$205 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 9/18. 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
1 adult, Economy

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

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

Thu, Nov 6 - Sun, Nov 9
Southwest Logo
8:00 am - 1:30 amHNL-MDW
13h 30m1 stop
Southwest Logo
7:45 am - 4:15 pmMDW-HNL
12h 30m1 stop
$409Southwest
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Thu, Nov 6 - Sun, Nov 9
Southwest Logo
9:25 pm - 4:20 pmHNL-MDW
14h 55m2 stops
Southwest Logo
7:45 am - 4:15 pmMDW-HNL
12h 30m1 stop
$414Southwest
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Fri, Oct 24 - Sun, Oct 26
Alaska Airlines Logo
10:20 pm - 11:59 pmHNL-ORD
20h 39m1 stop
Alaska Airlines Logo
9:20 am - 4:55 pmORD-HNL
12h 35m1 stop
$421Alaska Airlines
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Thu, Sep 4 - Sun, Sep 7
Delta Logo
3:00 pm - 8:04 amHNL-ORD
12h 04m1 stop
Delta Logo
7:15 am - 2:19 pmORD-HNL
12h 04m1 stop
$423Delta
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Wed, Sep 10 - Sat, Sep 20
Delta Logo
10:42 pm - 5:15 pmHNL-ORD
13h 33m1 stop
Delta Logo
6:15 am - 6:57 pmORD-HNL
17h 42m2 stops
$428Delta
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Sat, Sep 13 - Sat, Sep 20
Hawaiian Airlines Logo
7:50 am - 12:04 amHNL-ORD
11h 14m1 stop
Hawaiian Airlines Logo
2:07 pm - 8:50 pmORD-HNL
11h 43m1 stop
$441Hawaiian Airlines
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Thu, Nov 6 - Sun, Nov 9
Alaska Airlines Logo
9:02 am - 6:59 pmHNL-ORD
29h 57m2 stops
Alaska Airlines Logo
9:20 am - 5:55 pmORD-HNL
12h 35m1 stop
$443Alaska Airlines
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Tue, Sep 9 - Wed, Sep 17
American Airlines Logo
11:02 pm - 3:51 pmHNL-ORD
11h 49m1 stop
American Airlines Logo
6:55 am - 7:33 pmORD-HNL
17h 38m1 stop
$481American Airlines
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Wed, Oct 1 - Tue, Oct 7
Hawaiian Airlines Logo
8:00 am - 12:03 amHNL-ORD
11h 03m1 stop
Hawaiian Airlines Logo
3:15 pm - 11:59 pmORD-HNL
13h 44m1 stop
$522Hawaiian Airlines
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Tue, Dec 23 - Mon, Jan 12
American Airlines Logo
7:00 pm - 7:10 amHNL-ORD
8h 10mnonstop
American Airlines Logo
2:14 pm - 10:44 pmORD-HNL
12h 30m1 stop
$561American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$205
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Honolulu to Chicago Midway 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.

Reviews of the 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 10000 reviews
8.1Boarding
7.1Food
7.1Entertainment
7.8Comfort
8.5Crew
Airline reviews

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

2.0 MediocreAnonymous, Jul 2025HNL - KOA
Read more Alaska Airlines reviews

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

I needed more space to sleep on an overnight flight.

Very good; ohana atmosphere and taking care of customer care

Flight was delayed an hour, so that was inconvenient. But they tried to make it up in the air, which I appreciated. Crew was very nice, service was excellent. Description of food didn’t quite match what was served, but it was tasty. 👍🏽

Really bad experience. Bad customer service from the check in process through the entire flight.

Wonderful staff who honored sleepy overnight travelers and still met needs quietly and quickly!

Wonderful respectful staff for a short flight late at night...lots of considerations all met!

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

1. On time flights. All of our, three separate, flights for three families were late 2. No food on the 5 1/2 hour flight. A substantial snack would have been good. 3. Seat upgrades are expensive 4. No place to move around or stretch on the 5 1/2 hour flight

It was fine. 2 hour delay due to mechanical issue. I understand issues will occur, just wish instead of Capt repeatedly telling us we will be getting off the ground “momentarily” they would just be honest and either say they have no idea-or it’s going to be a few hours! All in all FAs are usually pretty nice :)

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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.

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

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.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to O'ahu

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