Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

$179 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 5/23. 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 6/1
Sat 6/8

Search hundreds of travel sites at once for deals on flights to Chicago

In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Good to know

Low season

January

High season

October

Cheapest flight

$179
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 22% 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 10861 reviews
8.0Entertainment
7.4Food
8.6Crew
8.2Boarding
7.9Comfort
Airline reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

8.0 ExcellentAnonymous, May 2024ATL - ATW
Read more about Delta reviews

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

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

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.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Maui to Chicago

Recent round-trip flight deals

5/24Fri
1 stopAlaska Airlines
32h 44mOGG-ORD
5/30Thu
1 stopAlaska Airlines
19h 42mORD-OGG
$475
8/18Sun
2 stopsDelta
20h 17mOGG-ORD
9/10Tue
1 stopDelta
27h 29mORD-OGG
$488
8/18Sun
2 stopsDelta
20h 17mOGG-ORD
9/9Mon
1 stopDelta
14h 53mORD-OGG
$518
8/18Sun
2 stopsDelta
20h 17mOGG-ORD
9/4Wed
1 stopDelta
14h 44mORD-OGG
$520
8/18Sun
2 stopsDelta
20h 17mOGG-ORD
9/5Thu
2 stopsDelta
19h 10mORD-OGG
$521
8/18Sun
2 stopsDelta
20h 17mOGG-ORD
9/7Sat
2 stopsDelta
24h 17mORD-OGG
$523
5/15Wed
1 stopAmerican Airlines
12h 55mOGG-ORD
5/18Sat
1 stopAmerican Airlines
10h 46mORD-OGG
$547
8/21Wed
1 stopAmerican Airlines
10h 51mOGG-ORD
8/28Wed
2 stopsAmerican Airlines
13h 39mORD-OGG
$553
6/2Sun
1 stopUnited Airlines
11h 52mOGG-ORD
6/6Thu
1 stopUnited Airlines
13h 57mORD-OGG
$564
5/24Fri
1 stopUnited Airlines
25h 55mOGG-ORD
5/30Thu
2 stopsUnited Airlines
18h 41mORD-OGG
$627

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/23Thu
1 stopAmerican Airlines
11h 44mOGG-ORD
$179
5/23Thu
2 stopsDelta
16h 41mOGG-ORD
$184
6/6Thu
1 stopDelta
10h 24mOGG-ORD
$211
5/18Sat
1 stopAlaska Airlines
33h 29mOGG-ORD
$264
5/20Mon
1 stopAmerican Airlines
12h 57mOGG-ORD
$266
5/18Sat
1 stopAlaska Airlines
33h 29mOGG-ORD
$272
6/6Thu
2 stopsAlaska Airlines
33h 14mOGG-ORD
$278
5/30Thu
1 stopAlaska Airlines
33h 29mOGG-ORD
$281
7/3Wed
1 stopUnited Airlines
21h 40mOGG-ORD
$368
5/29Wed
1 stopUnited Airlines
13h 35mOGG-ORD
$379

Search by stops

Search by airline

Search by price

Last minute flights from Maui to Chicago

Last minute flight, train and bus deals

5/7Tue
multi-stopAlaska Airlines
26h 56mOGG-ORD
5/10Fri
multi-stopAlaska Airlines
34h 38mORD-OGG
$547
5/5Sun
multi-stopAmerican Airlines
13h 35mOGG-ORD
5/14Tue
multi-stopAmerican Airlines
13h 10mORD-OGG
$590
5/3Fri
multi-stopAlaska Airlines
26h 56mOGG-ORD
5/6Mon
multi-stopAlaska Airlines
13h 47mORD-OGG
$597
5/7Tue
multi-stopUnited Airlines
11h 52mOGG-ORD
5/10Fri
multi-stopUnited Airlines
14h 52mORD-OGG
$727
5/5Sun
multi-stopUnited Airlines
11h 06mOGG-ORD
5/14Tue
multi-stopUnited Airlines
20h 57mORD-OGG
$739
5/3Fri
multi-stopUnited Airlines
10h 50mOGG-ORD
5/6Mon
multi-stopUnited Airlines
14h 52mORD-OGG
$809
5/5Sun
multi-stopUnited Airlines
13h 30mOGG-ORD
5/14Tue
multi-stopUnited Airlines
23h 12mORD-OGG
$842
5/3Fri
multi-stopDelta
14h 10mOGG-ORD
5/6Mon
multi-stopDelta
15h 37mORD-OGG
$913
5/3Fri
multi-stopDelta
18h 46mOGG-MDW
5/6Mon
multi-stopDelta
16h 47mMDW-OGG
$1,027

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Maui

Cabin classes:

$274
$293
$219
$38