$188 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 4/20. 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.
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$466
Kapalua
Kapalua2 stops$792
Hana
Hana2 stops$877
Kahului
Kahului2 stops$466
Kapalua
Kapalua2 stops$792
Hana
Hana2 stops$877

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

Wed, Apr 8 - Wed, Apr 15
Multiple Airlines Logo
3:29 pm - 9:30 am
ORD
-
OGG
23h 01m
2 stops
Multiple Airlines Logo
3:10 pm - 5:50 am
OGG
-
ORD
33h 40m
1 stop
$466Multiple Airlines
Sat, May 2 - Thu, May 7
Alaska Airlines Logo
8:50 am - 8:52 pm
ORD
-
OGG
17h 02m
1 stop
Alaska Airlines Logo
10:51 pm - 11:43 pm
OGG
-
ORD
19h 52m
1 stop
$467Alaska Airlines
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
7:45 pm - 11:17 am
ORD
-
OGG
20h 32m
1 stop
Multiple Airlines Logo
5:35 pm - 5:35 am
OGG
-
ORD
31h 00m
2 stops
$468Multiple Airlines
Wed, Apr 15 - Sun, Apr 19
Alaska Airlines Logo
4:10 pm - 10:02 pm
ORD
-
OGG
34h 52m
1 stop
Alaska Airlines Logo
11:02 pm - 11:59 pm
OGG
-
ORD
19h 57m
1 stop
$472Alaska Airlines
Sun, May 3 - Fri, May 8
Delta Logo
7:15 am - 5:36 pm
ORD
-
OGG
15h 21m
1 stop
Delta Logo
9:00 pm - 1:54 pm
OGG
-
ORD
11h 54m
1 stop
$473Delta
Tue, Apr 21 - Fri, Apr 24
Multiple Airlines Logo
8:20 am - 10:02 pm
ORD
-
OGG
18h 42m
1 stop
Multiple Airlines Logo
10:40 am - 6:40 am
OGG
-
ORD
15h 00m
2 stops
$474Multiple Airlines
Fri, May 1 - Thu, May 7
Alaska Airlines Logo
8:50 am - 8:52 pm
ORD
-
OGG
17h 02m
1 stop
Alaska Airlines Logo
10:51 pm - 11:43 pm
OGG
-
ORD
19h 52m
1 stop
$475Alaska Airlines
Sat, Apr 25 - Tue, Apr 28
Multiple Airlines Logo
8:48 pm - 11:37 am
ORD
-
OGG
19h 49m
1 stop
Multiple Airlines Logo
10:40 am - 6:40 am
OGG
-
ORD
15h 00m
2 stops
$476Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
8:20 am - 8:25 pm
ORD
-
OGG
17h 05m
2 stops
Multiple Airlines Logo
11:02 pm - 6:40 pm
OGG
-
ORD
14h 38m
1 stop
$477Multiple Airlines
Sun, May 10 - Wed, May 13
Delta Logo
8:42 am - 7:35 pm
ORD
-
OGG
15h 53m
2 stops
Delta Logo
9:00 pm - 11:57 pm
OGG
-
ORD
21h 57m
1 stop
$478Delta
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 $734 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 $734.

What is the cheapest time of day to fly to Maui?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Maui depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Maui is generally in the morning, when round-trip flights cost $1,096 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 $1,096.

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 $431, 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 September, when tickets cost $654 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,201 and $1,035 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, Thursday is the cheapest day to fly and Friday 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 4 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$188
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 27% 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.

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 12029 reviews
8.1Boarding
7.8Comfort
7.0Entertainment
8.5Crew
7.1Food
Airline reviews

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

10.0 ExcellentAnonymous, Feb 2026
LAX - LIH
Read more Alaska Airlines reviews

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

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.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

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.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

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. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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.

Everything you need to know for your flight to Maui

Information on your arrival and departure airports