$200 Find Cheap Flights from O'ahu to Chicago - Compare and Save

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 10/27. 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, 0 bags

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Flight Deals

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, Jul 30 - Fri, Aug 7
Multiple Airlines Logo
7:00 am - 11:59 pm
HNL
-
ORD
11h 59m
1 stop
Multiple Airlines Logo
6:00 am - 8:53 pm
ORD
-
HNL
19h 53m
2 stops
$575Multiple Airlines
Tue, Oct 6 - Wed, Oct 21
Multiple Airlines Logo
7:30 am - 11:59 pm
HNL
-
ORD
11h 29m
1 stop
Multiple Airlines Logo
7:20 am - 6:32 pm
ORD
-
HNL
16h 12m
2 stops
$577Multiple Airlines
Mon, Jul 27 - Mon, Aug 10
Multiple Airlines Logo
3:07 pm - 12:03 pm
HNL
-
ORD
15h 56m
1 stop
Multiple Airlines Logo
6:20 am - 8:22 pm
ORD
-
HNL
19h 02m
1 stop
$580Multiple Airlines
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
Southwest Logo
12:20 pm - 9:15 pm
MDW
-
HNL
13h 55m
1 stop
$584Southwest
Fri, Dec 4 - Mon, Jan 4
Southwest Logo
10:05 pm - 5:35 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
11:10 am - 9:20 pm
MDW
-
HNL
14h 10m
2 stops
$588Southwest
Thu, Aug 20 - Tue, Aug 25
Southwest Logo
8:10 am - 11:45 pm
HNL
-
MDW
10h 35m
1 stop
Southwest Logo
11:00 am - 9:20 pm
MDW
-
HNL
15h 20m
2 stops
$590Southwest
Fri, Dec 4 - Mon, Jan 4
Southwest Logo
10:05 pm - 5:35 pm
HNL
-
MDW
15h 30m
1 stop
Southwest Logo
10:10 am - 9:10 pm
MDW
-
HNL
15h 00m
1 stop
$592Southwest
Thu, Aug 6 - Thu, Aug 13
Delta Logo
1:00 pm - 8:30 am
HNL
-
ORD
14h 30m
2 stops
Delta Logo
2:36 pm - 9:20 pm
ORD
-
HNL
11h 44m
1 stop
$598Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
4:18 pm - 12:39 pm
HNL
-
MDW
15h 21m
2 stops
Delta Logo
9:20 am - 8:47 pm
MDW
-
HNL
16h 27m
2 stops
$603Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
3:10 pm - 10:42 am
HNL
-
ORD
14h 32m
2 stops
Delta Logo
9:30 am - 8:47 pm
ORD
-
HNL
16h 17m
2 stops
$603Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$200
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 1% increase in price.
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.

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.
7.9
Alaska AirlinesOverall score based on 12522 reviews
7.8Comfort
7.1Food
8.1Boarding
8.5Crew
7.0Entertainment
Airline reviews

My flight was several times rescheduled and then finally canceled.

2.0 MediocrePeter, Jun 2026
SAN - ORD
Read more Alaska Airlines reviews

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!

Good flight overall. Lots of bumps during flight but pilot kept searching for smooth air

We tried for days to use online Alaska Airline app we needed to know what Gate to depart from . When we got there we were given a paper boarding ticket with the wrong gate on it . We almost missed this flight . It caused great stress and caused a health side effect. The previous flights April 24 started hour late mechanical issues . We were not allowed to depart plane in time to get correct gate and missed our flight .

Couldn’t order food for the family because all the good food was unavailable. We opted for bringing something on with us. I also didn’t like that I had to have T-mobile for online movies. Stupid.

Had to buy a snack box as I am gluten free. They should be free in extra comfort. Food they provided was awful. Not enough water stops.

You can standby to get on earlier flight if the seat is open.

it was good except the too big men in my personal space.

Free WiFi was awesome. I hate the five hour delayed take off.. arrrgh!

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Traveling to a place near Chicago?

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to O'ahu

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.