Find cheap flights from Chicago to Maui

Find cheap flights from Chicago to Maui

Round-trip
Economy
Chicago (CHI)
Maui
Fri 1/15
Fri 1/22
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Maui

Good to know

Low season

January Best time to beat the crowds with an average 4% drop in price.

High season

December Most popular time to fly with an average 6% increase in price.

Average price round-trip

$799 (avg. price over the last 2 weeks)

Good deal round-trip

$529 or less

Good deal one-way

$318 or less

Top tips for finding cheap flights to Maui

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to Maui is March.
  • Morning departure is around 10% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Maui flights

Which airlines have a flexible cancellation policy for flights from Chicago to Maui due to COVID-19?

How long is the flight to Maui from Chicago?

What is the cheapest flight to Maui from Chicago?

Which airlines fly to Maui?

Are there Maui travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights 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?

What is the Hacker Fare option on flights to Maui?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Maui?

Top 4 airlines serving from Chicago to Maui

Scores according to KAYAK customer reviews

8.3
Alaska Airlines
Overall score based on 29,231 reviews
8.5
Boarding
8.3
Comfort
8.8
Crew
7.9
Entertainment
7.9
Food
Airline reviews

Pros: "Time of flight is not delayed and arrival time is even ahead of the estimated time."

Cons: "Auxiliary generator broken so plan got hot very quickly. Flight was 2.5 hrs delayed due to another mechanical failure. And then once we were in air they generously notified us that the WiFi was broken. Utter garbage."

Pros: "Nothing."
Cons: "We were sitting in the plane on the tarmac for 3 hours waiting to take off. The crew did a very poor job announcing what was going on."

Pros: "Not much"
Cons: "Just about everything"

Cons: "Slowest boarding process of my 3 Alaska flights today"

Pros: "Nice and friendy crew, and it seems I can always hear the pilots on Alaska. On other airlines, they are hard to hear. Alaska pilots were pleasant to listen to, as well. Comfortable seats and good leg room at back of plane."
Cons: "My seat was full of crumbs when I boarded, hair was sticking out of the magazine in front of me. I wish there was some cleaning/disinfecting of the plane prior to a new flight boarding. It's flu season and that's exactly what I got 2 days after flying home. I gave the food and entertainment 1 star as I didn't use either. Should be a NA option."

Pros: "First time flying Alaskan. Out of all the US-based airlines I flew with, Alaskan was the cleanest, friendliest, and quickest."

Pros: "Free movies!"

Pros: "We arrived half an hour early! Bags on time."

Pros: "Snacks are good and crew is very friendly. Kept us up to date with arrival times. Would fly again with Alaska"
Cons: "With delta, the movies are free. Didn't like that I had to pay for certain entertainment on Gogo"

Pros: "Our ticket handler at Alaska Airlines ( Sep 21- SMF Airport) was the most helpful and patient person we have ever encountered! The tickets we had purchased through Kayak were charged but not booked. Juan did everything in his power to get us on that flight. And when the kayak company failed to book in time Juan got us on the next available flight, being to sure to find us the best price and a direct flight, versus the one we had booked earlier. Over all Alaska Airlines will be the standard my future experiences will be based off of if I am unable to travel through them"

Pros: "Same as above"
Cons: "Same as above"

Pros: "Very accommodating staff"

Pros: "It was fast and friendly. They took a lot of guesswork out and made us feel safe."
Cons: "The planes were a bit small for flying 6+ hours. I started getting restless at having to sit in the same position for that long."

Pros: "The staff was extremely pleasant. Plenty of leg room. Departed on time and arrived ahead of schedule."
Cons: "Nothing."

Cons: "We were asked to exit the plane at Tarmac and I was traveling with 2 little children. There were a lot of stairs to get off the plane and then walk back to terminal and then a lot of stairs were there to get back to terminal. I was hurting in my knee and my kids ears were hurting badly because the pressure was not controlled while landing. It was a very bad experience and I will definitely think twice about flying Alaska again."

Pros: "Captain's flight commentary good Crew fine. Plane fine."
Cons: "slow, untimely, disorganized boarding Couldn't get seat assignment online or at airport."

Pros: "On time"
Cons: "Not enough freebies"

Pros: "Boarding was fast"
Cons: "Space between the rows is narrow, I understand it has nothing to do with the flight itself."

Pros: "The flight crew supplied plenty of drinks throughout the flight."
Cons: "Those seats are just never comfortable in economy class. They need lumbar adjustment."

Pros: "Flight service kept things light and friendly, efficient. Although the takeoff was late, attempts were made to shorten the flight so that overall delay was minimized on the back end. Thank you!"
Cons: "Can't think of anything."

Pros: "Great service and extremely friendly staff. Brand new plane. More economy legroom then other carriers"

Cons: "This flight was first delayed, then not listed on the reader board. Then the flight added a stop over in Seattle for the the only reason that the crew was maximizing their allowed time to work. This delayed arrival at final destination. They could have brought on a fresh crew in Chicago but they did not do that."

Pros: "noting they suck"
Cons: "they where late taking off because one of there stewardess was late one hour ....HORRIBLE SERVICE....."

Pros: "It was pretty good. This was my first Alaska Airlines flight. Seattle to Maui was better than Newark to Seattle. First flight was uncomfortable. Seat did not recline. Didn't try the food. I took Virgin to Newark from Maui, and Alaska on return. I had high expectations from Virgin, but I liked Alaska better."

Cons: "A child crying the whole trip behind my seat. No effort by mother to stop child from crying"

Pros: "Arrived on time even tho it took off late."
Cons: "I don't believe I was offered the chance to reserve a better seat when I made my reservation."

Pros: "Friendly, caring, and knowledgable staff"
Cons: "No hot food choice on 6+ hour flight."

Pros: "Getting off the Plane."
Cons: "There were not enough Breakfast meals, and I could not eat anything that WAS available... You should have At Least enough of the Daily meal, or whatever you call it, for all the passengers... especially at Breakfast.... everybody wants Breakfast. AND... maybe try not to sit single adults in the middle of 3 screaming toddlers. I hate kids. and that was REALLY ANNOYING. - and I was not allowed to move due to the Load Weight so... It pretty much all sucked. and then - & I know this is out of your hands - but this was all n top of bad turbulance... Worst Flight I hve ever been on, and I am a Travel agent, and practically grew up on Airplanes."

Pros: "Boeing plane was so comfortable and modern and new."

Pros: "I fly this route regularly and Alaska is my first choice - the service is good, and everyone gets a celebratory drink prior to landing in the Islands. I will often upgrade to 1st class, and that is so worth it. I arrive at my destination after 5 hours feeling relaxed and able to jump right into the new environment."
Cons: "In 1st class - no complaints whatsoever. In coach - the usual: seats small, cramped, packed in with hundreds of other human beings, just waiting for it to be over. What a difference between the two!"

Pros: "The crew and passengers were friendly. The most fun I've had in a plane in a long time!"
Cons: "Nothing! It was great!"

Cons: "I had tried multiple times to get a seat at the ticket counter and at the departure gate...when I was finally able to get a seat there were no aisle seats available...that was not helpful as I am required to get up every 1.5 hours and walk around the cabin because of health issues Beverage service was once and no snacks..I am used to this so brought along some snacks but it would have been nice to have peanuts and not only a cold drink but then some coffee."

Cons: "No room for my carry on bag! Had to check it. Not good. Had a tight timeline. Upon arrival at ORD was told bags would be at carousel 2/3. This was confirmed by Alaska personnel at ORD after exiting plane. Waited for 25 minutes. No bag. Inquired again with Alaska personnel at baggage claim. Was told bags were at carousel 5. Huh? Screwed up my evening plans."

Pros: "Best price"
Cons: "On display travel info"

Pros: "Almost everything was pleasant, easy. The crew was especially nice and very helpful."
Cons: "I realize you are doing your best to make the cost of traveling as reasonable as possible and that making the seats quite narrow plays a big part in this goal however, I am very grateful the gentleman sitting next to me on the way to Maui was not only pleasant but was not offensive in any way. He did, however, kind of overlap the armrest so that I was squished against the other armrest. A very slender lady sat next to me on the way home. Made it a more comfortable trip. Jan"

Pros: "The turkey sandwich I had was made with actual sliced turkey, not deli meat. This was a treat for airplane food, and it wasn't very overpriced. It was also a very spacious, comfortable flight. The crew were very friendly and helpful. Alaska is definitely one of my preferred airlines."
Cons: "The flight was a little longer than it normally is, but I think there were some strong winds which slowed it down."

Pros: "Friendly, professional, easy going & helpful staff. Comfortable seats, with plenty of leg room (I'm slim and 5"6"). I like that carry-on bags can easily be checked at the gate (when flights are full), and that there is no penalty for doing so."
Cons: "Boxed meal (Mediterranean Tapas) was missing an item that was listed on the menu."

Pros: "I was given a surprise upgrade after a very long week. It was amazing! The flight crew was fun and they took excellent care of me. Thank you so much."

Pros: "Polite staff, awesome service."
Cons: "We would enjoy free wifi even if we can't have free movie streaming."

Cons: "I cancelled my flight, and although I purchased flight insurance, still ended up having to do a bunch of paperwork and losing money. After experiencing cancellations on other flights, this was by far the worst. The $150 cancellation charge on Alaska is unbelivable and the insurance KAYAK provided through Allianz was awful."

Pros: "Efficient, friendly service"

Pros: "Boarding and seating were good."

Pros: "Food!"

Pros: "All of the staff were very accommodating and incredibly nice. From check in addressing us by our first names, to how quickly we were able to access our bags when we landed. My wife and I travel fairly frequently and we found all of our flights (each 5 hrs min.) were very pleasant and would recommend this airline to anyone considering traveling."

Pros: "A seatbelt that could not be fixed? This is your excuse for every difficulty I've had in the last 25 hours."

Pros: "Seats comfortable"
Cons: "Huge delay with little communication. Waited on plane close to 2 hours before leaving gate. Flight very rough. Landing terribly rough. Crew seemed angry. Cleaning of plane minimal between flights. Did not recycle. Downstairs loading area in Chicago was a little unnerving"

Pros: "Great crew!"
Cons: "Just had a super delayed flight and lost one of my luggages."

Pros: "This was my first time flying with Alaska Airlines and it was a smooth flight. I loved it!!"

Pros: "The crew was very nice and helpful, I had a nice spot on the plane, and it went very smoothly, especially considering the circumstances. I was supposed to be flying to Seattle later on, but I had to change my flight last minute because of the virus. The whole Delta team was very understanding and considerate and it made the process much less stressful."
Cons: "My flight was cancelled and rescheduled for a later time the day before and there was a lot of changing of gates and running around, but I understand that everything has been hectic and I don’t blame that on you, I know you’re all doing your best."

Pros: "We left on time"
Cons: "The size of the plane is just so bad"

Pros: "The airplane seats and entertainment were 150% bettter than American"
Cons: "The check in area felt cramped, understaffed and like a 4th rate airline"

Cons: "Delayed for an hour because of changing tire"

Pros: "The crew was absolutely amazing. I was HORRIBLY ILL the entire 6.5hour flight, vomiting LITERALLY every 15minutes in the bathroom. They took care of me in every way possible. You have no idea how THANKFUL I WAS AND AM FOR THEM. SO MUCH ALOHA FROM HAWAII, best flight crew EVER!!! PLEASE reward them"
Cons: "If I wasn't deathly ill right before I had to get on the flight!"

Cons: "Mechanical difficulty. Late Then missed connecting flight. 4 hours in a hotel. Then back to the airport the next day. Why can’t airline keep planes in good condition?"

Pros: "The crew was amazing! They were all so nice and helpful"
Cons: "The WiFi didn’t work"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Cons: "Delayed 2 hours, huge inconvenience"

Pros: "Fly attendants were very professional"
Cons: "Nothing"

Pros: "Attendant was friendly and efficient."
Cons: "No beverages or snacks."

Pros: "Excellent hospitality I asked for a cup of coffee at an odd time, the attendant went out of his way to brew fresh pot and served me, instead of just saying "Sorry sir, we don't have any coffee at this time....""

Pros: "There were minimal passengers on the flight so I was able to have the entire row to myself. The flight was also very short which is always nice."
Cons: "N/A"

Pros: "Good snacks. Nice crew. Nice seats."
Cons: "Pay WiFi? JetBlue does it for free.."

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Cons: "Was not allowed to check in even tho flight was delayed. Horrible!"

Cons: "There was no rhyme nor reason for who boarded first"

Cons: "Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?"

Pros: "Friendly service. Frequent snacks which is nice on a 10-hour flight."
Cons: "Cramped conditions"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Call back service was best part."
Cons: "Booked ticket through venture card points. This meant that the email address and phone number to contact us in the event of changes was mediocre information. I was informed from Tripit that the flight was delayed, not by Delta. Reservation personnel took logical course of action to find new flight for connection that we could make because of delayed initial flight. I would recommend that they first see if there is an earlier initial flight that the customer could make, then look at finding later connecting flights. We found out about delay 8 hours prior, so we had plenty of time to get to the airport earlier. Total delay required me to take additional day off of work."

Pros: "Once we finally boarded, it was fine- plane was new and clean and entertainment system was great. Agents did the best they could with limited information on flight status. Provided snacks at departure gate- but they were all unhealthy."
Cons: "Flight originally booked with 2:30pm departure time, was pushed to 4:30pm a few weeks in advance. Then the flight was delayed on the day by 30 minute intervals until 9pm. Finally, we were switched to a different gate to board a different plane. Then sat on the plane at the gate for another hour so they could load all the bags. We didn't take off until 10:30pm- painful."

Pros: "Great customer service"
Cons: "Nothing"

Pros: "Crew members were very nice and friendly and dealt with the desire for passengers to switch seats in a very nice way even with annoying passengers."
Cons: "Sadly due to turbulence there was no beverage service and a very rushed snack service which I know wasn't their fault but just overall flight okay."

Cons: "Haven't left yet!!!"

Pros: "anaheim"
Cons: "luggage did not arrive same time with me and not the same airport"

Pros: "Being on time."

Pros: "The flight was on time."
Cons: "This was an almost 6 hour long flight, LAX to OGG. The aircraft was older and for a 6 hour flight, they really should use a bigger and newer aircraft. The entertainment systems on the back of the seat worked sporadically and the PA system was too loud and every time the PA system was used while we had our headsets on, it was excruciating We had no warning in order to remove our headsets before it blasted into our ears. We were amazed that after paying a considerable sum for our tickets and being in the air for 6 hours, there was limited meal service and we were required to purchase a sandwich in order to eat. I fly Delta frequently and this was by far the worse flight I can remember."

Pros: "Friendly staff staff, smooth boarding experience, DC+ positive experience"
Cons: "757-200 outdated for having spent 10 hours on that same plane (stop but no plane change) having flown shorter haul flights on many updated 757 was disappointing."

Pros: "None of it!! Poor selection"
Cons: "All of it. Again poor selection"

Pros: "The entertainment"
Cons: "We didn't get our seat assignment until we got to the gate. Attendant said it was because tickets bought too close to take off don't get to pick seats, but we bought our tickets about three weeks before. Also, my boyfriend and I sat in a full row while the row in front of us only had one person. It would've made more sense to put that person in one of our seats and us in that row to give four people more space instead of just one."

Pros: "Early boarding for family. Flight crew was decent"
Cons: "Super cramped seats. Entertainment system was broken. Only small snacks and drinks for a 5.5 hour flight"

Pros: "The staff was very helpful and kind."
Cons: "The wifi did not work, my seatbelt was literally broken/unattached, they had no coffee. This may seem minor to some but when you are at the airport at 4 a.m with a child you don't expect all yhese things to happen."

Pros: "Nothing more than expected."
Cons: "Food could be improved."

Pros: "Had a great experience on my flight. All on time, and connections were great."

Pros: "Tv on flight"
Cons: "Flight attendant skipped me for drinks"

Pros: "Seating was nice...comfortable. Lighting was good, captain wasn't too chatty :)"
Cons: "This flight attendant was just terrible. Wish I could remember her name for this review... She had about half of the First Class cabin offended as soon as meals started getting served - I didn't see ANYONE around me that got what they asked for, and then when people stated the issue, she didn't respond very well. I tried to take things in stride (first world problems?) but it is a bummer to pay extra for the first class treatment and then to not have that great experience, especially on back to back 5ish hour flights."

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Speed of birding and departure. Very smooth ride on the 777."
Cons: "Not many food options."

Pros: "Everything was smooth from start to finish, and the flight landed 10 min. early! Can't ask for more!"

Pros: "Delta fed us so well. They made sure we were as comfortable as possible. The flight attendants were nothing short of kind and always smiling. Even the pilot was very ethusiastic over the intercom before the flight. He made jokes and everyone laughed. In fact, it was the most I've ever heard from a pilot on any flight in my life. I would rate this the best flight I've ever had. Thanks, Delta!"

Pros: "This was a 767 and we flew first class, so we had the more private, reclining seats with the advanced electrical and USB outlets. The flight attendants were excellent and I had a special meal request, which they confirmed and served me well."
Cons: "Nothing. the flight was great!"

Pros: "It was actually a flight from new Orleans to Detroit. Seats were assigned at the gate for myself and many others. It seemed like the gate agent didn't care where she assigned guests who were travelling together as several people were not able to sit with their travel companion. Once I was on the plane I however switched with someone to allow them to sit next to their companion and put me closers to mine. Everything else went smoothly."

Pros: "Quick boarding"
Cons: "The delta comport seats were not comfort seats were hardly comfortable and the leg room wasn't worth paying for."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "The check in personnel was fantastic - very helpful and friendly with a very relevant story that made me feel more relaxed. Our not so good seats were somewhat compensated by the plane staff that gave us each a full beverage can, extra pretzels, and some cookies."
Cons: "Our seats that we'd picked out seemed to get changed when we checked in and we got out in the last row, which had no window, and smelled strongly of bathroom cleaner."

Pros: "Skyprority was great along with the perks of PE seats. Crew, as usual, were professional, pleasant, and organized."
Cons: "IFE was great but remove the games component from the menu. I had a child poking the screen playing the game for 3 hours and everytime they poked the screen it moved my head as if she was just hitting the back of the steat. PE seats really don't offer that much more room and the seat on the 757-200 vs 9 was AWFUL! My tailbone hurts 24 his later."

Pros: "Cheapest flight to Cyprus"
Cons: "Dirty, cramped, and they neglected to send my luggage on from Amman."

Pros: "Got to watch movies"
Cons: "Couldn't eat the meal both had dairy no other choice"

Pros: "Exit row seat very roomy with plenty of leg room."
Cons: "Flight from ORD to LGA delayed even though the plane was already at the gate in ORD. No announcement explaining why it was delayed. What was worse was that after landing at LGA, baggage tagged as Priority did not come out first, it came out much later - after numerous non-priority baggage came out. This is not the first time this has happened at LGA. What's the point of tagging it as Priority if it won't be handled that way?"

Cons: "This agent spent 30+ min to check us in through a connection flight to Seattle. He couldn't find my wife's reservation, when it should be in the same reservation as me. He tried 5 times, and still failed. Later we found out at the gate that he was using the wrong name (same last name, different first name). Luckily the American Airline agent at the gate was more than competent and efficient to correct the issue in 5 min."

Cons: "Horrible delays. Delta doesn't have these problems."

Pros: "Always delayed. Always check my carry on. Which equals me being late to where I'm going."
Cons: "See above"

Pros: "The plane left on time"
Cons: "Attitude of personnel on plane Plane was old and in need of up grading No service, you have to ask for a cup of coffee and they give it to you as it is a favor Keep inventing reasons to make it more difficult to achieve any level. They invented a platinum """""Pro""" level that used to be Platinum and downgraded the platinum level so they provide less perks"

Pros: "Food was decent, service was okay"

Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."

Pros: "thay we didn't crash"
Cons: "1. To didn't work 2. Give us pillows"

Pros: "Crew was very nice. Free snacks provided on plane."

Pros: "United airlines canceled a flight last minute that I needed in order to get to my best friends' wedding on time, I usually fly AA but the United flights were slightly cheaper at the time. The options United gave me would have had me missing the wedding, AA had more flights that allowed me to make it in time, considering it was booked 12 hours before take-off, it was decently reasonable and left on time and got in early (imagine that, United). Thank you American Airlines, again!"

Cons: "Surprisingly, AA provided the worst experience of the overall itinerary, compared to Aer Lingus and Iberia. The AA plane was outdated, cramped legroom - despite having purchased an "upgraded seat" and departed 1hr late"

Pros: "on time"
Cons: "very cold"

Cons: "The entertainment system in my seat was broken. Was a bummer since we added a extra hour ground hold for weather."

Pros: "Once I made it, they worked to get me on the plane from Chicago quickly."
Cons: "I barely made it for my flight in Chicago and that was with running. They were already boarding the other plane when my plane from Hattiesburg landed. Earlier in the day I had to get them to change my flight from Chicago in Hattiesburg because it wasn't changed for me when the delay had my original flight leaving before I was to land in Chicago. I don't fault them for someone getting sick at the last minute or my inconvenience, but it was still inconvenient."

Cons: "Tsa is very unorganized and extremely rude."

Pros: "In flight movie options are great!"
Cons: "We boarded about an hour late but that happens."

Pros: "NOT much!"
Cons: "My window seat was right against the right engine. I could feel the vibrations and noise. It seemed like an old plane. I was definitely miserable on this flight. Very!"

Pros: "I appreciated the American Airlines crew at the gate in Chicago, who helped us to get two seats together. The flight crew was excellent as well."
Cons: "Not being able to choose our seats beforehand."

Cons: "it was an hour late"

Pros: "Was listed on-time up to 20 minutes before boarding. Then the departure time kept getting pushed back until we departed two hours late"
Cons: "If there is a delay, I'd rather them just be up front in estimating the time of the delay."

Pros: "In your Chicago office. He was extremely helpful both to us (too older ladies) and to others. Please thank him for us and look at him for a promotion. I think he may work for American Airlines instead of British Airways."

Pros: "First class flight attendant was awesome!!"

Pros: "Actually, I like that it was late because my first flight arrived late. The flight overall was very quick and smooth."
Cons: "The seats were covered in crumbs from the previous flight, but that's probably because of the hurry to get passengers on to the next flight because the plane was late."

Pros: "Staff was very nice; very courteous."
Cons: "We were delayed for 2 hours! I had a premium seat but still ended up boarding with Group 6. Almost ran out of room and had to check my roller. Not happy with late boarding given that when I booked my ticket, it said I'd have priority seating."

Pros: "All connections-smooth"

Pros: "We did not take this flight when its schedule was moved back, instead taking one LHR-SEA that would get us home at a reasonable hour."
Cons: "The change by British Air in flight departure/arrival times. The resulting adjustment was costly and we were unable to get "extra" seating on the long leg of the trip by the time we were notified of the changes."

Pros: "More options for entertainment on a long flight."

Cons: "one of the worst trip ever. although there were many turbulances, the captain did not appear to be proficient along the way. The landing was horrible as well."

Cons: "Ground crew was inadequate and unorganized. Ground crew caused a late flight to be even later. Plane was overbooked and the ground crew was more interested in filling the flight than accommodating Advantage Member seating."

Pros: "When we arrived, we found the plane was changed, and our seats were in the middle, and separated. We had paid extra to have window seats.. After speaking to one of the gate attendant ( Arturo ), he went out of his way to accommodate us, and we ended up with great seats. Friendly and accommodating crew! ."

Pros: "worst experience. Airplane people not so good"

Pros: "The crew was courteous and very nice."
Cons: "The aisles are too narrow. As passengers are boarding and you sit in the aisles you are constantly struck. FAA should investigate with the decreased aisle width and distance between the seats, can the evacuation be completed within required time, in an actual emergency. American Airlines is endangering the lives of passengers. And the cramped conditions are contributing to the hostile actions of some passengers. What does it take to do what is right?"

Cons: "Forced to check my carry on. Took 30min for the bags to come out on the carousel. Which is why i never check my bag."

Cons: "I like milk. Also space out drink service and offer tea and coffee periodically."

Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."

Cons: "I took the bus from Ohare to Gen Mitchell airport because of delay at Ohare. No crew, again."

Cons: "Lovely flight, but onboarding groups were a nightmare. Given the chaos, they started forcing bags to be checked early."

Pros: "Friendly crew"
Cons: "3 hour delay"

Pros: "Exit row seating."

Pros: "No individual screens to watch. Get with the times for long flights !"

Cons: "My outbound flight to Manila had an overnight layover in Japan. I asked at the luggage check-in at O'Hare International Airport if they can check it all the way through as I had planned to go outside of the Narita airport for the layover. They told me I couldn't check the luggage all the way through and that I had to pick it up from baggage claim once I land in Narita. From there I had to check-in the luggage again on the same day. When I took my luggage out from baggage claim, I tried to check-in and the counter crew told me I was given wrong information. I had to keep my luggage with me until my flight the following day. On my return flight from Manila and another overnight layover in Narita, the check-in crew at NAIA told me I could check-in my luggage all the way through, and that they also allowed this at my outbound flight to Manila. The check-in crew at O'Hare International Airport gave me wrong information."

Pros: "Flight was straightforward and crew were pleasant."
Cons: "The boarding process was not so good. It was a busy flight and they needed to put luggage underneath asking for volunteer, then after a certain point it was mandatory. I completely appreciate the need for it to happen, but it turned into caos. People everywhere stood waiting. My suggestion would be to have people who need to check baggage stand off to the side and continue boarding those who are ready to go."

Pros: "Ok flight"
Cons: "Not iberia"

Cons: "I was unable to get this flight and rebooked onto a United flight that was denatured 4 hours."

Cons: "Return flight was delayed, gate changes unfriendly and unhelpful flight attendants"

Pros: "Nothing"
Cons: "Thought it was funny I didn't get a survey about my disaster trying to leave Boston, only the on time flight getting back. 6 hour delay leaving because of a warning light they didn't catch to begin with. Missed a whole day of vaca. No help once they deplaned us. Horrible flight. First time on American too. Paid for a window seat specific and had no window."

Pros: "Boarded plane on time"
Cons: "Plane looked old and beat up. Sat in plane at jetway for a 45 minute maintenance delay."

Pros: "nothing"
Cons: "everthing"

Pros: "Timeliness"
Cons: "It was a NINE hour flight and there was NO FOOD provided!!! Why do we have to pay extra for the crappy food??"

Cons: "Seats too narrow."

Pros: "United Airlines Flight 202 Left on time. It was a Boeing 777 so it had a lot of room."
Cons: "The flight attendants seemed focused only on the small First Class section and rushed through everything in the Economy Class. They rushed through the "Food Service" and didn't want to answer questions about what is on their menu. The menu was removed from the magazines in our row. Fortunately, we brought our own snacks. The Economy CLass cabin had a terrible odor. It really smelled. Maybe they should clean the plane once in a while. United Airlines ALWAYS has issues with entertainment. You MUST download their App to your cell phone. Then, they allow you to connect to their entertainment system. If you don't, you cannot access WiFi without paying $26 for the flight ... the WiFi access is inconsistent and limiting and doesn't always work so the download doesn't always complete. This was a nine hour flight from Hell. I think I prefer Frontier Airlines. Although the airlines make you pay for everything now, at least you expect some attention and food options and a plane that doesn't smell. It was nauseating. Don't even ask me about the "Miles" that they keep screwing up ... RAY HANANIA"

Cons: "Nothing"

Pros: "First flight on a 777 ... quiet and comfortable."
Cons: "It's a long day in a plane but necessary if you want to travel to bucket list destinations!"

Pros: "Flight was on time."

Pros: "Flight itself was fine. Major delay resulted in arriving one day later than planned, additional transportation cost, unplanned, and unplanned parking fees. No travel voucher was offered and when I asked was told it was not possible to issue a travel voucher."

Pros: "The flight was good..."
Cons: "No entertainment was available ... even do they announced ..."

Pros: "In flight entertainment. Was able to watch a movie for free."

Pros: "Flight on time and arrived early"

Pros: "That I finally got there a day later. I only had carry on bags, so they weren't lost."
Cons: "At OHare the gate agent sent me to the wrong gate and plane for my flight. I did not arrive Thursday at 8:30 pm as scheduled. Customer service put me on "red eye" to Dulles for the next flight to Charleston, without motel or meal vouchers. I couldnt sleep on the benches there due to asthma and diabetic issues. I arrived Friday 2:30 pm 17 hours late. Dulles overnight cleaning staff helped more than agents at OHare."

Pros: "Good crew"
Cons: "Shitty seats was very uncomfortable probably won't fly United just because of that... Delta has a lot more comfortable seats"

Pros: "Seats were nice and crew was friendly"
Cons: "It wasn't their fault but we did have to land at a different airport due to weather, but it showed that the crew took safety first"

Pros: "Excellent service and friendly staff"
Cons: "Absolutely not enough room to stretch your legs"

Cons: "Some inspector idiot decided that the exterior cover stickers weren't "up to code" literally half an hour before my flight, delaying us 2 hours. I got onto a different flight at the last second, then the same thing happened to that plane. Brilliant on their parts. I almost lost a job interview thanks to your people."

Pros: "same as above"
Cons: "same as above"

Pros: "Getting to Charlotte"
Cons: "Plane dirty. Windows dirty. Extremely bumpy. Seats clostraphobic. Sat too long leaving"

Pros: "The flight crew apologized and kept everyone informed."
Cons: "The plane was having mechanical problems. Once it was determined that the problem couldn't be fixed it took the airline quite some time to locate a new plane. They should have started working to identify a new plane sooner. Ended up arriving in Portland after 3 am."

Pros: "Overall fine"

Pros: "flight was excellent"
Cons: "Monitor kept running commercials and a show i couldn't hear very annoying"

Pros: "Plane was on time"
Cons: "Plane was crowded and seats were small and crammed"

Pros: "The seats were perfect, a lot of leg room. Comfortable side pillows on the seats"
Cons: "All the rest including the absence of food"

Cons: "Why should I have to pay to watch tv? I know you don't have to pay on Southwest, Virgin America or Jet Blue. Not sure that a very (and I mean VERY SMALL) snack can be considered food"

Pros: "On time, gates were close together"

Pros: "Comfy environment, not completely booked plane"
Cons: "The price for one little bottle of Rum, highway robbery I say."

Cons: "The plane was delayed."

Pros: "Newer plane. Very nice staff"
Cons: "Floor around seat was dirty. Lot of exaggerated braking. Suggested a new pilot perhaps?"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Deverted to Newark to get to portland"

Pros: "Duration of flight was shorter than expected. Arrived at destination fifteen minutes early."
Cons: "No complaints."

Pros: "Good"

Cons: "Delayed because there was no crew to fly the plane switched gates 6 different time other than that everything was good"

Pros: "I was incredibly disappointed that my luggage got sent on an earlier flight to Memphis from Chicago. When I arrived in Memphis after 24 hours of flying, I found my luggage locked up and no representative to be found. Exhausted, frustrated, and seeing my luggage through the glass door and not being able to retreave it, I was incredibly frustrated with United. If you are going to send luggage on a different flight, be there and available to let travelers claim their luggage. My entire flight had gotten their bags from baggage claim before I even found someone available to open the door. I had to get an American Airlines representative to call them to the area twice before they arrived. If you are going to do this, offer the traveler to be on the earlier flight too. I was very disappointed, especially after my flight was delayed by 45 minutes on top of it."
Cons: "The poor customer service."

Cons: "Never made it so I can't rate it"

Pros: "Everything went smoothly"

Pros: "Crew was nice"
Cons: "Flight was delayed. Food was terrible"

Cons: "Delays both ways"

Pros: "On Time, polite smiling crew, happy passengers, overall excellent."

Pros: "Totally on time: excellent everything. This was a smooth flight both ways."

Pros: "Flight wasn't full"
Cons: "Flight was delayed an hour due to maintenance repairs."

Cons: "There should be some free tv"

Pros: "Crew was able to switch my seat so I was able to board early and have a seat where I could stretch my bad foot."
Cons: "On takeoff and landing it sounded like the plane was falling apart - literally. My confidence was shaken when it sounded like someone was sawing the belly of the plane. Very scary."

Pros: "Everything!"

Cons: "Many hours of delays from and to.."

Cons: "Had an extended overlay because of an overlap booking with our pilot. He was on another plane that wasn't due to come in until two hours later."

Pros: "Smoothly and on time"

Pros: "Willingness to check carry ons for sold out flights"
Cons: "Choosing of seats process. My traveling partner and I did not get to sit together on way home. Everyone was nice and got a free upgrade but would have been nice to sit together"

Pros: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"
Cons: "My mother is disabled and was assigned wheelchair assistance and does not speak English very very hopeful does not have a cell phone because she is disable and does not know how to use a cell phone I was calling the one 800 number for united airlines they gave me a phone number for the terminal where she was delayed and I was just trying to check to see if my mother was aware of what was going on with the delay I just need to know if my mother was OK to give her comfort but unfortunately the number they gave me was not working I was calling over 30 rings with nobody answering for over three hours O'Hare airport was very hopeless for united airlines it's a shame that that is their head quarters i'm pretty sure I will never ever use United Airline again in my life after the terrifying experience I had waiting over four hours from my mother besides the four hour flight I was very terrified until my mother was in my arms I never ever want to experience that again or I hopefully nobody ever that uses your United airline will ever experience that"

Pros: "Good customer service"

Cons: "When about to get on plane, carry on taken to checked bags; 5 people already on plane were required to come back off and check bags. I begged not to have to check because I was flying to Nicaragua and was worried my only bag would get lost. I was right -- it did not arrive in Nicaragua until the next day. We sat on runway for 45 minutes before departure so United could fix BOTH sets of the plane's wings lights. Why did they not discover that at any time BEFORE we all boarded or while we were boarding -- NOT first when deciding to pull away from gate. Delay caused many to miss connections."

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from Chicago to Maui

Airlines flying from Chicago to Maui have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Maui

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Maui

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Maui

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Maui

Book cheap flights from Chicago to Maui

Recent round-trip flight deals

1/26
Tue
2 stops
Multiple Airlines
33h 35m
ORD - OGG
2/2
Tue
2 stops
Multiple Airlines
28h 14m
OGG - ORD
1/26
Tue
2 stops
Multiple Airlines
33h 35m
ORD - OGG
2/2
Tue
2 stops
Multiple Airlines
28h 14m
OGG - ORD
1/26
Tue
3 stops
Multiple Airlines
33h 44m
ORD - OGG
2/2
Tue
2 stops
Multiple Airlines
28h 14m
OGG - ORD
1/26
Tue
2 stops
Multiple Airlines
25h 45m
ORD - OGG
2/2
Tue
2 stops
Multiple Airlines
20h 16m
OGG - ORD
1/26
Tue
3 stops
Multiple Airlines
35h 48m
ORD - OGG
2/2
Tue
3 stops
Multiple Airlines
25h 06m
OGG - ORD
2/14
Sun
2 stops
Multiple Airlines
27h 34m
ORD - OGG
2/18
Thu
2 stops
Multiple Airlines
15h 32m
OGG - ORD
2/7
Sun
2 stops
Multiple Airlines
26h 29m
ORD - OGG
2/18
Thu
2 stops
Multiple Airlines
15h 32m
OGG - ORD
1/26
Tue
1 stop
Multiple Airlines
27h 55m
ORD - OGG
2/2
Tue
2 stops
Multiple Airlines
20h 16m
OGG - ORD
2/14
Sun
2 stops
Multiple Airlines
27h 34m
ORD - OGG
2/25
Thu
2 stops
Multiple Airlines
15h 32m
OGG - ORD
2/2
Tue
2 stops
Multiple Airlines
25h 45m
ORD - OGG
2/18
Thu
2 stops
Multiple Airlines
19h 53m
OGG - ORD
2/22
Mon
2 stops
Multiple Airlines
32h 00m
ORD - OGG
3/1
Mon
2 stops
Multiple Airlines
30h 06m
OGG - ORD
2/14
Sun
2 stops
Multiple Airlines
27h 34m
ORD - OGG
2/22
Mon
2 stops
Multiple Airlines
14h 15m
OGG - ORD
4/28
Wed
1 stop
Alaska Airlines
30h 10m
ORD - OGG
5/10
Mon
1 stop
Alaska Airlines
14h 18m
OGG - ORD
4/7
Wed
2 stops
Delta
17h 22m
MDW - OGG
4/14
Wed
2 stops
Delta
16h 38m
OGG - MDW
1/22
Fri
2 stops
Delta
19h 31m
MDW - OGG
1/25
Mon
2 stops
Delta
19h 57m
OGG - MDW
4/13
Tue
2 stops
Delta
17h 22m
MDW - OGG
4/20
Tue
2 stops
Delta
16h 38m
OGG - MDW
4/28
Wed
2 stops
Delta
17h 22m
MDW - OGG
5/3
Mon
2 stops
Delta
16h 38m
OGG - MDW
2/12
Fri
2 stops
Delta
19h 36m
MDW - OGG
2/15
Mon
2 stops
Delta
19h 57m
OGG - MDW
4/22
Thu
2 stops
Delta
17h 22m
MDW - OGG
4/29
Thu
2 stops
Delta
16h 38m
OGG - MDW
5/3
Mon
2 stops
Delta
17h 22m
MDW - OGG
5/17
Mon
2 stops
Delta
16h 38m
OGG - MDW
Show more results

Recent one-way flight deals

1/20
Wed
3 stops
Multiple Airlines
25h 54m
ORD - OGG
2/7
Sun
2 stops
Multiple Airlines
26h 29m
ORD - OGG
1/31
Sun
2 stops
Multiple Airlines
26h 29m
ORD - OGG
2/8
Mon
2 stops
Multiple Airlines
50h 29m
ORD - OGG
2/7
Sun
2 stops
Multiple Airlines
30h 25m
ORD - OGG
2/22
Mon
2 stops
Multiple Airlines
59h 14m
ORD - OGG
1/27
Wed
2 stops
Multiple Airlines
34h 46m
ORD - OGG
2/1
Mon
2 stops
Multiple Airlines
42h 30m
ORD - OGG
4/8
Thu
1 stop
United Airlines
15h 36m
ORD - OGG
2/1
Mon
1 stop
United Airlines
32h 03m
ORD - OGG
1/20
Wed
2 stops
United Airlines
28h 18m
ORD - OGG
4/8
Thu
2 stops
United Airlines
27h 40m
ORD - OGG
2/5
Fri
1 stop
American Airlines
13h 42m
ORD - OGG
2/5
Fri
2 stops
American Airlines
19h 01m
ORD - OGG
2/4
Thu
1 stop
American Airlines
13h 42m
ORD - OGG
2/6
Sat
2 stops
American Airlines
17h 55m
ORD - OGG
2/20
Sat
2 stops
American Airlines
24h 14m
ORD - OGG
2/23
Tue
2 stops
United Airlines
31h 46m
ORD - OGG
4/7
Wed
2 stops
Delta
17h 22m
MDW - OGG
2/12
Fri
2 stops
Delta
19h 36m
MDW - OGG
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First