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Find cheap flights from Chicago to Maui from $226

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Maui departing on 5/13. 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
Thu 5/16
Thu 5/23

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Best Maui Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Kahului
Kahului1 stop$358

Good to know

Low season

September

High season

December

Cheapest flight

$226
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago O'Hare Airport to Kahului

FAQs - booking Maui flights

  • Is there a nursing room at the O'Hare International Airport (ORD)?

    If you're a mother traveling with toddlers, you can breastfeed or nurse them in the designated mother's rooms at O'Hare International Airport in every terminal. The rooms are ADA-compliant and have soft lighting, electrical outlets, comfy seats, a diaper-changing table, and a sink. Additionally, you can use the lactation pods at Gate B7 in Concourse B of Terminal 1 and Gate C11 in Concourse C of Terminal 1.

  • Are there hotels near Kahului Airport (OGG) that offer complimentary airport shuttle services?

    Several hotels in Maui offer complimentary shuttle service to and from the airport, which is convenient if you're arriving late or leaving early. Some of the airports are located within a walking distance from the airport. You can also check into Premier Lounge by Hawaiian Airlines located at Airside on Gate 17 for a rest and take fresh foods and drinks before embarking on your journey.

  • Are there direct flights from Chicago's Midway Airport (MDW) to Maui?

    There is not a single airline that flies nonstop from Chicago's Midway Airport to Maui. However, several airlines now provide nonstop service to a variety of destinations. While Delta offers a layover in Atlanta (ATL), Southwest offers layovers in Las Vegas (LAS) and Oakland (OAK).

  • Is there a family lounge at O'Hare International Airport (ORD)?

    The Family Lounge at O'Hare International Airport is a special area for families with kids, located in Terminal 2 at Gate F1 after passengers have passed through security. You can relax in one of the many brightly colored chairs, charge your electronic devices, and even leave your baby's stroller in the stroller parking area. Artists, comic artists, and others provide live performances at various periods of the year, with the holiday season drawing the most crowds.  

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

    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 Chicago to Maui.

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

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

    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 Maui with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Maui?

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

See more FAQs

Top tips for finding cheap flights to Maui

  • If you need a place to relax before boarding a flight to Maui from Chicago's O'Hare International Airport (ORD), you can stop by one of the United Airlines lounges, including the United Club lounge, which is in Terminal 1 near Gate B6 or Terminal 1 at Gate B18 for a round of refreshments.
  • You can schedule a flight to Maui's Hana Airport (HNM) at any aiport in Chicago. United Airlines and Southern Airways Express provide multi-stop itineraries that include a stop at Kahului Airport (OGG) before continuing to Hana Airport, so it should be easy to find a route that works for you.
  • If you hop into a plane from Chicago's O'Hare International Airport, you may fly nonstop to Maui from Boston (BOS) on United Airlines without stopping anywhere between.
  • You can head downtown from Kahului Airport (OGG) by taking the Airport Shuttle or a taxi. Taxis are the quickest way to get downtown, taking only around 7 minutes to travel the two miles there under perfect traffic circumstances.
  • Those flying from Chicago's Midway International Airport (MDW) to Maui with their service animals can spend quality time together at the airport's designated pet areas. The outdoor service area can be found towards the southern end of the Lower Level terminal road. The indoor service area is situated in Concourse A, next to Gate A4A. A bench and waste-disposal bags are available in the service area.
See more tips

Top 4 airlines serving from Chicago to Maui

 
Need help choosing which airline to fly with from Chicago to Maui? 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.
8.1
Alaska AirlinesOverall score based on 9054 reviews
7.3food
8.6crew
7.9comfort
8.2boarding
7.3entertainment
Airline reviews

I would have rated the entire experience much better were it not for two things: 1. There was inconsistency between what we were told once on the plane vs. the answer I received to the question about "spreading out" from our assigned seats because the flight was sparsely populated, and the entire row we were in was empty but for us. I asked about one of us moving over one seat to make more room for us; before getting on the plane, I was told we could, which seemed like a sensible answer. Once on the plane, it was announced that we needed to stay in our assigned seats despite all of the empty space in our row, which seemed unneccessarily restrictive. 2. To add to the discomfort, we sat on the tarmac once the plane landed in Burbank for over half an hour waiting for a gate to become available. During that time we had to remain seated and buckled in, which was becoming more difficult as time dragged on, especially for my wife. If all of this was due to regulations, that may mitigate the sense of "needless" restriction somewhat, but it points to a need to make regulations less restrictive where it is not appropriate for the current conditions. The crew was not "nasty" about the restrictions, so I do not resent their actions, but it certainly would have been a much more pleasant flight if we had a few more options when it comes to comfort.

6.0 GoodBob, Apr 2024PDX - BUR
Read more about Alaska Airlines reviews

I would have rated the entire experience much better were it not for two things: 1. There was inconsistency between what we were told once on the plane vs. the answer I received to the question about "spreading out" from our assigned seats because the flight was sparsely populated, and the entire row we were in was empty but for us. I asked about one of us moving over one seat to make more room for us; before getting on the plane, I was told we could, which seemed like a sensible answer. Once on the plane, it was announced that we needed to stay in our assigned seats despite all of the empty space in our row, which seemed unneccessarily restrictive. 2. To add to the discomfort, we sat on the tarmac once the plane landed in Burbank for over half an hour waiting for a gate to become available. During that time we had to remain seated and buckled in, which was becoming more difficult as time dragged on, especially for my wife. If all of this was due to regulations, that may mitigate the sense of "needless" restriction somewhat, but it points to a need to make regulations less restrictive where it is not appropriate for the current conditions. The crew was not "nasty" about the restrictions, so I do not resent their actions, but it certainly would have been a much more pleasant flight if we had a few more options when it comes to comfort.

Red eye flight, so not expecting any extras, but the boarding and trip was smooth. Thx Alaska.

It was the worst experience because they delayed the flight by 2 and half hours. We were supposed to depart by 3:41 but they did the depart by 6 pm. It was so boring!!

The cabin temperature was very warm. Flight attendant did not help when my 3 YO needed to go to the bathroom and it was close to landing time. She knocked and opened the door. I would appreciate more empathy towards the situation.

I’m a first time mom and traveled with my 18mo old boy and it was not a great experience with the flight attendants. They were not friendly or helpful at all. It’s hard enough traveling with a toddler and have people be rude and unkind does not help.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

Window seat and a packed plane. A very uncomfortable flight.

My flights went about as good as they could be. I’ll always take Alaska when possible.

The pilot and crew did everything they possibly could on an airline flight to make everyone comfortable and fed and informed and both flights to and from were flawless and safe and I couldn't imagine flying on another airline when I visit the Hawaiian islands

Flight crew was above average personal. I could see that they loved their jobs!

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

Boarding was great. The flight landed early. It took the crew over an hour and a half to bring out drinks. I paid to upgrade my seat to Comfort+ only to be near a crying/screaming baby who was seldom quiet. Noise-cancelling earbuds didn’t even help. Waste of money to upgrade.

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

On 2 different flights the wifi was horrible and there was no drink or snack service.

Wifi wasn’t working well so we couldn't view any media.

Flight was late. Club was full. Experience is exactly what I expected.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Nothing bad to say about the actual crew or airline. It was nice to have a complimentary FULL can of soda, as well as a snack. Blankets and earbuds were also provided at no cost for this red eye flight. I especially appreciated the free WiFi and movie selection with the Bluetooth option. It helped the flight pass more quickly. No matter who you fly, boarding and disembarking are always SUCH a pain. As I mentioned, this is on the passengers and not the crew!!

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Maui

Recent round-trip flight deals

5/7Tue
1 stopAmerican Airlines
13h 10mORD-OGG
5/14Tue
1 stopAmerican Airlines
11h 17mOGG-ORD
$358
5/7Tue
2 stopsDelta
17h 29mORD-OGG
5/14Tue
1 stopDelta
10h 44mOGG-ORD
$411
4/28Sun
2 stopsDelta
17h 07mORD-OGG
5/7Tue
1 stopDelta
10h 44mOGG-ORD
$436
9/17Tue
1 stopDelta
14h 53mORD-OGG
10/1Tue
1 stopDelta
15h 18mOGG-ORD
$454
5/15Wed
1 stop
28h 01mMDW-OGG
5/19Sun
1 stop
22h 07mOGG-MDW
$457
5/15Wed
1 stop
28h 01mMDW-OGG
5/19Sun
2 stops
17h 59mOGG-MDW
$482
5/10Fri
1 stopUnited Airlines
11h 14mORD-OGG
5/13Mon
2 stopsUnited Airlines
15h 35mOGG-ORD
$503
5/10Fri
1 stopAlaska Airlines
30h 26mORD-OGG
5/17Fri
1 stopAlaska Airlines
33h 29mOGG-ORD
$524
8/8Thu
1 stopAlaska Airlines
20h 07mORD-OGG
8/13Tue
1 stopAlaska Airlines
20h 17mOGG-ORD
$534
5/14Tue
1 stopUnited Airlines
15h 03mORD-OGG
5/28Tue
1 stopUnited Airlines
11h 00mOGG-ORD
$560

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Recent one-way flight deals

5/13Mon
1 stopAmerican Airlines
10h 46mORD-OGG
$226
5/13Mon
2 stops
28h 16mORD-OGG
$249
5/13Mon
3 stops
28h 06mORD-OGG
$297
5/16Thu
2 stops
32h 40mORD-OGG
$306
5/18Sat
1 stopAlaska Airlines
19h 42mORD-OGG
$307
7/10Wed
1 stopAlaska Airlines
31h 52mORD-OGG
$322
5/18Sat
2 stopsDelta
13h 57mMDW-OGG
$336
7/11Thu
2 stopsDelta
18h 34mORD-OGG
$351
7/10Wed
2 stopsUnited Airlines
18h 43mORD-OGG
$373
4/23Tue
1 stopUnited Airlines
18h 40mORD-OGG
$398

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Last minute flights from Chicago to Maui

Last minute flight, train and bus deals

4/20Sat
multi-stop
20h 13mORD-OGG
4/26Fri
multi-stop
11h 53mOGG-ORD
$735
4/16Tue
multi-stopAlaska Airlines
11h 47mORD-OGG
4/25Thu
multi-stopAlaska Airlines
10h 38mOGG-ORD
$788
4/20Sat
multi-stop
22h 55mORD-OGG
4/26Fri
multi-stop
11h 53mOGG-ORD
$794
4/19Fri
multi-stop
26h 11mMDW-OGG
4/27Sat
multi-stop
24h 03mOGG-MDW
$823
4/16Tue
multi-stopDelta
15h 09mORD-OGG
4/25Thu
multi-stopDelta
10h 38mOGG-ORD
$879
4/18Thu
multi-stopDelta
14h 21mMDW-OGG
4/25Thu
multi-stopDelta
15h 20mOGG-MDW
$884
4/17Wed
multi-stopAmerican Airlines
12h 57mORD-OGG
4/27Sat
multi-stopAmerican Airlines
11h 34mOGG-ORD
$903
4/17Wed
multi-stopAmerican Airlines
14h 20mORD-OGG
4/27Sat
multi-stopAmerican Airlines
10h 36mOGG-ORD
$908
4/20Sat
multi-stopUnited Airlines
18h 19mORD-OGG
4/26Fri
multi-stopUnited Airlines
20h 57mOGG-ORD
$929
4/17Wed
multi-stopUnited Airlines
15h 29mORD-OGG
4/27Sat
nonstopUnited Airlines
7h 58mOGG-ORD
$1,102

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Flights to Maui

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Maui - Chicago

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$194
$314
$226
$32

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