$231 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 11/17. 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

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Cheap Flights from Maui to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maui to Chicago 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 Chicago

Thu, Aug 14 - Tue, Sep 2
Alaska Airlines Logo
9:39 pm - 11:39 pmOGG-ORD
21h 00m1 stop
Alaska Airlines Logo
6:20 am - 3:58 pmORD-OGG
14h 38m1 stop
$498Alaska Airlines
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Thu, Aug 14 - Tue, Sep 2
Alaska Airlines Logo
10:34 pm - 11:39 pmOGG-ORD
20h 05m2 stops
Alaska Airlines Logo
6:20 am - 3:58 pmORD-OGG
14h 38m1 stop
$503Alaska Airlines
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Tue, Jul 29 - Thu, Aug 7
Hawaiian Airlines Logo
12:20 pm - 5:40 amOGG-ORD
12h 20m1 stop
Hawaiian Airlines Logo
6:00 am - 1:40 pmORD-OGG
12h 40m1 stop
$678Hawaiian Airlines
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Wed, Jul 2 - Tue, Jul 15
Southwest Logo
6:00 am - 11:40 pmOGG-ORD
12h 40m2 stops
Southwest Logo
7:00 am - 5:05 pmORD-OGG
15h 05m2 stops
$759Southwest
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Thu, Jul 17 - Sun, Jul 20
Southwest Logo
8:30 pm - 6:05 pmOGG-MDW
16h 35m1 stop
Southwest Logo
8:05 am - 4:30 pmMDW-OGG
13h 25m1 stop
$773Southwest
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Thu, Jul 10 - Thu, Jul 17
United Airlines Logo
12:10 pm - 7:30 amOGG-ORD
14h 20m2 stops
United Airlines Logo
7:20 am - 4:22 pmORD-OGG
14h 02m1 stop
$865United Airlines
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Wed, Jul 9 - Thu, Jul 17
United Airlines Logo
12:10 pm - 7:30 amOGG-ORD
14h 20m2 stops
United Airlines Logo
7:20 am - 4:22 pmORD-OGG
14h 02m1 stop
$890United Airlines
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Mon, Jul 14 - Thu, Jul 24
American Airlines Logo
9:38 pm - 2:03 pmOGG-ORD
11h 25m1 stop
American Airlines Logo
6:13 am - 11:53 amORD-OGG
10h 40m1 stop
$957American Airlines
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Wed, Jul 16 - Tue, Jul 22
American Airlines Logo
9:38 pm - 2:03 pmOGG-ORD
11h 25m1 stop
American Airlines Logo
6:13 am - 11:53 amORD-OGG
10h 40m1 stop
$971American Airlines
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Sat, Jul 5 - Sat, Jul 12
Hawaiian Airlines Logo
11:15 am - 5:40 amOGG-ORD
13h 25m1 stop
Hawaiian Airlines Logo
1:03 pm - 9:34 pmORD-OGG
13h 31m1 stop
$1,026Hawaiian Airlines
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Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$231
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Kahului to Chicago Midway 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.

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
Alaska AirlinesOverall score based on 10000 reviews
7.1Entertainment
7.8Comfort
7.1Food
8.1Boarding
8.5Crew
Airline reviews

Really good except my daughter's tv broke during the flight so she could watch tv

10.0 ExcellentAnonymous, Jun 2025HNL - JFK
Read more Alaska Airlines reviews

Really good except my daughter's tv broke during the flight so she could watch tv

I would've liked to have the seat tablets like before to view movies, with long travels not everyone carries tablets to view movies. And phones are not worth it because screens to small.

Horrible! No blanket or pillow available! We had bulkhead seats but the seats were worn out and no cushion old. No meal or even a sandwich for our 5 hour flight just a little bag of pretzels. Crabby attendant female with long brown hair. We will not book Alaska Airlines again

Terrible check in experience, and they ended up losing our bag.

they didn't fix a plane and we were delayed travelling an extra 12 hours.

Well, the baggage porter on Maui told my mom that our carry on luggage was overweight and if she gave him a 50 dollar tip he would let it go through. She tipped him and he tells us that he needs my Alaska airlines cc to waive the extra baggage charge. Find out later that since my original reservation was not under my name using a Hawaiian airlines CC, I would have to pay for the luggage anyway. I told them I had to end up paying for my daughters ticket when you all said because she turned two using my Alaska Airlines cc, now they need to charge me for her seat/flight, but you guys didn't care and i ended up paying for the bags and my mom paid the porter 50 dollars extra for nothing .. It was a crappy experience. First it was a multi trip. PDX-HNL then HNL-OGG then OGG to PDX. All bought under one ticket. My daugher turned two during the flight from HNL-OGG, but when I bought the ticket and at the PDX airport they said since i bought the ticket before she was two, everything is fine. come to find out no, I had to pay her ticket HNL-OGG and again OGG to PDX. you guys scammed me. You should say it on your website and make sure people know that during flights if the child turns two they have to pay for their seat. If i knew that from the very beginning i would have bought her ticket and it would have been LESS than paying TWICE for her flight! and you scammed my mother with you porter who told her to pay him 50 dollars and he would take care of the extra luggage weight.

Horrible! Cancelled our flight after almost 3hr delay. 5 1/2hrs of our day wasted in an airport, only to have to figure out what hotel we need to stay in, transportation and contacting our jobs so they know we will miss work. Rebooked us for a next day flight and didn’t keep our premium seating from our original flight. The worse!!!

Express the need to arrive at the airport more than 2 hours ahead of BOARDING TIME due to super slow security lines at the Lihue airport. 4 ppl in a party of 9 nearly missed the boarding.

Way too warm for that length of flight!! If the pretzel bag gets any smaller, there won't even be any pretzels to eat!! Crew didn't talk. $99 just for an aisle seat is ludicrous!! Probably won't fly Alaska again.

Our big luggage never made it to Boston. Very crucial to get it ASAP as heart medication is in there.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maui

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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