$247 Find Cheap Flights from Chicago to Maui

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 5/28. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maui

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

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

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

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

Flight Deals
Booking Insights
Flight Deals

Book Cheap Chicago to Maui Plane Tickets

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

Wed, Sep 16 - Thu, Sep 17
Multiple Airlines Logo
6:01 am - 9:41 pm
ORD
-
OGG
20h 40m
2 stops
Multiple Airlines Logo
6:00 am - 11:41 pm
OGG
-
ORD
12h 41m
2 stops
$499Multiple Airlines
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
6:50 am - 12:35 pm
MDW
-
OGG
10h 45m
1 stop
Southwest Logo
8:35 pm - 4:15 pm
OGG
-
MDW
14h 40m
2 stops
$500Southwest
Wed, Aug 26 - Wed, Sep 2
American Airlines Logo
12:11 pm - 9:19 pm
ORD
-
OGG
14h 08m
2 stops
American Airlines Logo
1:16 pm - 7:16 am
OGG
-
ORD
13h 00m
1 stop
$500American Airlines
Tue, Sep 15 - Fri, Sep 25
Multiple Airlines Logo
7:00 am - 5:49 pm
ORD
-
OGG
15h 49m
2 stops
Multiple Airlines Logo
6:00 am - 11:41 pm
OGG
-
ORD
12h 41m
2 stops
$505Multiple Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
6:00 am - 1:26 pm
ORD
-
OGG
12h 26m
1 stop
Multiple Airlines Logo
10:30 pm - 6:50 pm
OGG
-
ORD
15h 20m
1 stop
$509Multiple Airlines
Tue, May 26 - Tue, Jun 2
United Airlines Logo
6:13 am - 12:34 pm
ORD
-
OGG
11h 21m
1 stop
United Airlines Logo
1:04 pm - 4:51 am
OGG
-
ORD
10h 47m
1 stop
$510United Airlines
Wed, May 27 - Thu, Jun 4
Multiple Airlines Logo
2:18 pm - 8:45 pm
ORD
-
OGG
11h 27m
1 stop
Multiple Airlines Logo
6:00 am - 11:55 pm
OGG
-
ORD
12h 55m
2 stops
$514Multiple Airlines
Tue, Sep 1 - Tue, Sep 8
Multiple Airlines Logo
2:18 pm - 9:38 pm
ORD
-
OGG
12h 20m
1 stop
Multiple Airlines Logo
10:51 am - 6:22 am
OGG
-
ORD
14h 31m
2 stops
$515Multiple Airlines
Thu, May 28 - Thu, Jun 4
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
Delta Logo
9:05 pm - 5:56 pm
OGG
-
MDW
15h 51m
2 stops
$521Delta
Fri, May 29 - Mon, Jun 8
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
Delta Logo
1:05 pm - 8:37 am
OGG
-
MDW
14h 32m
2 stops
$551Delta
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Maui from Chicago found in the last 72 hours was to Kahului, at $894 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 72 hours was $894.

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

The average price for all round-trip flights from Chicago to Maui depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Maui is generally in the morning, when round-trip flights cost $1,073 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 $1,073.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $443, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Maui, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Maui is October, when tickets cost $220 (return) on average. On the other hand, the most expensive months are November and August, when the average cost of round-trip tickets is $402 and $401 respectively.

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

The average price of all round-trip flights from Chicago to Maui clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Maui, you should consider leaving on a Tuesday and avoid Fridays 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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Maui, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$254
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 20% 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 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.

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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maui. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4314 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

You can standby to get on earlier flight if the seat is open.

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

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

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

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

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.

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I always love flying Hawaii and I have nothing to add

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight to Maui

Cabin class types available on flights to Chicago

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.