$170 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 2/26. 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 Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$342
Southwest
Thu 2/26Sun 3/1
HNL - MDW • 1 stop
Cheapest non-stop
$419
Typical prices: $716-$1,708
United Airlines
Wed 2/25Wed 3/4
HNL - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Useful Info
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, Feb 26 - Sun, Mar 1
Southwest Logo
9:55 pm - 6:20 pm
HNL
-
MDW
16h 25m
1 stop
Southwest Logo
10:50 am - 9:00 pm
MDW
-
HNL
14h 10m
1 stop
$342Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
9:55 pm - 1:40 pm
HNL
-
MDW
11h 45m
2 stops
Southwest Logo
10:50 am - 9:00 pm
MDW
-
HNL
14h 10m
1 stop
$348Southwest
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
10:55 pm - 1:14 pm
HNL
-
ORD
10h 19m
1 stop
United Airlines Logo
9:30 am - 2:54 pm
ORD
-
HNL
9h 24mnonstop
$372United Airlines
Thu, Feb 26 - Thu, Mar 5
United Airlines Logo
12:35 pm - 5:03 am
HNL
-
ORD
12h 28m
1 stop
United Airlines Logo
9:40 am - 3:04 pm
ORD
-
HNL
9h 24mnonstop
$381United Airlines
Wed, Apr 29 - Sat, May 2
Alaska Airlines Logo
10:00 pm - 7:03 pm
HNL
-
ORD
16h 03m
1 stop
Alaska Airlines Logo
8:48 pm - 11:05 am
ORD
-
HNL
19h 17m
1 stop
$383Alaska Airlines
Wed, Feb 25 - Wed, Mar 4
Alaska Airlines Logo
11:35 pm - 2:58 pm
HNL
-
ORD
11h 23m
1 stop
Alaska Airlines Logo
8:20 am - 7:59 pm
ORD
-
HNL
15h 39m
1 stop
$394Alaska Airlines
Tue, Mar 3 - Wed, Mar 11
Multiple Airlines Logo
11:35 pm - 2:58 pm
HNL
-
ORD
11h 23m
1 stop
Multiple Airlines Logo
7:00 am - 9:01 pm
ORD
-
HNL
19h 01m
2 stops
$407Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
8:11 am - 11:59 pm
HNL
-
ORD
11h 48m
1 stop
Multiple Airlines Logo
3:07 pm - 10:58 am
ORD
-
HNL
23h 51m
2 stops
$408Multiple Airlines
Wed, Apr 29 - Sun, May 3
Delta Logo
3:15 pm - 8:47 am
HNL
-
MDW
12h 32m
1 stop
Delta Logo
6:00 am - 1:45 pm
MDW
-
HNL
12h 45m
1 stop
$424Delta
Wed, Apr 29 - Sun, May 3
Delta Logo
4:10 pm - 12:43 pm
HNL
-
MDW
15h 33m
2 stops
Delta Logo
6:00 am - 1:45 pm
MDW
-
HNL
12h 45m
1 stop
$430Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$170
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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.
8.0
Alaska AirlinesOverall score based on 11810 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.0Entertainment
7.1Food
Airline reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

I paid for WiFi but it never really worked. That was frustrating.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

I flew Hawaiian Airlines three times during my trip. Each time, when we went to baggage claim, it took about 45 minutes to an hour to receive our luggage.

The kiosk was fast. I got in and got my baggage tag right away. There was a long lines at baggaged check in But it moved fast and checked my baggage with no problem. The flight was good. The flight attendants were very helpful, friendly and always smiling.

We were very late to take off, late exit plane, and luggage took a long time.

Boarding passes could not be received online, even after online check-in. While they appeared on the Alaska.com app, they did not transfer to inbox or messages and were not available at all on the Alaska.com app following the check-in process. There was no choice other than to get boarding passes at the airport counter.

Alaska Airlines has horrible customer service. After sitting in a packed airplane for over an hour, they decided to cancel our flight and had us deplane. Instead of helping us nearby, we had to ride two trains (in Seattle Airport), from the S-Gates to the C-Gates; only to stand in a line for 3 and a half hours. Throughout the 3 hours, there was often 1 agent at the customer service counter to help the passengers trying to get information and accommodation on a flight that they cancelled. Do better!

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.

I know airlines have to save money, but a little more legroom would be nice. I’m a small person and I just felt cramped after a few hours. However, I loved everything else! Free Alaska Airlines wifi, free movies, yummy snacks, and the crew was so helpful and accommodating!

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.