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$171 Find cheap flights from Maui to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 10/31. 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
0 bags
Sat 6/22
Sat 6/29

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Good to know

Low season

March

High season

October

Cheapest flight

$171
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Kahului to Chicago O'Hare Airport

FAQs for booking flights from Maui to Chicago

  • How does KAYAK find such low prices on flights from Maui to Chicago?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 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?

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

See more FAQs

Prefer to fly non-stop from Maui to Chicago?

Find which airlines fly direct from Maui to Chicago, which days they fly and book direct flights.

Nonstop departures

Maui to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Maui

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 3 airlines serving from Maui to Chicago

 
Need help choosing which airline to fly with from Maui to Chicago? 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
DeltaOverall score based on 10561 reviews
8.0Entertainment
7.9Comfort
8.6Crew
7.4Food
8.2Boarding
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Maui to Chicago

Recent round-trip flight deals

7/2Tue
1 stopUnited Airlines
12h 45mOGG-ORD
7/10Wed
1 stopUnited Airlines
14h 03mORD-OGG
$527
7/2Tue
1 stopDelta
14h 22mOGG-ORD
7/10Wed
1 stopDelta
15h 03mORD-OGG
$542
7/18Thu
1 stopUnited Airlines
10h 05mOGG-ORD
7/29Mon
1 stopUnited Airlines
14h 03mORD-OGG
$558
6/18Tue
1 stopUnited Airlines
11h 00mOGG-ORD
8/2Fri
1 stopUnited Airlines
12h 33mORD-OGG
$563
7/18Thu
2 stopsAlaska Airlines
27h 41mOGG-ORD
7/29Mon
2 stopsAlaska Airlines
19h 04mORD-OGG
$608
7/18Thu
2 stopsAlaska Airlines
27h 41mOGG-ORD
7/29Mon
1 stopAlaska Airlines
31h 52mORD-OGG
$610
6/18Tue
1 stopAlaska Airlines
27h 57mOGG-ORD
8/2Fri
2 stopsAlaska Airlines
17h 39mORD-OGG
$620
7/2Tue
1 stopUnited Airlines
12h 45mOGG-ORD
7/10Wed
2 stopsUnited Airlines
13h 22mORD-OGG
$633
6/24Mon
1 stopAlaska Airlines
26h 01mOGG-ORD
7/2Tue
1 stopAlaska Airlines
28h 17mORD-OGG
$643
7/2Tue
1 stopDelta
14h 22mOGG-ORD
7/10Wed
2 stopsDelta
18h 30mORD-OGG
$730

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Recent one-way flight deals

10/31Thu
1 stopDelta
15h 18mOGG-ORD
$171
5/29Wed
1 stopAlaska Airlines
33h 29mOGG-ORD
$226
8/22Thu
2 stopsDelta
16h 24mOGG-ORD
$228
8/22Thu
1 stopAmerican Airlines
17h 46mOGG-ORD
$229
5/28Tue
1 stopAmerican Airlines
11h 15mOGG-ORD
$231
8/12Mon
2 stopsDelta
17h 00mOGG-ORD
$236
7/16Tue
2 stopsAlaska Airlines
33h 33mOGG-ORD
$260
8/6Tue
1 stopUnited Airlines
17h 37mOGG-ORD
$318
8/11Sun
1 stopUnited Airlines
27h 25mOGG-ORD
$353
8/11Sun
3 stopsWestJet
34h 44mOGG-MDW
$902

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Last minute flights from Maui to Chicago

Last minute flight, train and bus deals

5/24Fri
multi-stopAlaska Airlines
33h 29mOGG-ORD
5/30Thu
multi-stopAlaska Airlines
23h 31mORD-OGG
$450
5/24Fri
multi-stopAmerican Airlines
12h 57mOGG-ORD
5/30Thu
multi-stopAmerican Airlines
10h 46mORD-OGG
$462
5/24Fri
multi-stopDelta
13h 59mOGG-ORD
5/30Thu
multi-stopDelta
14h 14mORD-OGG
$472
5/24Fri
multi-stopDelta
13h 59mOGG-ORD
5/30Thu
multi-stopDelta
15h 59mORD-OGG
$479
5/24Fri
multi-stopDelta
13h 59mOGG-ORD
5/31Fri
multi-stopDelta
15h 52mORD-OGG
$551
5/24Fri
multi-stopDelta
14h 05mOGG-MDW
5/31Fri
multi-stopDelta
16h 09mMDW-OGG
$634
5/24Fri
multi-stopAmerican Airlines
12h 57mOGG-ORD
5/27Mon
multi-stopAmerican Airlines
14h 27mORD-OGG
$637
5/24Fri
multi-stopDelta
13h 59mOGG-ORD
5/27Mon
multi-stopDelta
15h 41mORD-OGG
$687
5/24Fri
multi-stopUnited Airlines
11h 00mOGG-ORD
5/31Fri
multi-stopUnited Airlines
21h 03mORD-OGG
$697
5/24Fri
multi-stopDelta
14h 05mOGG-MDW
5/27Mon
multi-stopDelta
13h 57mMDW-OGG
$952

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Flights to Chicago

Return flight deals:

Chicago - Maui

Cabin classes:

$340
$307
$245
$40