$184 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 11/18. 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

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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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Cheap Flights from Chicago to Maui

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kahului
Kahului1 stop$464
Kahului
Kahului1 stop$464

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, Oct 30 - Sat, Nov 8
Alaska Airlines Logo
2:54 pm - 9:50 pmORD-OGG
11h 56m1 stop
Alaska Airlines Logo
11:59 pm - 11:59 pmOGG-ORD
20h 00m1 stop
$464Alaska Airlines
Find Deal
Tue, Nov 11 - Sun, Nov 16
Alaska Airlines Logo
7:59 pm - 10:50 pmORD-OGG
30h 51m1 stop
Alaska Airlines Logo
11:59 pm - 11:59 pmOGG-ORD
20h 00m1 stop
$466Alaska Airlines
Find Deal
Wed, Sep 17 - Mon, Sep 22
Delta Logo
7:10 am - 5:06 pmORD-OGG
14h 56m1 stop
Delta Logo
9:07 pm - 1:20 pmOGG-ORD
11h 13m1 stop
$488Delta
Find Deal
Wed, Oct 22 - Wed, Oct 29
Southwest Logo
6:05 am - 12:25 pmMDW-OGG
11h 20m1 stop
Southwest Logo
8:30 pm - 1:20 pmOGG-MDW
11h 50m1 stop
$491Southwest
Find Deal
Tue, Sep 16 - Fri, Sep 26
Delta Logo
7:10 am - 5:06 pmORD-OGG
14h 56m1 stop
Delta Logo
9:07 pm - 5:20 pmOGG-ORD
15h 13m1 stop
$491Delta
Find Deal
Thu, Oct 30 - Tue, Nov 4
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 3:00 pmOGG-MDW
13h 25m2 stops
$497Southwest
Find Deal
Thu, Sep 25 - Thu, Oct 2
Hawaiian Airlines Logo
6:20 am - 1:25 pmORD-OGG
12h 05m1 stop
Hawaiian Airlines Logo
8:00 am - 12:03 amOGG-ORD
11h 03m1 stop
$506Hawaiian Airlines
Find Deal
Wed, Sep 17 - Mon, Sep 22
 Logo
2:07 pm - 8:39 pmORD-OGG
11h 32m1 stop
 Logo
11:09 pm - 9:32 pmOGG-ORD
17h 23m2 stops
Fri, Nov 14 - Wed, Nov 19
Hawaiian Airlines Logo
2:54 pm - 10:50 pmORD-OGG
11h 56m1 stop
Hawaiian Airlines Logo
8:45 am - 12:24 amOGG-ORD
11h 39m1 stop
$512Hawaiian Airlines
Find Deal
Mon, Oct 13 - Wed, Oct 22
 Logo
6:50 am - 10:05 pmORD-OGG
44h 15m2 stops
 Logo
8:00 am - 11:59 pmOGG-ORD
10h 59m1 stop
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 $833 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 $833.

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 $926, 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 November, when tickets cost $552 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $986 and $851 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 Sundays 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, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$184
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 37% 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 109% 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 $1,112.

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 10000 reviews
7.0Entertainment
7.1Food
7.8Comfort
8.1Boarding
8.5Crew
Airline reviews

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

2.0 MediocreAnonymous, Aug 2025ORD - SEA
Read more Alaska Airlines reviews

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

Terrible. Would never fly again. Took them several hours to prepare the plane and and reached my destination 4 hours late.

Our boarding was delayed due to two flat tires, but I appreciate the focus on safety. I also appreciated the additional offerings for drinks which never happened before except on Hawaiian Airlines. The hospitality is fantastic! Glad I upgraded to premium seats for the extra leg room as I was getting frustrated when the person in front of me was very restless and kept shifting. Otherwise, it was a fantastic experience.

Had to sit and wait to get off the plane for closeto a hour. My son also flying to a different destination that day also had like a 2.5 hr delay

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

Could not check in online - had to get boarding passes at the ticket counter and our daughter got bumped off our connecting flight. NOT OK!

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I needed more space to sleep on an overnight flight.

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

I could not believe that on a 5 hour plus flight we were not given a complimentary meal . That should be illegal. Or it would be nice to be informed beforehand that a complimentary meal would not be provided. The wording in the email I got about pre ordering food was phrased in a way that made the food seem like it would be free. Very misleading! Also during boarding we were informed there would be empty seats we could move to if we wanted, all we had to do was wait for an announcement, however an announcement was never made. Then when we tried to change seats ourselves we were singled out over the loud speaker and told we could not move without asking. Then the flight was about to take off , so we didn’t have time to ask . Then we were told we could not move to the exit row because you had to pay for those seats, but we were not told where we could move. Also no one was in the exit rows so , if something happened no one would be there to assist the passengers. Also people should be allowed to move there if the airline wasn’t able to sell them. One passenger asked if he could pay for the upgrade and the flight attendant said she did not have the capability to charge for the seat on her mobile device, so the airline ended up losing possible income anyways . So why not let people move there during flight if you have no way to charge them? Then the landing was bumpy and awful and many passengers complained out loud when we landed .

The flight was great! The flight attendants were friendly and attentive. I would definitely fly Hawaiian Aurlines again!

You have to buy the ear buds and they only offers little cup of water twice.

Flight was on time, crew was friendly and prompt with the service. The only thing that could be improved is the seat space, but that's wishful thinking

Cons: Rode a newer Airbus - had the same rattle in the panels above my seat (plastics not secure b/t lighting and panels) as the last Airbus I rode. Cabin was quite warm, borderline hot. Asked to pay for headphones. And the reason I am writing this - when we arrived it took over 20 minutes to get our door open due to nobody on the ground ready for arrival. Likes: Staff was friendly, helpful, and professional. Sandwich was quite good.

The worst flight experience I've ever had. Our flight was delayed 14 whole hours because the flight crew never showed up. We had to wait in a two hour line to get our new boarding passes, we were told we had no other option but to fly at 10pm (we didn't depart until 11:45pm). Everyone had to contact their hotels and car rental places, workplaces, etc. since we lost an entire day's worth of travel. The crew showed up at 10:15, which was past the time we were supposed to board. They were laughing and being completely smug when they boarded, and they took another hour to board us onto our flight. The flight crew never came to check in on us, we were quickly given one drink and sandwich and they turned off the lights and were negligent the rest of the trip. My mom asked three attendants for a seat belt extender, they never brought one. I was dehydrated and never received another drink. They were very rude and unfriendly, we had been up since 4am the morning of our flight and didn't land in our destination until 2am the next day (5am local time). This was unacceptable service and treatment, these flights are not cheap and we were inconvenienced out of an entire day of travel. This was 100% avoidable and was the fault of Hawaiian Airlines, and their crews inability to show up to work on time.

Loved the leg room, usb charging, outlet, food, staff. The seats were very uncomfortable for some reason and made my buttocks ache and would have liked to be seated together from the time of purchasing tickets without having to pay extra.

Usually we have a pleasant trip on HA. Not this time! All stewards were unpleasant, rude, rushed, condescending. First step onto the plane, WE greeted the crew with an “Hello!”. They greeted us with a terse smile then ignored us. Not a good start. Even over the PA announcements, they were rushed and unpleasant. One Stewart even berated a passenger in front of us when all they asked is if the purchase cart had vodka to purchase. The steward said “LIKE WE SAID OVER THE PA, THIS ONLY HAS FOOD OR BEVERAGE!” Vodka is a beverage! It was a legitimate question. Not sure why she treated the passenger this way. Taking trash was even unpleasant, No “Thank you” or at least a smile. I work in CS. I know good CS can make or break your trip. There was absolutely no “aloha” on this trip. All clearly did not want to be on this plane and felt strongly that they did not want to provide a premium service to their clients. This might be our last HA and cancellation of my HA-MC if we are treated the same way going home. We are typically treated with kindness and warmth in the past with HA. This trip was unacceptable.

Overall it was a good flight, but the food should be looked at. No options. The seat was also uncomfortable and very tight.

It’s great, I’ve always fly & ride with Hawaiian Airlines going Inter island or to the mainland.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

Everything you need to know for your flight to Maui

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