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$247 Find Cheap Flights from Maui to Chicago O'Hare Airport - Compare and Save

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Cheap Flights from Maui to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Maui to O'Hare Intl

Thu, Oct 8 - Wed, Oct 14
Alaska Airlines Logo
10:59 pm - 1:25 pmOGG  Kahului-ORD Chicago O'Hare Intl
33h 26m1 stop San Diego
Alaska Airlines Logo
2:21 pm - 9:59 pmORD  Chicago O'Hare Intl-OGG Kahului
12h 38m1 stop San Diego
$515Alaska Airlines
Tue, Oct 20 - Tue, Nov 3
Alaska Airlines Logo
10:59 pm - 1:25 pmOGG  Kahului-ORD Chicago O'Hare Intl
33h 26m1 stop San Diego
Alaska Airlines Logo
2:15 pm - 9:49 pmORD  Chicago O'Hare Intl-OGG Kahului
11h 34m1 stop San Diego
$516Alaska Airlines
Tue, Oct 20 - Tue, Nov 3
Multiple Airlines Logo
10:59 pm - 6:53 pmOGG  Kahului-ORD Chicago O'Hare Intl
14h 54m1 stop San Diego
Multiple Airlines Logo
2:15 pm - 10:27 amORD  Chicago O'Hare Intl-OGG Kahului
24h 12m2 stops San Diego San Francisco
$529Multiple Airlines
Wed, Oct 28 - Mon, Nov 2
Alaska Airlines Logo
10:59 pm - 11:59 pmOGG  Kahului-ORD Chicago O'Hare Intl
20h 00m1 stop San Diego
Alaska Airlines Logo
7:20 am - 9:49 pmORD  Chicago O'Hare Intl-OGG Kahului
18h 29m1 stop San Diego
$534Alaska Airlines
Wed, Oct 28 - Mon, Nov 2
Multiple Airlines Logo
10:59 pm - 6:53 pmOGG  Kahului-ORD Chicago O'Hare Intl
14h 54m1 stop San Diego
Multiple Airlines Logo
2:15 pm - 10:27 amORD  Chicago O'Hare Intl-OGG Kahului
24h 12m2 stops San Diego San Francisco
$558Multiple Airlines
Mon, Nov 9 - Wed, Nov 11
Multiple Airlines Logo
1:28 pm - 6:59 pmOGG  Kahului-ORD Chicago O'Hare Intl
25h 31m1 stop San Diego
Multiple Airlines Logo
7:20 am - 6:16 pmORD  Chicago O'Hare Intl-OGG Kahului
14h 56m2 stops San Diego Honolulu
$564Multiple Airlines
Sat, Nov 21 - Sat, Nov 28
United Airlines Logo
5:10 pm - 5:02 amOGG  Kahului-ORD Chicago O'Hare Intl
7h 52mnonstop
United Airlines Logo
7:00 am - 4:37 pmORD  Chicago O'Hare Intl-OGG Kahului
13h 37m1 stop Denver Intl
$984United Airlines
Sat, Oct 10 - Sat, Oct 17
United Airlines Logo
1:05 pm - 4:45 amOGG  Kahului-ORD Chicago O'Hare Intl
10h 40m1 stop Los Angeles
United Airlines Logo
9:20 am - 1:16 pmORD  Chicago O'Hare Intl-OGG Kahului
8h 56mnonstop
$1,024United Airlines
Sat, Oct 10 - Sat, Oct 17
United Airlines Logo
4:10 pm - 5:00 amOGG  Kahului-ORD Chicago O'Hare Intl
7h 50mnonstop
United Airlines Logo
9:20 am - 1:16 pmORD  Chicago O'Hare Intl-OGG Kahului
8h 56mnonstop
$1,130United Airlines
Wed, Dec 16 - Wed, Dec 23
American Airlines Logo
7:45 pm - 11:00 amOGG  Kahului-ORD Chicago O'Hare Intl
11h 15m1 stop Dallas/Fort Worth
American Airlines Logo
12:00 pm - 5:04 pmORD  Chicago O'Hare Intl-OGG Kahului
9h 04mnonstop
$1,221American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$247
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 14% 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.
7.9
Alaska AirlinesOverall score based on 12866 reviews
7.8Comfort
7.0Food
8.1Boarding
7.0Entertainment
8.5Crew
Airline reviews

Potatoes were not cooked in the pork potato meal. Flight attendants were great in first class.

10.0 ExcellentJane, Aug 2026
Read more Alaska Airlines reviews

Potatoes were not cooked in the pork potato meal. Flight attendants were great in first class.

I paid extra to choose my seat. I chose a window seat. I don’t know if it was a disconnect between KAYAK or the airline but when we got to the airport, the seat was changed to a middle seat. Didn’t notice it til at the gate. I called wanted a refund and was told that I didn’t choose the seat even though on my KAYAK reservation it showed seat 12 A. So I paid extra for seat selection, but didn’t get it. And also did not get a refund. I specifically pay the extra for a seat selection. I normally am very happy with Alaska Airlines. They are usually in my top three of choices.

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

Worst travel day of my life. First bumped from our 7am flight—that we booked to ensure enough time to get to Chicago and get ready to go to a concert. Ended up on a flight 5hours later only to arrive in Chicago and spend 2 hours sitting in the tarmac. Missed the concert ($650 in tickets) and was too late to cancel the hotel ($500). I did receive a $200 voucher for the next Alaska ticket—soooo generous 👎. Would LOVE if Alaska reimbursed the $1000+that I am out!

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

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.

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

Traveling to a place near O'Hare Intl?

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

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