deal
Thu, May 22 - Thu, May 29
Southwest Logo
9:05 pm - 2:10 pmHNL-ORD
12h 05m2 stops
Southwest Logo
6:55 pm - 10:20 amORD-HNL
20h 25m2 stops
$502Southwest
Find Deal
Tue, Sep 9 - Mon, Sep 15
American Airlines Logo
10:43 pm - 2:17 pmHNL-ORD
10h 34m1 stop
American Airlines Logo
8:50 am - 4:51 pmORD-HNL
13h 01m1 stop
$525American Airlines
Find Deal
Thu, Sep 4 - Thu, Sep 11
American Airlines Logo
9:11 pm - 2:12 pmHNL-ORD
12h 01m1 stop
American Airlines Logo
10:05 am - 4:18 pmORD-HNL
11h 13m1 stop
$535American Airlines
Find Deal
Thu, Aug 21 - Tue, Aug 26
Southwest Logo
8:10 am - 11:25 pmHNL-MDW
10h 15m1 stop
Southwest Logo
9:10 pm - 10:20 amMDW-HNL
18h 10m1 stop
$563Southwest
Find Deal
Thu, Sep 4 - Thu, Sep 11
Alaska Airlines Logo
11:45 pm - 5:40 amHNL-ORD
24h 55m1 stop
Alaska Airlines Logo
3:17 pm - 11:07 pmORD-HNL
12h 50m1 stop
$568Alaska Airlines
Find Deal
Wed, May 28 - Thu, Jun 5
Alaska Airlines Logo
11:45 pm - 5:40 amHNL-ORD
24h 55m1 stop
Alaska Airlines Logo
7:51 pm - 11:07 pmORD-HNL
32h 16m1 stop
$570Alaska Airlines
Find Deal
Mon, May 19 - Tue, May 27
United Airlines Logo
7:00 am - 4:51 amHNL-ORD
16h 51m2 stops
United Airlines Logo
6:00 am - 4:01 pmORD-HNL
15h 01m1 stop
$795United Airlines
Find Deal
Mon, Jun 23 - Sat, Jun 28
United Airlines Logo
8:30 am - 12:40 pmHNL-ORD
23h 10m2 stops
United Airlines Logo
6:48 am - 4:29 pmORD-HNL
14h 41m1 stop
$851United Airlines
Find Deal
Tue, Jun 10 - Sun, Jun 15
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$216
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Honolulu to Chicago O'Hare Airport

FAQs for booking flights from O'ahu to Chicago

  • 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.

Top 5 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.
8.0
Alaska AirlinesOverall score based on 9972 reviews
8.1Boarding
7.9Comfort
7.1Food
7.1Entertainment
8.5Crew
Airline reviews

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.)

2.0 MediocreJános, Apr 2025KOA - OGG
Read more Alaska Airlines reviews

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.)

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

1.5 hour delay boarding plus 1+ hour sitting in plane waiting for ground crew to load luggage and freight, made for 3:00AM arrival in Seattle.

The plane was freezing and no blanquets available unless you buy them. My screen was bad so I couldn’t watch any entertainment.

Great service, great options, flight was bumpy so didn't get second beverage service and everything was communicated very clearly and courteously. No notes: everyone did great! Also loved the fun Hawaiian drink options (non-alcoholic).

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.

We had to cancel and we’re treated fairly with 100%refund quickly

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.

Probably the worst 1st Class I have ever experienced. Sam, our flight attendant, was excellent. Other than that, everything from the Alaska Longe experience to the buggy app to the uncomfortable flight and uncommunicative agents were poor. The agent who booked us in forgot to mark TSA PreCheck on our boarding passes and we had to go back to get this done. They were a cut below every other airline we have experienced in just about every area.

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

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.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

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.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Everything you need to know for your flight to Chicago

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