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

$175 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 9/18. 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
sáb. 7/13
sáb. 7/20

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

In the last 7 days travelers have searched 44,216,777 times on KAYAK, and here is why:

Save 21% 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

March

High season

October

Cheapest flight

$175
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 9% 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, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights

Nonstop returns

Chicago to Maui

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 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 10000 reviews
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
7.9Comfort
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

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

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

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.

Book cheap flights from Maui to Chicago

Recent round-trip flight deals

8/13mar.
1 stopAlaska Airlines
26h 01mOGG-ORD
8/20mar.
1 stopAlaska Airlines
20h 07mORD-OGG
$349
8/13mar.
1 stopAlaska Airlines
26h 01mOGG-ORD
8/20mar.
2 stopsAlaska Airlines
32h 27mORD-OGG
$361
8/13mar.
2 stopsAlaska Airlines
26h 36mOGG-ORD
8/20mar.
2 stopsAlaska Airlines
32h 27mORD-OGG
$406
8/30vie.
1 stopAmerican Airlines
19h 20mOGG-ORD
9/3mar.
1 stopAmerican Airlines
11h 02mORD-OGG
$408
7/20sáb.
1 stopDelta
10h 10mOGG-ORD
7/27sáb.
1 stopDelta
15h 03mORD-OGG
$480
8/30vie.
2 stopsAlaska Airlines
20h 18mOGG-ORD
9/3mar.
1 stopAlaska Airlines
19h 47mORD-OGG
$552
8/30vie.
2 stopsDelta
15h 32mOGG-ORD
9/3mar.
2 stopsDelta
15h 35mORD-OGG
$649
7/20sáb.
nonstopUnited Airlines
7h 54mOGG-ORD
7/27sáb.
1 stopUnited Airlines
11h 30mORD-OGG
$751
6/23dom.
1 stopAmerican Airlines
9h 45mOGG-ORD
8/3sáb.
2 stopsAmerican Airlines
13h 48mORD-OGG
$924
7/20sáb.
nonstopUnited Airlines
7h 54mOGG-ORD
7/27sáb.
nonstopUnited Airlines
8h 51mORD-OGG
$971

Search by stops

Search by airline

Search by price

Recent one-way flight deals

9/18mié.
1 stopAmerican Airlines
10h 28mOGG-ORD
$175
10/29mar.
1 stopAmerican Airlines
11h 31mOGG-ORD
$176
10/28lun.
1 stopDelta
33h 33mOGG-ORD
$188
10/28lun.
1 stopAlaska Airlines
20h 58mOGG-ORD
$192
10/28lun.
2 stops
26h 24mOGG-ORD
$198
9/18mié.
2 stopsDelta
13h 46mOGG-ORD
$201
10/28lun.
3 stops
27h 31mOGG-ORD
$207
7/4jue.
1 stopAlaska Airlines
33h 13mOGG-ORD
$228
7/13sáb.
1 stopUnited Airlines
36h 35mOGG-ORD
$393
8/8jue.
2 stopsUnited Airlines
20h 54mOGG-ORD
$437

Search by stops

Search by airline

Search by price

Last minute flights from Maui to Chicago

Last minute flight, train and bus deals

6/14vie.
multi-stopAlaska Airlines
11h 48mOGG-ORD
6/16dom.
multi-stopAlaska Airlines
25h 47mORD-OGG
$796
6/14vie.
multi-stop
18h 53mOGG-ORD
6/16dom.
multi-stop
14h 07mORD-OGG
$875
6/18mar.
multi-stopDelta
16h 10mOGG-ORD
6/25mar.
multi-stopDelta
14h 57mORD-OGG
$908
6/14vie.
multi-stopAmerican Airlines
13h 14mOGG-ORD
6/16dom.
multi-stopAmerican Airlines
13h 53mORD-OGG
$942
6/18mar.
multi-stopAmerican Airlines
10h 40mOGG-ORD
6/25mar.
multi-stopAmerican Airlines
10h 52mORD-OGG
$958
6/18mar.
multi-stopDelta
15h 32mOGG-ORD
6/25mar.
multi-stopDelta
18h 29mORD-OGG
$1,052

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Maui

Cabin classes:

$360
$232
$231
$44