$215 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 4/17. 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

Mon, Apr 27 - Tue, May 5
United Airlines Logo
1:18 pm - 7:49 pm
ORD
-
HNL
11h 31m
1 stop
United Airlines Logo
9:40 pm - 1:15 pm
HNL
-
ORD
10h 35m
1 stop
$392United Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
7:21 pm - 9:59 am
ORD
-
HNL
19h 38m
1 stop
Multiple Airlines Logo
7:50 am - 5:50 am
HNL
-
ORD
17h 00m
1 stop
$393Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Alaska Airlines Logo
8:20 am - 6:59 pm
ORD
-
HNL
15h 39m
1 stop
Alaska Airlines Logo
10:35 pm - 2:21 pm
HNL
-
ORD
10h 46m
1 stop
$394Alaska Airlines
Tue, Apr 7 - Tue, Apr 14
Multiple Airlines Logo
5:15 pm - 11:59 pm
ORD
-
HNL
35h 44m
2 stops
Multiple Airlines Logo
10:31 pm - 5:50 am
HNL
-
ORD
26h 19m
1 stop
$395Multiple Airlines
Sat, Apr 11 - Fri, Apr 17
Multiple Airlines Logo
5:53 pm - 9:59 am
ORD
-
HNL
21h 06m
2 stops
Multiple Airlines Logo
1:10 pm - 7:00 am
HNL
-
ORD
12h 50m
1 stop
$396Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
Multiple Airlines Logo
9:45 am - 11:59 pm
ORD
-
HNL
19h 14m
2 stops
Multiple Airlines Logo
10:31 pm - 5:50 am
HNL
-
ORD
26h 19m
1 stop
$397Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
7:45 pm - 9:59 am
ORD
-
HNL
19h 14m
1 stop
Multiple Airlines Logo
10:31 pm - 3:42 pm
HNL
-
ORD
12h 11m
1 stop
$398Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Southwest Logo
10:15 am - 9:10 pm
MDW
-
HNL
15h 55m
1 stop
Southwest Logo
11:55 am - 5:55 am
HNL
-
MDW
13h 00m
1 stop
$401Southwest
Wed, Apr 29 - Mon, May 4
Southwest Logo
11:45 am - 9:00 pm
MDW
-
HNL
14h 15m
2 stops
Southwest Logo
11:55 am - 5:25 am
HNL
-
MDW
12h 30m
1 stop
$407Southwest
Mon, Apr 13 - Tue, Apr 21
Delta Logo
9:31 am - 9:45 pm
MDW
-
HNL
17h 14m
2 stops
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
$430Delta
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 72 hours was to Honolulu, at $377 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 72 hours was $377.

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 $413, 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 January, when tickets cost $594 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $913 and $908 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 Friday 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 3 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$215
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 4% 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.

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

    The cheapest time of day to fly to O'ahu is generally in the morning, when round-trip flights cost $969 on average. The most expensive time of day to fly to O'ahu is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,290.

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.
8.0
Alaska AirlinesOverall score based on 11874 reviews
7.1Food
8.1Boarding
7.0Entertainment
7.8Comfort
8.5Crew
Airline reviews

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

2.0 MediocreIan, Feb 2026
ANC - HNL
Read more Alaska Airlines reviews

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

I behave had better flights this one was old and poor

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

No wheel chair as requested at Atlanta arrival on first flight.

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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.