ORD

$185 Find Cheap Flights from Maui to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 4/21. 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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Flight Deals

Cheap Flights from Maui to O'Hare Intl

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

Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
3:10 pm - 5:50 am
OGG
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ORD
33h 40m
1 stop
Multiple Airlines Logo
7:35 am - 11:17 am
ORD
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OGG
32h 42m
2 stops
$406Multiple Airlines
Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
3:10 pm - 5:50 am
OGG
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ORD
33h 40m
1 stop
Multiple Airlines Logo
2:00 pm - 11:17 am
ORD
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OGG
26h 17m
1 stop
$438Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
American Airlines Logo
3:03 pm - 6:47 am
OGG
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ORD
10h 44m
1 stop
American Airlines Logo
1:18 pm - 7:56 pm
ORD
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OGG
11h 38m
1 stop
$448American Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
11:45 am - 5:50 am
OGG
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ORD
37h 05m
2 stops
Multiple Airlines Logo
7:56 pm - 11:17 am
ORD
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OGG
20h 21m
1 stop
$453Multiple Airlines
Thu, May 7 - Mon, May 11
Alaska Airlines Logo
10:51 pm - 11:43 pm
OGG
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ORD
19h 52m
1 stop
Alaska Airlines Logo
7:59 pm - 8:52 pm
ORD
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OGG
29h 53m
1 stop
$454Alaska Airlines
Mon, Apr 27 - Wed, May 6
Alaska Airlines Logo
10:51 pm - 7:03 pm
OGG
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ORD
15h 12m
1 stop
Alaska Airlines Logo
8:50 am - 10:20 pm
ORD
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OGG
18h 30m
2 stops
$458Alaska Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
9:48 pm - 1:07 pm
OGG
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ORD
10h 19m
1 stop
American Airlines Logo
5:00 am - 2:01 pm
ORD
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OGG
14h 01m
1 stop
$460American Airlines
Thu, Apr 16 - Tue, Apr 21
Delta Logo
10:30 pm - 6:04 pm
OGG
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ORD
14h 34m
2 stops
Delta Logo
7:15 am - 5:36 pm
ORD
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OGG
15h 21m
1 stop
$468Delta
Mon, Apr 27 - Wed, May 6
Delta Logo
9:15 pm - 7:52 pm
OGG
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ORD
17h 37m
2 stops
Delta Logo
8:50 am - 7:32 pm
ORD
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OGG
15h 42m
2 stops
$476Delta
Thu, Apr 16 - Mon, Apr 20
Alaska Airlines Logo
11:02 pm - 11:59 pm
OGG
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ORD
19h 57m
1 stop
Alaska Airlines Logo
4:10 pm - 10:02 pm
ORD
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OGG
34h 52m
1 stop
$492Alaska Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$185
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Kahului to Chicago O'Hare Airport

FAQs for booking Maui to Chicago O'Hare Airport flights

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

    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 Maui to Chicago O'Hare Airport.

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

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

    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 O'Hare Airport with an airline and back to Maui with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Chicago O'Hare Airport?

    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 O'Hare Airport from Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Maui to O'Hare Intl

 
Need help choosing which airline to fly with from Maui to O'Hare Intl? 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 12025 reviews
7.1Food
7.0Entertainment
7.8Comfort
8.1Boarding
8.5Crew
Airline reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

6.0 GoodAnonymous, Feb 2026
BNA - ORD
Read more Alaska Airlines reviews

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

I was in economy class and there was plenty of leg room. New interior which was nice and they served various kinds of chips and sodas on the red eye. You couldn't get a bottle of water but they instead served it in a medium paper cup from a reinforced structured paper container, environmental friendly.

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!

Horrible food and crew. Crew were laughing and talking loud while people were trying to sleep

I liked the Starlink WiFi but didn't like how they said they were the only airline to offer a free meal and it turns out to be just a standalone sandwich and then charge for snacks to go with it. Rather have the free snacks like Southwest, but have the option to purchase a decent meal for a 5+ hour flight.

Delayed and cancelled flights were hard and very stressful, both ways!

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

Previously flown Hawaiian Airlines on similar routes, I found Alaska Airlines to be noticeably more comfortable. The seats on Alaska Airlines provided better support and cushioning, which made a significant difference on the long flight to the islands. When you’re spending 5-6 hours in the air, seat comfort really matters, and Alaska Airlines delivered where it counts. After comparing both carriers, I’ve decided to book with Alaska Airlines for all my future Hawaii trips. The superior seat comfort alone makes it worth choosing Alaska over Hawaiian Airlines. If you’re planning a trip to Hawaii and prioritizing comfort, I’d recommend giving Alaska Airlines a try. You won’t be disappointed. Highly recommended for Hawaii travel!

The crew was EXTREMELY helpful And sweet and the flight was smooth!

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.

Flying with Hawaiian Airlines is a treat! They have the best crew, food and drinks! I’ve always enjoyed flying with Hawaiian Airlines and will continue to use them!

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hammond
Hoffman Estates
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Lisle
Elmhurst
Valparaiso

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