$235 Find Cheap Flights from Chicago to Maui - Compare and Save

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Cheap Flights from Chicago to Maui

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Kahului
8h 56mNonstop
from $465per person
Hana
21h 32m4 stops
from $834per person
Kapalua
31h 08m4 stops
from $907per person
Booking Insights

KAYAK's insights & trends for Chicago to Maui flights

Get data-powered insights and trends into flights from Chicago to Maui to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Maui flight route?

The cheapest ticket to Maui from Chicago found in the last 5 days was to Kahului, at $651 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Kahului (OGG), and the cheapest round-trip airline ticket found on this route in the last 5 days was $651.

What is the cheapest time of day to fly to Maui?

The cheapest time of day to fly to Maui is generally in the morning, when round-trip flights cost $1,121 on average. The most expensive time of day to fly to Maui is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,121.

Can I save money by flying with a layover from Chicago to Maui?

No, with an average price for the route of $476, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Maui?

The cheapest month for flights from Chicago to Maui is January, when tickets cost $656 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,193 and $995 respectively.

What’s the cheapest day of the week to fly from Chicago to Maui?

When flying from Chicago to Maui, you should consider leaving on a Sunday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

How far in advance should I book a flight from Chicago to Maui?

To get a below average price on the flight from Chicago to Maui, you should book around 4 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

October

Cheapest flight

$235
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway 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 from Chicago to 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 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 from Chicago to Maui with an airline and back 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 from Chicago to Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago and Maui per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Maui, with an average flight time of 8h 56m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 1 flights.

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.

Reviews of the top 5 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.
8.0
SouthwestOverall score based on 4190 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

I paid extra to choose a seat. When arriving at the gate after a very stressful check in at the airport, realized did not get the chosen seat that I PAID for. When I called the airline I was told I did not pay to choose a seat and could not be refunded, but I DID pay extra to choose a seat. And of course, got stuck in a MIDDLE seat. Since the seats are now crammed together, this is especially uncomfortable. The check in for baggage was ridiculous, it was a mile long and the kiosk to check in for the flight was very confusing. We finally sought out help and a very rude representative quickly went through the kiosk and printed a boarding pass that did not provide the PAID for chosen seat. Didn't get to get on the return flight because the flight coming in was delayed several hours, missed the flight by 3 minutes!!!!!!! You really can't hold the door for 3 minutes for a passenger you KNOW you are waiting for??? What stress and had to wait 4 MORE HOURS to get a flight home because you could not keep the door open 3 minutes. 3 minutes. Had only 20 minutes to get from flight to connecting flight and was accused of taking too long to get from gate to gate in Chicago. Flights were delayed all day long coming in and going out, you would think you could wait 3 minutes to allow passengers to get to the connecting flights. HUGE inconvenience, stressful and makes for a really LONG day when the flight leaving Des Moines to Chicago was horribly delayed, already had a horrible experience and missed the connecting flight by 3 minutes. 3 minutes. Airplane was still there, the door closed, why on earth is it such a huge deal to wait a few minutes when flights were already delayed ALL DAY LONG and why is it such a huge deal to REOPEN the door to let another passenger on??!! I used to like Alaska Airlines. I just plain hate flying in general now. The airlines have 0 (zero)care about the people buying tickets and making travel plans and how stressful flying is now. Zero care.

They overbooked the flight! Or they said it was over weight, very unnerving as flying is a gamble anyway. They were waiting for six passengers to give up their seats, before they would board the flight, they were offering $1100. I’m guessing towards the purchase of the next ticket which I would never purposely fly with American Airlines. It was just the only flight available with what I needed. American Airlines is the top two worst airlines to fly with. And then after waiting an hour and four minute delay departing they ended up seating the people that they had asked to give up their seats anyway turns out they were not overweight after all. So all of that in a delayed flight and a delayed landing in Des Moines for nothing American Airlines is in competition with United Airlines for the worst airline to fly with.

The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Thanks for all you do to keep us safe and on time!

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

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

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

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

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

One thing you can always count on is your AA flight getting delayed. This is not surprising when they operate these planes like a greyhound bus with wings.

The seats cushion on my seat (exit row) needs to be replaced. It felt like I was sitting on a bar rather than a seat cushion. Also, I was in the middle seat and I sat next to an oversized guy (window seat) and he took up about 25% of my space. Otherwise, the experience was good. :)

The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.

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