ORD

$170 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 5/6. 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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Everything you should know

Cheapest round-trip
$342
Alaska Airlines
Wed 4/29Mon 5/4
OGG - ORD • 1 stop
Cheapest non-stop
$815
United Airlines
Mon 3/23Mon 3/30
OGG - ORD • Non-stop
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Flight Deals
Useful Info
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 29 - Mon, May 4
Alaska Airlines Logo
10:41 pm - 2:41 pm
OGG
-
ORD
11h 00m1 stop
Alaska Airlines Logo
7:59 pm - 8:52 pm
ORD
-
OGG
29h 53m1 stop
$342Alaska Airlines
Wed, Apr 29 - Mon, May 4
Delta Logo
8:05 pm - 12:25 pm
OGG
-
ORD
11h 20m1 stop
Delta Logo
7:20 am - 7:31 pm
ORD
-
OGG
17h 11m2 stops
$364Delta
Wed, Apr 29 - Mon, May 4
Delta Logo
12:40 pm - 8:38 am
OGG
-
ORD
14h 58m2 stops
Delta Logo
7:20 am - 7:31 pm
ORD
-
OGG
17h 11m2 stops
$369Delta
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
11:59 pm - 11:37 pm
OGG
-
ORD
19h 38m1 stop
Multiple Airlines Logo
9:00 am - 6:51 am
ORD
-
OGG
25h 51m2 stops
$403Multiple Airlines
Mon, Mar 23 - Mon, Mar 30
Multiple Airlines Logo
3:10 pm - 4:49 am
OGG
-
ORD
32h 39m1 stop
Multiple Airlines Logo
4:05 pm - 11:17 am
ORD
-
OGG
48h 12m2 stops
$405Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Alaska Airlines Logo
2:03 pm - 11:37 pm
OGG
-
ORD
29h 34m1 stop
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
$409Alaska Airlines
Mon, Mar 23 - Mon, Mar 30
Multiple Airlines Logo
3:10 pm - 4:49 am
OGG
-
ORD
32h 39m1 stop
Multiple Airlines Logo
7:49 pm - 11:17 am
ORD
-
OGG
20h 28m1 stop
$410Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Alaska Airlines Logo
11:00 pm - 11:50 pm
OGG
-
ORD
20h 50m1 stop
Alaska Airlines Logo
2:06 pm - 10:00 pm
ORD
-
OGG
11h 54m1 stop
$417Alaska Airlines
Thu, Jan 29 - Sun, Feb 1
Alaska Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
Alaska Airlines Logo
2:06 pm - 10:00 pm
ORD
-
OGG
11h 54m1 stop
$419Alaska Airlines
Wed, Feb 11 - Sat, Feb 14
Delta Logo
10:00 pm - 1:22 pm
OGG
-
ORD
11h 22m1 stop
Delta Logo
7:15 am - 7:15 pm
ORD
-
OGG
16h 00m1 stop
$439Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$170
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 2% 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 11672 reviews
7.0Entertainment
8.5Crew
7.1Food
8.1Boarding
7.8Comfort
Airline reviews

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.

10.0 ExcellentAnonymous, Dec 2025
SAN - ORD
Read more Alaska Airlines reviews

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!

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.

I know airlines have to save money, but a little more legroom would be nice. I’m a small person and I just felt cramped after a few hours. However, I loved everything else! Free Alaska Airlines wifi, free movies, yummy snacks, and the crew was so helpful and accommodating!

I love the flight ✈️ Hawaiian Airlines. All stuffs are fantastic members ♡ sweet hearts and families warm welcome 🙏 I have milage of Hawaiian Airlines members so get points .also I booked kayak agent got cheap price ! I satisfied flight with Hawaiian Airlines ♡ thank you

Good, but because I fly internationally I found the food and service lousy compared to European standards. You should include a regular small mean (and not a lousy sandwich) and ear phones. People who travel from Europe are not aware of limited services.

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!

Amazing all female crew, including the pilot. Great flight attendants and smooth trip. Food was good. Boarding the plane from back to front would have made things significantly smoother. Took forever to wait for people to clear the alley. A little extra leg room would be nice also. Please thank your flight crew!

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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
Hoffman Estates
Hammond
Willowbrook
Portage
South Holland
Delavan
Northbrook
Pleasant Prairie
Lansing
Elmhurst
Lisle
Valparaiso

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