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$211 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 11/7. 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
Wed 7/10
Wed 7/17

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Good to know

Low season

January

High season

June

Cheapest flight

$211
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 21% increase in price.
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.

See more FAQs

Prefer to fly non-stop from O'ahu to Chicago?

Find which airlines fly direct from O'ahu to Chicago, which days they fly and book direct flights.

Nonstop departures

O'ahu to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights

Nonstop returns

Chicago to O'ahu

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights
See more direct flights

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.
8.0
Alaska AirlinesOverall score based on 9254 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.3Entertainment
7.3Food
Airline reviews

The TSA line took over an hour and half to get through due to being understaffed and only having one scanner open. I got to my gate with five minutes to spare only to find out my flight left 8 minutes early. I needed help rebooking and had to pay to get a new ticket and was grounded for 24 hours. Not the greatest experience to start things off and had to completely rework my trip to accommodate the situation.

2.0 MediocreAnonymous, Jun 2024GEG - BOI
Read more about Alaska Airlines reviews

The TSA line took over an hour and half to get through due to being understaffed and only having one scanner open. I got to my gate with five minutes to spare only to find out my flight left 8 minutes early. I needed help rebooking and had to pay to get a new ticket and was grounded for 24 hours. Not the greatest experience to start things off and had to completely rework my trip to accommodate the situation.

Mediocre is best way to describe. Bare bones narrow seats, Dirty pulldown tray, unfriendly cabin crew who were in a hurry to serve tiny drinks and tiny snacks. (Compared to much better Hawaiian Airlines experience, .. no comparison!)

Plane was very cold, but other than that, it was a perfect flight

The airline itself was extremely comfortable and the staff were wonderful. The communication was excellent amongst the pilots and flight attendants and the passengers. I was throughly impressed by the cleaning crew that came on the plane immediately to ready it for the next flight. I have flown a bunch of times post Covid pandemic and have never seen this! I gave the “okay” rating for the food and entertainment because I didn’t order food and there wasn’t entertainment offered through the plane (only your personal devices).

1309 on May had some very bumpy segments that seem to take too long to get to smoother air. My initial flight out of GRR was delayed and missed connections. Sure glad I made a different one in ORD so I could be in Anchorage.

It was warm on the plane. Perhaps the people who were coughing quite often should be encouraged to wear a mask?! It was a long 4 hours.

Flight was late but crew was very efficient and friendly.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Was not happy that we had to wait an additional 50 minutes for passengers that were still in TSA. This delay made us miss our connecting flight in Seattle to get home to tuck in our two little toddlers. We ran off the plane and ran across the entire airport trying to make this flight only to get to the gate to see that they have ended boarding. So they were willing to wait for passengers in Hawaii but not Seattle?? Especially when this wasn't even our fault. I expect to receive miles for missing our flight and spending an additional 4 hours in Seattle.

I usually choose Alaska Airlines over any other airline. They try the hardest to make flying a great experience.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Book cheap flights from O'ahu to Chicago

Recent round-trip flight deals

9/17Tue
1 stopAlaska Airlines
21h 57mHNL-ORD
9/24Tue
1 stopAlaska Airlines
25h 45mORD-HNL
$416
9/26Thu
1 stopAmerican Airlines
11h 18mHNL-ORD
9/27Fri
2 stopsAmerican Airlines
14h 47mORD-HNL
$421
9/17Tue
2 stopsDelta
13h 56mHNL-ORD
9/24Tue
2 stopsDelta
16h 42mORD-HNL
$432
9/17Tue
1 stopDelta
14h 05mHNL-ORD
9/24Tue
2 stopsDelta
14h 08mORD-HNL
$451
8/26Mon
2 stopsDelta
12h 44mHNL-ORD
8/28Wed
2 stopsDelta
18h 48mORD-HNL
$456
8/23Fri
1 stopAmerican Airlines
16h 52mHNL-ORD
8/28Wed
1 stopAmerican Airlines
13h 53mORD-HNL
$480
9/10Tue
2 stopsDelta
13h 56mHNL-ORD
9/18Wed
2 stopsDelta
16h 42mORD-HNL
$482
8/18Sun
1 stopAlaska Airlines
27h 45mHNL-ORD
8/26Mon
1 stopAlaska Airlines
20h 45mORD-HNL
$489
7/17Wed
1 stopUnited Airlines
16h 56mHNL-ORD
7/29Mon
2 stopsUnited Airlines
19h 07mORD-HNL
$800
8/8Thu
1 stopUnited Airlines
34h 35mHNL-ORD
8/15Thu
nonstopUnited Airlines
9h 00mORD-HNL
$819

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Recent one-way flight deals

11/7Thu
1 stopDelta
12h 05mHNL-MDW
$211
9/18Wed
1 stopAmerican Airlines
12h 38mHNL-ORD
$211
11/4Mon
2 stopsDelta
16h 03mHNL-MDW
$216
8/13Tue
2 stopsDelta
13h 55mHNL-ORD
$216
8/22Thu
3 stops
17h 29mHNL-ORD
$254
8/11Sun
1 stopAlaska Airlines
27h 45mHNL-ORD
$284
7/3Wed
2 stopsAlaska Airlines
33h 35mHNL-ORD
$292
8/22Thu
2 stops
17h 04mHNL-ORD
$300
7/17Wed
1 stopUnited Airlines
17h 58mHNL-ORD
$349
8/24Sat
1 stopUnited Airlines
24h 44mHNL-ORD
$392

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Last minute flights from O'ahu to Chicago

Last minute flight, train and bus deals

6/14Fri
multi-stopAmerican Airlines
11h 42mHNL-ORD
6/21Fri
multi-stopAmerican Airlines
13h 20mORD-HNL
$776
6/14Fri
multi-stopAmerican Airlines
11h 42mHNL-ORD
6/21Fri
multi-stopAmerican Airlines
15h 34mORD-HNL
$921
6/14Fri
multi-stopAmerican Airlines
14h 40mHNL-ORD
6/21Fri
multi-stopAmerican Airlines
14h 36mORD-HNL
$1,157
6/14Fri
multi-stopUnited Airlines
11h 03mHNL-ORD
6/21Fri
nonstopUnited Airlines
9h 00mORD-HNL
$1,217
6/14Fri
multi-stopDelta
12h 28mHNL-MDW
6/21Fri
multi-stopDelta
16h 21mMDW-HNL
$1,217
6/14Fri
multi-stopDelta
15h 04mHNL-MDW
6/21Fri
multi-stopDelta
16h 21mMDW-HNL
$1,222
6/14Fri
nonstopUnited Airlines
8h 03mHNL-ORD
6/21Fri
nonstopUnited Airlines
9h 00mORD-HNL
$1,372
6/14Fri
multi-stopDelta
12h 28mHNL-MDW
6/21Fri
multi-stopDelta
12h 32mMDW-HNL
$1,482

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Flights to Chicago

Return flight deals:

Chicago - O'ahu

Cabin classes:

$360
$232
$231
$44