$181 Find Cheap Flights from Chicago O'Hare Airport to Maui

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Maui departing on 2/8. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui.
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Cheap Flights from O'Hare Intl to Maui

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului2 stops$428
Kapalua
Kapalua3 stops$875
Kahului
Kahului2 stops$428
Kapalua
Kapalua3 stops$875

Book Cheap O'Hare Intl to Maui Plane Tickets

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

Mon, Jan 12 - Tue, Jan 20
Delta Logo
7:30 am - 7:15 pmORD-OGG
15h 45m2 stops
Delta Logo
2:02 pm - 8:40 amOGG-ORD
14h 38m2 stops
$428Delta
Find Deal
Fri, Jan 30 - Sun, Feb 8
Delta Logo
5:30 am - 3:37 pmORD-OGG
14h 07m1 stop
Delta Logo
10:00 pm - 1:22 pmOGG-ORD
11h 22m1 stop
$429Delta
Find Deal
Sat, Dec 6 - Mon, Dec 8
Alaska Airlines Logo
5:51 pm - 10:53 pmORD-OGG
33h 02m1 stop
Alaska Airlines Logo
1:52 pm - 7:54 pmOGG-ORD
26h 02m1 stop
$430Alaska Airlines
Find Deal
Mon, Jan 12 - Sun, Jan 18
Delta Logo
7:30 am - 7:15 pmORD-OGG
15h 45m2 stops
Delta Logo
10:00 pm - 1:22 pmOGG-ORD
11h 22m1 stop
$432Delta
Find Deal
Thu, Feb 5 - Wed, Feb 11
Alaska Airlines Logo
2:06 pm - 6:17 amORD-OGG
20h 11m2 stops
Alaska Airlines Logo
6:00 am - 11:37 pmOGG-ORD
13h 37m2 stops
$433Alaska Airlines
Find Deal
Fri, Dec 12 - Thu, Dec 18
Alaska Airlines Logo
8:55 am - 11:40 pmORD-OGG
18h 45m1 stop
Alaska Airlines Logo
3:52 pm - 8:02 pmOGG-ORD
24h 10m1 stop
$434Alaska Airlines
Find Deal
Sun, Jan 25 - Fri, Jan 30
Alaska Airlines Logo
8:00 am - 11:20 pmORD-OGG
19h 20m1 stop
Alaska Airlines Logo
11:59 pm - 2:29 pmOGG-ORD
10h 30m1 stop
$435Alaska Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
Multiple Airlines Logo
9:06 pm - 12:19 pmORD-OGG
19h 13m1 stop
Multiple Airlines Logo
4:04 pm - 6:05 amOGG-ORD
34h 01m1 stop
$437Multiple Airlines
Find Deal
Sun, Jan 25 - Fri, Jan 30
Delta Logo
7:30 am - 6:04 pmORD-OGG
14h 34m1 stop
Delta Logo
10:00 pm - 4:59 pmOGG-ORD
14h 59m2 stops
$439Delta
Find Deal
Sat, Jan 31 - Sun, Feb 8
Alaska Airlines Logo
9:00 am - 6:51 amORD-OGG
25h 51m2 stops
Alaska Airlines Logo
11:00 pm - 11:50 pmOGG-ORD
20h 50m1 stop
$440Alaska Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Maui flights

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

What is the cheapest Chicago O'Hare Intl Airport to Maui flight route?

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

The cheapest ticket to Maui from Chicago O'Hare Intl Airport found in the last 72 hours was to Kahului, at $622 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Kahului (OGG), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $622.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Maui?

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 $421, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Maui?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Maui, 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 O'Hare Intl Airport to Maui is January, when tickets cost $660 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,199 and $1,097 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Maui?

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

If you are looking for a flight deal from Chicago O'Hare Airport to Maui, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Maui, Wednesday is the cheapest day to fly and Saturday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Maui?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Maui, 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 O'Hare Intl Airport to Maui, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$181
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 33% increase in price.
Flight from Chicago O'Hare Airport to Kahului

FAQs - booking Maui flights

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

    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 O'Hare Airport to Maui.

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

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

    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 O'Hare Airport to Maui 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 O'Hare Airport to Maui?

    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 O'Hare Airport to Maui 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 Maui?

    The cheapest time of day to fly to Maui is generally in the evening, when round-trip flights cost $531 on average. Morning departures are around 106% more expensive than evening flights, on average. The most expensive time of day to fly to Maui is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,094.

Reviews of the top 5 airlines serving from O'Hare Intl to Maui

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maui. 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 O'Hare Intl to Maui? 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 11317 reviews
8.5Crew
7.1Food
8.1Boarding
7.0Entertainment
7.8Comfort
Airline reviews

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.

8.0 ExcellentAnonymous, Nov 2025PHX - HNL
Read more Alaska Airlines reviews

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.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

It was fine. It was a 30 minute flight so there was water or fruit juice and no food. Which was totally fine. The check in, gate and flight crew were all excellent.

I didn’t order food so can’t really say how it was. Overall, it was a great experience.

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use

Glad they offer free meal, & I got a complimentary drink I’d like coffee,tea, or water offered 3/4 into trip

Could not check in online. Called airline twice, thinking Hawaiian Airlines could check me in during phone call. NO. In 2nd phone call, Customer Service explained that due to “transition period” of Hawaiian Airlines/Alaska Airlines merger, I could only check in at the airport. In addition, flight to Kahului was late at arrival gate; I made connection to Lihue but my bag did not, so I had to return to Lihue airport a couple hours after my arrival to retrieve the bag.

My flight got canceled never left san diego and miss out my fam event

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I always love flying Hawaii and I have nothing to add

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

I was very, very cold and a stranger loaned me her sweater next to me. I didn’t wanna buy a blanket just for a four hour trip when I did not need the pillow or the earphones. I don’t mind purchasing a blanket, but I only needed that not all of it accessories. Cold air pretty much blew the entire trip. Two people in front of me both bought the blanket packages. Maybe that’s the idea. The crew was exceptionally nice and passed through multiple times.. the restrooms were very clean and usually accessible.

3 hour wait on customer service after flight was cancelled. Was bumped to a flight where I wouldnt have gotten to my destination for another 2 days. Had to fully refund flight and book a new one the following morning. Paid twice the amount for the flight than I had originally booked. Very disappointed I was not offered any sort of discount or points for all of the frustration, in fact the airline profited twice as much off of me by cancelling my flight and and changing my entire trip.

Very accommodating on flight changes when something came up. Definitely felt a notch above other airlines.

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Everything you need to know for your flight to Maui

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