$256 Find Cheap Flights from Chicago to O'ahu

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to O'ahu departing on 8/18. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to O'ahu

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to O'ahu.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to O'ahu.
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Flight Deals

Book Cheap Chicago to O'ahu Plane Tickets

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

Wed, Sep 2 - Tue, Sep 8
Delta Logo
7:30 am - 8:47 pm
ORD
-
HNL
18h 17m
2 stops
Delta Logo
3:35 pm - 12:41 pm
HNL
-
ORD
16h 06m
1 stop
$616Delta
Wed, Sep 23 - Wed, Sep 30
Multiple Airlines Logo
6:00 am - 9:08 pm
ORD
-
HNL
20h 08m
2 stops
Multiple Airlines Logo
8:00 am - 6:20 am
HNL
-
ORD
17h 20m
2 stops
$620Multiple Airlines
Wed, Sep 2 - Tue, Sep 8
Delta Logo
7:30 am - 8:47 pm
ORD
-
HNL
18h 17m
2 stops
Delta Logo
4:05 pm - 12:39 pm
HNL
-
ORD
15h 34m
2 stops
$621Delta
Thu, Sep 24 - Wed, Sep 30
Multiple Airlines Logo
8:00 am - 4:48 pm
ORD
-
HNL
13h 48m
1 stop
Multiple Airlines Logo
8:00 am - 6:20 am
HNL
-
ORD
17h 20m
2 stops
$625Multiple Airlines
Mon, Sep 21 - Fri, Sep 25
Delta Logo
6:00 pm - 11:40 am
ORD
-
HNL
22h 40m
2 stops
Delta Logo
9:59 pm - 11:45 pm
HNL
-
ORD
20h 46m
1 stop
$626Delta
Thu, Sep 24 - Tue, Sep 29
Multiple Airlines Logo
2:22 pm - 8:30 pm
ORD
-
HNL
11h 08m
1 stop
Multiple Airlines Logo
12:45 pm - 6:20 am
HNL
-
ORD
12h 35m
1 stop
$627Multiple Airlines
Thu, Oct 29 - Tue, Nov 3
Multiple Airlines Logo
7:20 am - 2:20 pm
ORD
-
HNL
12h 00m
1 stop
Multiple Airlines Logo
11:59 pm - 5:37 pm
HNL
-
ORD
13h 38m
1 stop
$628Multiple Airlines
Wed, Aug 12 - Mon, Aug 17
Alaska Airlines Logo
6:20 am - 7:03 pm
ORD
-
HNL
17h 43m
1 stop
Alaska Airlines Logo
9:55 pm - 6:57 pm
HNL
-
ORD
16h 02m
1 stop
$630Alaska Airlines
Mon, Sep 21 - Mon, Sep 28
Southwest Logo
6:15 am - 12:35 pm
MDW
-
HNL
11h 20m
1 stop
Southwest Logo
8:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$637Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
12:00 pm - 9:20 pm
MDW
-
HNL
14h 20m
2 stops
Southwest Logo
8:15 am - 5:55 am
HNL
-
MDW
16h 40m
2 stops
$640Southwest
Booking Insights

KAYAK's insights & trends for Chicago to O'ahu flights

Get data-powered insights and trends into flights from Chicago to O'ahu to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to O'ahu flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to O'ahu from Chicago found in the last 7 days was to Honolulu, at $678 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Honolulu (HNL), and the cheapest round-trip airline ticket found on this route in the last 7 days was $678.

What is the cheapest time of day to fly to O'ahu?

The average price for all round-trip flights from Chicago to O'ahu depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to O'ahu is generally in the morning, when round-trip flights cost $898 on average. The most expensive time of day to fly to O'ahu is generally in the morning, which is peak travel time and where the average cost of a ticket is $898.

Can I save money by flying with a layover from Chicago to O'ahu?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $458, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to O'ahu?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to O'ahu, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to O'ahu is September, when tickets cost $232 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $2,149 and $1,509 respectively.

What’s the cheapest day of the week to fly from Chicago to O'ahu?

The average price of all round-trip flights from Chicago to O'ahu clicked on KAYAK for each day over the last 12 months.

For Chicago to O'ahu, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from O'ahu back to Chicago, the best deals are generally found on Wednesday, with Saturday being the most expensive.

How far in advance should I book a flight from Chicago to O'ahu?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to O'ahu, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to O'ahu, you should book around 4 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$256
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to Honolulu

FAQs - booking O'ahu flights

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

    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 Chicago to O'ahu.

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

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

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

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

    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 from Chicago to 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 Chicago to O'ahu

 
See real verified KAYAK customer reviews for airlines flying from Chicago to O'ahu. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to O'ahu? 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 12407 reviews
7.8Comfort
7.0Entertainment
8.1Boarding
8.5Crew
7.0Food
Airline reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

10.0 ExcellentAnonymous, May 2026
SEA - LIH
Read more Alaska Airlines reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

The crew seem untrained and uncertain no one ever checked up on us in our first class cabin. I had to ask for water four times and the lady kept saying she was busy when they weren't really doing anything. Had to walk to the back of the plane to get water for myself. Crew seem new and unexperience. You can tell this by the fumbling they kept making trying to fight. (I miss Hawaiian air.)

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

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

Thanks for all you do to keep us safe and on time!

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight to O'ahu

Cabin class types available on flights to Chicago

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.