$172 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 3/9. 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.
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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

Thu, Feb 26 - Wed, Mar 4
Multiple Airlines Logo
8:20 am - 6:51 am
ORD
-
OGG
26h 31m
2 stops
Multiple Airlines Logo
11:54 pm - 11:59 pm
OGG
-
ORD
20h 05m
1 stop
$408Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
8:20 am - 10:00 pm
ORD
-
OGG
18h 40m
2 stops
Multiple Airlines Logo
11:02 pm - 7:03 pm
OGG
-
ORD
15h 01m
1 stop
$409Multiple Airlines
Sun, Mar 1 - Thu, Mar 12
Alaska Airlines Logo
3:07 pm - 11:46 pm
ORD
-
OGG
12h 39m
1 stop
Alaska Airlines Logo
10:54 pm - 11:59 pm
OGG
-
ORD
20h 05m
1 stop
$412Alaska Airlines
Mon, Feb 23 - Tue, Mar 10
Multiple Airlines Logo
8:20 am - 10:21 pm
ORD
-
OGG
18h 01m
2 stops
Multiple Airlines Logo
7:49 pm - 2:58 pm
OGG
-
ORD
14h 09m
2 stops
$413Multiple Airlines
Sat, Feb 28 - Mon, Mar 9
Alaska Airlines Logo
8:20 am - 11:46 pm
ORD
-
OGG
19h 26m
1 stop
Alaska Airlines Logo
10:54 pm - 11:59 pm
OGG
-
ORD
20h 05m
1 stop
$414Alaska Airlines
Wed, Feb 18 - Fri, Feb 27
Alaska Airlines Logo
3:07 pm - 11:46 pm
ORD
-
OGG
12h 39m
1 stop
Alaska Airlines Logo
2:04 pm - 11:59 pm
OGG
-
ORD
29h 55m
1 stop
$415Alaska Airlines
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
5:05 am - 12:50 pm
MDW
-
OGG
11h 45m
1 stop
Southwest Logo
8:55 pm - 12:35 pm
OGG
-
MDW
10h 40m
1 stop
$422Southwest
Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m
1 stop
Delta Logo
12:59 pm - 8:53 am
OGG
-
MDW
14h 54m
2 stops
$428Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m
2 stops
Delta Logo
12:59 pm - 8:53 am
OGG
-
MDW
14h 54m
2 stops
$433Delta
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
5:05 am - 12:50 pm
MDW
-
OGG
11h 45m
1 stop
Southwest Logo
8:55 pm - 12:35 pm
OGG
-
MDW
10h 40m
1 stop
$453Southwest
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 $844 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 $844.

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 $411, 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 $598 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $953 and $924 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 Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

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 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$172
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 22% 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.

  • 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 $1,096 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 $1,096.

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
Alaska AirlinesOverall score based on 11807 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.0Entertainment
7.1Food
Airline reviews

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

4.0 OkayTimothy, Jan 2026
LAX - OGG
Read more Alaska Airlines reviews

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.

I behave had better flights this one was old and poor

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

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

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

I was very, very cold and a stranger loaned me her sweater next to me. I didn’t wanna buy a blanket just for a four hour trip when I did not need the pillow or the earphones. I don’t mind purchasing a blanket, but I only needed that not all of it accessories. Cold air pretty much blew the entire trip. Two people in front of me both bought the blanket packages. Maybe that’s the idea. The crew was exceptionally nice and passed through multiple times.. the restrooms were very clean and usually accessible.

3 hour wait on customer service after flight was cancelled. Was bumped to a flight where I wouldnt have gotten to my destination for another 2 days. Had to fully refund flight and book a new one the following morning. Paid twice the amount for the flight than I had originally booked. Very disappointed I was not offered any sort of discount or points for all of the frustration, in fact the airline profited twice as much off of me by cancelling my flight and and changing my entire trip.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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.