$231 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 9/2. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Maui

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, 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 Chicago to Maui, as well as popular online travel agencies
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Flights Deals

Best Maui Flight Deals from O'Hare Intl

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului1 stop$459
Kapalua
Kapalua2 stops$938
Hana
Hana2 stops$807
Kahului
Kahului1 stop$459
Kapalua
Kapalua2 stops$938
Hana
Hana2 stops$807

Cheap Flights from O'Hare Intl to Maui

 
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

Wed, Oct 15 - Wed, Oct 29
Alaska Airlines Logo
7:59 pm - 10:05 pmORD-OGG
31h 06m1 stop
Alaska Airlines Logo
10:59 pm - 1:54 pmOGG-ORD
9h 55m1 stop
$459Alaska Airlines
Find Deal
Mon, Nov 10 - Mon, Nov 17
Alaska Airlines Logo
7:55 pm - 2:32 pmORD-OGG
22h 37m1 stop
Alaska Airlines Logo
11:59 pm - 1:54 pmOGG-ORD
9h 55m1 stop
$460Alaska Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 27
American Airlines Logo
6:00 am - 1:55 pmORD-OGG
12h 55m1 stop
American Airlines Logo
9:46 pm - 3:55 pmOGG-ORD
13h 09m1 stop
$462American Airlines
Find Deal
Fri, Sep 19 - Tue, Sep 30
American Airlines Logo
6:00 am - 11:44 amORD-OGG
10h 44m1 stop
American Airlines Logo
5:54 pm - 9:26 amOGG-ORD
10h 32m1 stop
$463American Airlines
Find Deal
Fri, Sep 5 - Fri, Sep 12
Hawaiian Airlines Logo
6:20 am - 1:25 pmORD-OGG
12h 05m1 stop
Hawaiian Airlines Logo
12:45 pm - 7:03 amOGG-ORD
13h 18m1 stop
$465Hawaiian Airlines
Find Deal
Mon, Sep 29 - Mon, Oct 6
Delta Logo
7:10 am - 5:06 pmORD-OGG
14h 56m1 stop
Delta Logo
9:10 pm - 5:57 pmOGG-ORD
15h 47m2 stops
$466Delta
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
6:10 am - 5:08 pmORD-OGG
15h 58m2 stops
Delta Logo
9:10 pm - 5:30 pmOGG-ORD
15h 20m2 stops
$472Delta
Find Deal
Mon, Oct 13 - Fri, Oct 17
Hawaiian Airlines Logo
6:00 am - 1:28 pmORD-OGG
12h 28m1 stop
Hawaiian Airlines Logo
11:09 pm - 2:50 pmOGG-ORD
10h 41m1 stop
$498Hawaiian Airlines
Find Deal
Thu, Aug 14 - Thu, Aug 21
 Logo
1:03 pm - 4:33 pmORD-HNM
32h 30m2 stops
 Logo
4:55 pm - 7:03 amHNM-ORD
33h 08m2 stops
Tue, Aug 12 - Tue, Aug 19
 Logo
7:18 pm - 4:33 pmORD-HNM
26h 15m2 stops
 Logo
8:55 am - 2:24 pmHNM-ORD
24h 29m2 stops
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Maui.

The cheapest ticket to Maui from Chicago O'Hare Intl Airport found in the last 72 hours was to Kahului, at $903 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 $903.

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 $958, 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 October, when tickets cost $518 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,218 and $1,083 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 Wednesday, 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. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonApril
High seasonJanuary
Cheapest flight$231
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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 114% 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 $1,136.

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 10000 reviews
7.1Entertainment
8.5Crew
7.8Comfort
8.1Boarding
7.1Food
Airline reviews

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

10.0 ExcellentJeffrey, Jun 2025HNL - KOA
Read more Alaska Airlines reviews

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

Only issue was the 2 hr delay after an 8 hr layover. Very long day.

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.

Flight was delayed 5 hours. Missed connecting flight. Very little apology or attempt to make anything better. Got a $150 credit for next flight. There won’t be another flight. First time on Alaska - last time. Keep your credit. Should have done something more

Terrible check in experience, and they ended up losing our bag.

they didn't fix a plane and we were delayed travelling an extra 12 hours.

This flight was how a flight should be. The flight from Hawaii to Seattle was terrible

So much better coming back to Seattle than my trip TO Chicago. This crew actually communicated with the passengers!! Rebecca, one of the crew, stopped and visited with me about sign language. She should get a bonus of some kind!! She's a very neat gal!! It was still warm inside the plane, but it was packed! I still think you could do better than those teeny tiny pretzels! These were spicy and tasted terrible! All in all, still a better ride coming home. Go Seahawks!!

Arrival delay waiting for another flight to be towed and deboarded

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Check in process was a mess. Long lines, equipment malfuctioning. One line for baggage tags then a second line for bag checkin.

Boarding was chaotic. Microphone not working properly and second agent was distracted from task with baggage and late arrivals.

It was very pleasant. The staff and crew are very polite.

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

Bar code for checking luggage and boarding pass didn't work. Had to stand in long customer service line. Passengers at Oahu should be aware the Terminal for Hawaiian Air requires travel by shuttle. Budget an extra 20-30 minutes to get from the main terminal to the remote terminal.

Checking baggage at Honolulu was a real mess. No signs directing where to go.

We boarded an hour and a half late because a coffee maker leaked in the plane. Then we had to wait for awhile to get off the plane because another plane was in our spot at the terminal. I had plans when I landed that I had to skip so it was pretty disappointing.

We moved from the international terminal to a new location. I think there are still some bugs to work out . We didn’t receive check in notification and had to scramble to find it but i think it will work out

Not so good. The takeoff was aborted after reaching 100 knots due to a problem with the front tires. I do commend the pilot for a quick decision and preventing a potential disaster. We returned to the gate to put fresh tires on the front. Our flight was delayed for over 3 hours. The rest of the flight was okay. We were reimbursed by Hawaiian Airlines for only $50. Not too generous

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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