OGG - CHI

$258 Find Cheap Flights from Kahului 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 from Kahului to Chicago departing on 5/20. 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.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kahului to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kahului to Chicago, as well as popular online travel agencies
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Cheap Flights from Kahului to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kahului 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.

Recent round-trip flight deals from Kahului to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Kahului to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Alaska Airlines Logo
9:46 pm - 11:56 pmOGG-ORD
21h 10m1 stop
Alaska Airlines Logo
7:00 am - 8:46 pmORD-OGG
18h 46m1 stop
$543Alaska Airlines
Find Deal
Tue, May 20 - Tue, May 27
Alaska Airlines Logo
9:46 pm - 11:56 pmOGG-ORD
21h 10m1 stop
Alaska Airlines Logo
7:00 am - 10:13 pmORD-OGG
20h 13m2 stops
$553Alaska Airlines
Find Deal
Tue, May 20 - Tue, May 27
Alaska Airlines Logo
9:45 pm - 10:23 pmOGG-ORD
19h 38m2 stops
Alaska Airlines Logo
6:00 am - 1:40 pmORD-OGG
12h 40m1 stop
$601Alaska Airlines
Find Deal
Thu, Jun 5 - Mon, Jul 28
Alaska Airlines Logo
11:55 am - 10:23 pmOGG-ORD
29h 28m1 stop
Alaska Airlines Logo
6:00 am - 1:40 pmORD-OGG
12h 40m1 stop
$635Alaska Airlines
Find Deal
Thu, Jun 5 - Mon, Jul 28
Delta Logo
9:30 pm - 6:20 pmOGG-ORD
15h 50m2 stops
Delta Logo
8:40 am - 7:25 pmORD-OGG
15h 45m2 stops
$646Delta
Find Deal
Tue, May 20 - Tue, May 27
Alaska Airlines Logo
9:46 pm - 1:08 pmOGG-ORD
10h 22m1 stop
Alaska Airlines Logo
3:17 pm - 10:13 pmORD-OGG
11h 56m1 stop
$664Alaska Airlines
Find Deal
Sat, May 24 - Sat, May 31
Hawaiian Airlines Logo
10:34 pm - 4:59 pmOGG-ORD
13h 25m1 stop
Hawaiian Airlines Logo
1:03 pm - 9:34 pmORD-OGG
13h 31m1 stop
$665Hawaiian Airlines
Find Deal
Tue, Jun 24 - Wed, Jul 30
Hawaiian Airlines Logo
9:39 pm - 1:07 pmOGG-ORD
10h 28m1 stop
Hawaiian Airlines Logo
2:03 pm - 8:39 pmORD-OGG
11h 36m1 stop
$715Hawaiian Airlines
Find Deal
Wed, Jul 9 - Mon, Jul 14
Delta Logo
9:30 pm - 6:45 pmOGG-MDW
16h 15m2 stops
Delta Logo
9:20 am - 7:25 pmMDW-OGG
15h 05m2 stops
$822Delta
Find Deal
Thu, May 15 - Mon, May 19
Delta Logo
8:50 pm - 4:45 pmOGG-ORD
14h 55m2 stops
Delta Logo
7:10 am - 7:25 pmORD-OGG
17h 15m2 stops
$822Delta
Find Deal
Thu, May 15 - Mon, May 19
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KAYAK's insights & trends for Kahului to Chicago flights

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

What is the cheapest Kahului to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Kahului to Chicago.

Our data shows that the cheapest route for a return flight from Kahului to Chicago cost $467 and was between Kahului (OGG) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $467.

What’s the cheapest day of the week to fly from Kahului to Chicago?

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

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Kahului to Chicago. For your return ticket, we recommend flying on a Monday and avoiding Wednesdays for the best deals.

What is the cheapest month to fly from Kahului to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Kahului to Chicago, 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 Kahului to Chicago is January, where tickets cost $403 (return) on average. On the other hand, the most expensive months are April and June, where the average cost of round-trip tickets is $1,013 and $831 respectively.

Can I save money by flying with a layover from Kahului to Chicago?

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 $1,737, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$258
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Kahului to Chicago O'Hare Airport

When to book flights from Kahului to Chicago

Are your dates flexible? Find out the best times to travel from Kahului to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Kahului to Chicago

  • What is the cheapest flight from Kahului to Chicago?

    In the last 3 days, the lowest price for a flight from Kahului to Chicago was $258 for a one-way ticket and $543 for a round-trip.

  • Do I need a passport to fly between Kahului and Chicago?

    A passport is not required to fly from Kahului to Chicago.

  • Which airports will I be using when flying from Kahului to Chicago?

    On your way to Chicago, you’ll fly out from Kahului. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Kahului to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the Kahului to Chicago flight route.

  • Which aircraft models fly most regularly from Kahului to Chicago?

    The Boeing 767-300 (winglets) is the aircraft model that flies most regularly on the Kahului to Chicago flight route.

  • Which airline alliances offer flights from Kahului to Chicago?

    Star Alliance is the only airline alliance operating flights between Kahului and Chicago.

  • On which days can I fly direct from Kahului to Chicago?

    You can catch a nonstop flight from Kahului to Chicago on on Saturday.

  • Which is the best airline for flights from Kahului to Chicago, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Kahului to Chicago are Alaska Airlines and United Airlines. With an average price for the route of $721 and an overall rating of 8.0, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $555 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Kahului 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 Kahului to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kahului 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 Kahului 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 Kahului with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kahului 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 Kahului up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Kahului to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $465 or less one-way and $560 or less round-trip.

Prefer to fly direct from Kahului to Chicago?

Find which airlines fly direct from Kahului Airport to Chicago, which days they fly and book direct flights.

Direct departures

Kahului to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Kahului

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 3 airlines serving from Kahului to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Kahului to Chicago. 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 Kahului 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 9968 reviews
7.1Entertainment
7.9Comfort
8.2Boarding
8.5Crew
7.1Food
Airline reviews

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

2.0 MediocreJános, Apr 2025KOA - OGG
Read more Alaska Airlines reviews

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

Self check in is not indicated well if you approach Terminal 1 from Terminal 2 Parking

1.5 hour delay boarding plus 1+ hour sitting in plane waiting for ground crew to load luggage and freight, made for 3:00AM arrival in Seattle.

The plane was freezing and no blanquets available unless you buy them. My screen was bad so I couldn’t watch any entertainment.

Great service, great options, flight was bumpy so didn't get second beverage service and everything was communicated very clearly and courteously. No notes: everyone did great! Also loved the fun Hawaiian drink options (non-alcoholic).

While the flight itself was pleasant, the process of checking in was difficult. The line was long and our connection time was but two hours. When we finally got to the Hawaiian agent and told him that we were traveling on Alaskan Airlines, he told us we would need to go to a different terminal. I told him that another Hawaiian Airlines agent had directed us to him. I’m looking at our tickets, he noticed that the Alaskan Airlines flight was to be managed by a second party. He ended admonish us for not telling us so Rather than considering that we might’ve been right in the first place.

We had to cancel and we’re treated fairly with 100%refund quickly

Plane left an hour late due to flight staffing problems. Only a 45 min flight, but it took 3 hours as a result, which left a lot of people disgruntled. No excuses. No recompense.

Probably the worst 1st Class I have ever experienced. Sam, our flight attendant, was excellent. Other than that, everything from the Alaska Longe experience to the buggy app to the uncomfortable flight and uncommunicative agents were poor. The agent who booked us in forgot to mark TSA PreCheck on our boarding passes and we had to go back to get this done. They were a cut below every other airline we have experienced in just about every area.

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight boarded from Gate 39 at OGG, the farthest gate in the terminal. There were no Hawaiian themed amenities for the flight. The first class service was mediocre at best; I received not special welcome or recognition as an executive platinum member of American Advantage program. The flight attendants were more concerned with their cell phones than saying "thank you" to the passengers as we disembarked. Fortunately, the flight arrived at LAX a few minutes early.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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