$219 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 8/12. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maui, as well as popular online travel agencies
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Flights Deals

Best Maui Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului1 stop$437
Kahului
Kahului1 stop$437

Cheap Flights from Chicago to Maui

 
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, Aug 13 - Tue, Aug 19
American Airlines Logo
6:00 am - 11:34 amORD-OGG
10h 34m1 stop
American Airlines Logo
9:46 pm - 1:44 pmOGG-ORD
10h 58m1 stop
$437American Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
7:30 am - 4:56 pmORD-OGG
14h 26m1 stop
Delta Logo
9:10 pm - 5:57 pmOGG-ORD
15h 47m2 stops
$442Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 6:30 pmOGG-MDW
17h 00m1 stop
$454Southwest
Find Deal
Mon, Sep 29 - Mon, Oct 6
Alaska Airlines Logo
6:20 am - 1:15 pmORD-OGG
11h 55m1 stop
Alaska Airlines Logo
11:09 pm - 6:59 pmOGG-ORD
14h 50m1 stop
$456Alaska Airlines
Find Deal
Wed, Sep 3 - Mon, Sep 8
Southwest Logo
6:10 am - 4:30 pmMDW-OGG
15h 20m2 stops
Southwest Logo
8:30 pm - 3:55 pmOGG-MDW
14h 25m2 stops
$460Southwest
Find Deal
Mon, Sep 1 - Thu, Sep 11
Alaska Airlines Logo
6:20 am - 1:15 pmORD-OGG
11h 55m1 stop
Alaska Airlines Logo
12:45 pm - 7:03 amOGG-ORD
13h 18m1 stop
$461Alaska Airlines
Find Deal
Fri, Aug 15 - Thu, Aug 21
Hawaiian Airlines Logo
1:03 pm - 9:34 pmORD-OGG
13h 31m1 stop
Hawaiian Airlines Logo
8:00 am - 11:59 pmOGG-ORD
10h 59m1 stop
$526Hawaiian Airlines
Find Deal
Fri, Sep 5 - Fri, Sep 12
Hawaiian Airlines Logo
6:20 am - 1:15 pmORD-OGG
11h 55m1 stop
Hawaiian Airlines Logo
12:45 pm - 7:03 amOGG-ORD
13h 18m1 stop
$529Hawaiian Airlines
Find Deal
Mon, Jul 14 - Mon, Jul 21
 Logo
3:18 pm - 8:39 pmORD-OGG
34h 21m2 stops
 Logo
3:20 pm - 2:13 pmOGG-ORD
17h 53m1 stop
Mon, Jul 14 - Mon, Jul 21
 Logo
3:18 pm - 8:39 pmORD-OGG
34h 21m2 stops
 Logo
8:00 am - 2:13 pmOGG-ORD
25h 13m2 stops
Useful Info

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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Maui.

The cheapest ticket to Maui from Chicago found in the last 72 hours was to Kahului, at $913 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 $913.

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 $907, 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 September, when tickets cost $467 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $975 and $874 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 Wednesdays 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonMay
High seasonMarch
Cheapest flight$219
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 40% 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 evening, when round-trip flights cost $531 on average. Morning departures are around 115% more expensive than evening flights, 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 $1,142.

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.

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 10000 reviews
7.1Food
8.1Boarding
7.8Comfort
7.1Entertainment
8.5Crew
Airline reviews

Flight was delayed 5 hours. Missed connecting flight. Very little apology or attempt to make anything better. Got a $150 credit for next flight. There won’t be another flight. First time on Alaska - last time. Keep your credit. Should have done something more

2.0 MediocreMary, Jun 2025ORD - SEA
Read more Alaska Airlines reviews

Flight was delayed 5 hours. Missed connecting flight. Very little apology or attempt to make anything better. Got a $150 credit for next flight. There won’t be another flight. First time on Alaska - last time. Keep your credit. Should have done something more

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.

This flight was how a flight should be. The flight from Hawaii to Seattle was terrible

So much better coming back to Seattle than my trip TO Chicago. This crew actually communicated with the passengers!! Rebecca, one of the crew, stopped and visited with me about sign language. She should get a bonus of some kind!! She's a very neat gal!! It was still warm inside the plane, but it was packed! I still think you could do better than those teeny tiny pretzels! These were spicy and tasted terrible! All in all, still a better ride coming home. Go Seahawks!!

Arrival delay waiting for another flight to be towed and deboarded

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

Wish I got An email stating that I needed to check in at hawaiian even if I made my ticket thru alaska. I had to walk to terminal A from Terminal B.

Waited for an hour to take off with no reason for delay.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

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

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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.

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