Find cheap flights from Chicago to Hawaii

Find cheap flights from Chicago to Hawaii

Round-trip
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Chicago (CHI)
Hawaii
Tue 1/26
Tue 2/2
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Good to know

Low season

August Best time to beat the crowds with an average 3% drop in price.

High season

December Most popular time to fly with an average 9% increase in price.

Average price round-trip

$761 (avg. price over the last 2 weeks)

Good deal round-trip

$506 or less

Good deal one-way

$314 or less

Top tips for finding cheap flights to Hawaii

  • 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 Hawaii is March.
  • Morning departure is around 21% more expensive 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 Hawaii flights

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Top 3 airlines serving from Chicago to Hawaii

Scores according to KAYAK customer reviews

8.3
Alaska Airlines
Overall score based on 29,234 reviews
8.5
Boarding
8.3
Comfort
8.8
Crew
7.9
Entertainment
7.9
Food
Airline reviews

Pros: "She was cute, really acted like she liked her job! Left early and arrived early."
Cons: "I wanted a candy bar instead of the mai tai"

Pros: "On time did not have to wait long at all for luggage."

Pros: "Professional flight attendants"
Cons: "N/A"

Pros: "On time. Crew was friendly, helpful. Seats slightly more comfortable than most."

Pros: "Loved how smooth it ran,such a professional crew,really made the time pleasant.i really wish all my flying times could be like this one,I would highly recommend this airline to all my friends,family and work partners,the crew was well verse in key Hawaiian words and very polite on departure."
Cons: "I think it would be to difficult to try and come up with anything,maybe I could say that the chicken was a little over cooked but that's it"

Pros: "worst flight ever on Alaska air. paid full fare first class and treated like a freeloader. hate to see their reputation go downhill. but like most airlines now, they are not interested in the premium customer. Ill go back to Delta..."

Pros: "Crew was very helpful and entertaining. We left about 5 minutes late yet arrived early. 2 rounds of drink service and cookies for about a four hour flight. Tablets available for rent as well as wifi. Would fly Alaska Airlines again"

Pros: "The flight attendants went above and beyond!"

Pros: "check in at ohare was super easy. Also no security line. Friendly Staff."
Cons: "After push back we waited for about half an hour before we moved to the runway."

Pros: "Great food options..excellent service, even a free Mai Tai!"
Cons: "Seat sizes are small but not too bad. If a 1st class upgrade was available, I would've done it!"

Pros: "The hand held pc's loaded with movies was very cool. The crew was exceptional The sequence of the meal service was very good"
Cons: "The first class seats were not very comfortable, have traveled on various competitors in first and these seat were the first to cause me shoulder and neck discomfort (note this is the first time that Ive traveled in first on AS) The lunch main meal meat were over done, my wife had the chicken and I the pork both were dry as a desert."

Pros: "The flight was over AC'd and we froze. We asked the FA's three times to turn it down. They don't care."

Pros: "Great captain and crew"
Cons: "Need newer movie selections"

Pros: "I was in first class so that's the better experience. I would have been even unhappier in coach."
Cons: "Seat, despite being first class, was not comfortable I asked for a blanket before takeoff and was told there aren't any on board. No blankets for an 8 hr red eye??? No pillow either. Flight attendants never asked if I wanted another beverage after initial service. It was an 8 hr flight. The first class meal was a tiny cheese plate. I was starving. For a $900 1 way ticket, I expect more of this airline Flight attendants seemed like they didn't want to be there. Wasn't feeling the love. it was a 12:30am flight. We are all tired, but c'mon. Smile a little."

Pros: "Staff was great."
Cons: "Food options just ok. Seats super small"

Pros: "We didn't crash."
Cons: "Cheap seats, food, everything we mediocre..."

Pros: "Great flight. On time, good weather"

Pros: "Everything"
Cons: "Nothing"

Pros: "flight was good and on time"
Cons: "in flight entertainment ok but cant use it with out apps that you cant"

Pros: "I try to book Alaska when I can, they have good leg room for a taller person and their baggage fees are not outrageous like Spirit. You can tell the crew is not completely miserable doing their jobs and treat you like a human most of the time."

Pros: "Very friendly staff, on time and professional."

Pros: "It was on time and 30 minutes early to our destination!"
Cons: "Nothing"

Pros: "Comfort,service , and plane all great !"

Pros: "Left early, arrived early"
Cons: "Tell me about the entertainment software before we get to the airport."

Pros: "The boarding process was unhurried and they offered free checked bags to keep the overhead storage from overflowing."
Cons: "The noise level in the cabin was high. I'm glad that I have Bose noise-cancelling headphones."

Pros: "Flight attendants, mai tai."
Cons: "Late plane"

Pros: "Great Flight Attendants"
Cons: "No light snack with beverage. Was told company forgot to put on plane. Could also be we were in last row of plane and may have run out. Last row of plane was very cramped. I was in middle. Attendant felt bad enough did not charge me for the glass of wine I ordered."

Pros: "Very friendly crew. The airline also offers a little more leg room than other airlines"
Cons: "Small crowded terminal at O'Hare made boarding seem chaotic"

Pros: "It was a little confusing beacause your brochure said I would have free Wifi so I didn't rent your tablets. A half hour later I realized the wifi doesn't actually work, so I missed out on renting your tablets to watch something. I think there should be a less confusing system. This is more of an Alaska Airlines gripe though."

Pros: "Flight personnel were focused and expedient. We arrived on time."
Cons: "First time flying Alaska outside of the Mainland. For a five hour flight, surprised there were no complementary meal service. Only beverage cart services. Flying five hours to Maui, Hawaii is a bit different than a 1 hour flight to Portland or Seattle. Price of Alaska economy ticket no less than their next competitor (i.e., Hawaiian Air, etc.) on the same flight route offering meal service. May want to rethink pricing model?"

Pros: "Love the amount of space availabile for my legs!!"

Pros: "The crew was fantastic! I was on my way to my bachelorette party in Portland and they were so sweet, congratulating me and even giving my friends and I free drinks! I would definitely fly them again! LOVED IT! :)"

Pros: "leg room on premier seats. Entertainment had big variety and high quality."
Cons: "No food on 5 hour flight unless you pay"

Pros: "Friendliness"

Pros: "The flight attendants made quite a few passes through to make sure everyone had drinks."
Cons: "We were very delayed in taking off because the copilot wasn't there. Many people had connecting flights and the crew did nothing to help them get off the plane first or give any kind of reasrrances that they could make the flight."

Cons: "Two days before flight online seating chart showed no seats available that were together in main cabin so I bought "economy plus" seats. There were actually 32 empty seats in economy, many people had while rows to themselves. What a ripoff."

Pros: "The flight attendants made our flight very nice. They went out of their way to take care of us."
Cons: "Nothing"

Pros: "Loved the idea of the entertainment. Loved the food and drink options."
Cons: "Movie was interrupted every 10 mintutes by a buggy sign-in interface. Tray was dirty when I first put it down. Legroom was not sufficient."

Pros: "Everyone was so kind, thoughtful and timely."
Cons: "Our seats didn't recline, making it hard to rest."

Cons: "The seats where to crowded"

Pros: "Nice crew and yum cheese plate"
Cons: "Late boarding and late arrival."

Pros: "Best staff, rivals Hawaiian. Arrived 7 min early."

Cons: "There was no entertainment (movies) on this long flight. Not an issue for me, but I know other airlines typically do have them."

Pros: "Every single customer service representative I encountered at the airport or on the plane was very polite and just generally and genuinely in a good mood. Flight was exceptionally on time."

Pros: "Alaska does everything it can right, and does offer elites media players. The flight was in about 40 minutes early."
Cons: "Alaska reduced the size of first."

Pros: "Crew was pleasant."
Cons: "Smelled like someone snuck a long-dead rodent into the cabin. Hard to endure for a 4+ hour flight."

Pros: "Flight on time. Great service"

Cons: "My initial flight was at 0800; I got to the gate before 0800 and was told I couldn't board the flight even though it was still at the gate and was still before the flight time. I had to pay to rebook my flight, spent over $200 in rides to and from airport, had additional parking fees and was several hours late to work. I have many family members who work in flight service so I understand that employees don't like to re-do paperwork; however, being there before the flight time and being denied cost a lot of work time and money. I have always had great experiences with Alaska so this one was quite a disappointment compared to their usual great service. :("

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

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: "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: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."

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: "The crew was great. The seats, though cramped, were nice to have electronic device holders instead of built in screens."
Cons: "The flight was 9 hours and they didn't provide any meals. That's ridiculous. When I fly with any other airline for over 7 hours I've always gotten 1 meal, if not 2. The food for purchase however, was very good. But they should not expect you to pay."

Pros: "The crew was outstanding and landing was smooth Very welcoming"
Cons: "I wish they would give us more snacks But overall it wa fantastic"

Pros: "I like that United flys 777 to Hawaii. I specifically look for the larger AC when I am booking my trip. Secondly the Flight crew was efficient and very helpful as always"
Cons: "None"

Cons: "Plane sat on runway & subsequently returned to gate due to mechanical issue resulting in 2.5 hour departure delay. Boarding was chaotic - flight attendant said procedure not consistent with UA practices. Food only available is purchased from UA, and what food was available ran out (I never did get fed on the 11+ hour flight). Cabin very cold."

Pros: "quick overall flight"
Cons: "No food options other than purchased snacks on an 8-9 hour flight"

Pros: "The crew were friendly."

Pros: "The crew was exceptionally friendly and helpful. Water and drinks were offered regularly. For those who had the app there was inflight entertainment. We paid for plus size seats and had enough leg room."
Cons: "I believe that on the long flights built in entertainment screens should be standard. Most people did not have the app and many spent 8.5 hours without anything to do. Food is not offered on this long flight unless you pay for it. You must walk to the very back of the plane where the food is in warmers. I got a hamburger and it was a bit dried out. Could have been worse...just hard to handle since tomato, lettuce and condiments were on the side. A larger person sat next to me and took use of the armrest between us which made me feel like I lost 4 inches of my personal space."

Pros: "Everything was great except for entertainment."
Cons: "Wi-fi wouldn't work on my phone or iPad. What an extremely long trip with no entertainment. Hopefully it works in the flight baCj home :/"

Pros: "The crew of this flight were amazing, attentive, and so positive. They certainly made the long flight an enjoyable one. The only challenge was that the in-flight entertainment stopped working 5 hours into the flight. That said, the crew informed us of how United would compensate us for that. As for the landing, that was perfect. We eased onto the tarmac so gently it barely felt as though we had landed."
Cons: "I wasn't too excited that the in-flight entertainment quit working about five hours in, but the crew did their best to remedy the situation. It did stink that we were delayed in disembarking, but that wasn't the fault of the crew. Lastly, I do wish that food came complimentary with it being a 9-hour flight. The options presented were tasty looking but it felt a little like we were being nickeled and dimed."

Cons: "While going inside the flight they told me there is no room for Carryon and gave me ticket to book the luggage. When I went inside the Flight there is lot of room to carryon's, why they have to lie this BS."

Cons: "The crew no food no pillow no blanket"

Pros: "We'll coordinated."

Pros: "I liked the Lufthansa flights using Airbus Aircraft the entertainment system is the best."
Cons: "The entertainment system on the boeing planes is not necessarily the best, the screens are smaller, the selection of movies is not upto date and even Live TV does not work"

Cons: "See above comments."

Pros: "In flight entertainment was great!"

Pros: "The comfy seats"
Cons: "The fact that I had to pay to watch tv. Maybe people should have to pay for movies, but not for watching tv. Flights and till we takeoff can take a while. It would be nice to have some free entertainment. The plane was very hot when we were boarding."

Cons: "The seats are tiny. If you drio something, you can't reach down to pick it up. The food was burnt. The app isn't downloadable in China. The overall experience makes me not want to ever fly United again."

Cons: "Entertainment and food could have been better."

Pros: "Excellent as expected."

Pros: "Good entertainment for a long flight."
Cons: "A power jack could come handing."

Pros: "United got me from point A to point B"
Cons: "Crew was rude, not just to me, but to other patrons. Flight was packed going and the man scanning boarding passes spoke to those of us asking simple questions as if we were stupid and defiant. Was he a prison guard in his previous job? On the way to Newark, I had an aisle seat. One of the stewardesses blazed by me with a cart ramming it into my shoulder without so much as a, "sorry." I'm not a big woman but maybe as I dozed off I leaned over a bit...There is no way she didn't feel her cart hit me. Rudeness, it seems is a part of the culture at United because the flight attendants coming back squeezed past the long line for the bathroom without saying, "excuse me." They did however, say, "I need to get by," and one of them brushed by the gentlemen sitting next to me and bumped his laptop and coffee. Overall it seems that the crew working these particular United flights have forgotten that we pay hard earned money to fly. Some of us are going on vacation, to see loved ones, and some are flying to deal with unpleasant circumstances. The staff may fly several times a day, but most passengers do not. There's a lot of prep and anxiety, that goes into taking a flight and a surly flight crew multiplies that anxiety. No one wants to fly with a crew that hates their job."

Pros: "The flight overall was great, easy to board and de-board, and a smooth process from start to finish."
Cons: "Connecting to the in-flight wi-fi to watch movies and tv shows was nearly impossible."

Pros: "Loved that it was an empty flight"

Pros: "The service was good"

Pros: "Friendly flight attendants, helpful staff at the ticket counter."
Cons: "Unable to check into both legs of my flight even though Air Canada used United for the first leg."

Cons: "Two hour delay for start of engines.. Not enough chichen and pasta was not good"

Pros: "The flight was a head of schedule and very smooth."
Cons: "It was freezing cold. I was wearing a sweater and was freezing."

Pros: "I have metal leg braces. The staff was helpful getting me from terminal to terminal. They were very helpful."
Cons: "Having a leg brace makes difficult I am blessed I can move a little without them. I had to move a short distance without my brace. No place to put it back on."

Cons: "i missed my flight because my flight left Toronto late"

Pros: "Pilot was very happy and friendly! Very informative throughout flight."
Cons: "On the return home, I was seated in the last row right next to the lavatory. I was bumped into at least 40 times by other passengers and flight attendants."

Pros: "not a damn thing"
Cons: "Weather delays are a typical part of travel. What's not typical are 5+ hour delays and sitting on the tarmac and watching your connection take off without you. First Class seats morphed into Economy center seats the next day, with nary a hotel room in sight. Thanks for nothing."

Cons: "The flight was very hot and uncomfortable!"

Pros: "Nothing"
Cons: "This flight never happened it continued to get canceled and canceled!!"

Cons: "seats were very uncomfortable"

Cons: "We got on board, waited 20 minutes. Capt said it was a bad reverser, and we were waiting on paperwork for 15 minutes. Long story short, they make us leave the plane after 2.5 hours. Then we wait in the airport for another 2.5 hours. I missed my connection and spent 10 hours in Chicago."

Pros: "The flight attendant finally took care of it after I complained a couple of times."
Cons: "That you changed our seats, and, that there was no room in any of the overhead bins. So, the flight attendant told me that I needed to fight my way through the people coming toward me back up the aisle and check every overhead bin all the way back up to see if there was room for my one suitcase. Others had brought more than one bag up there. Finally they checked my one carry on bag. The ride was also really bumpy, worst that we've ever experienced. But that was due to weather conditions."

Cons: "Everything! Even worse than my previous flight. Delays were inexcusable, staff ridiculously unfriendly and just bad attitudes all round. Very unpleasant experience, won't be using this airline ever again."

Pros: "Nice clean plane, very friendly and helpful crew."
Cons: "The hour delay."

Pros: "The crew was fantastic despite the entertainment system wasn't working"
Cons: "The entertainment and wifi was nonfunctional for the 8 hr flight."

Pros: "Pre-check with United"
Cons: "Did not get connecting flights boarding pass from the beginning. Short connection time - was very stressful"

Cons: "Couldn't reserve/request a seat. Assigned to me About 1.5 hours prior to boarding. Had to wait Around the gate. Should have told me I would not have any choice. Could have walked around. Got a middle seat. It was a long flight."

Pros: "The flight attendant was great! Pleasant, polite and professional!"
Cons: "The flight from ORD to ABE was on a plane with expired maintenance logs or inspections? We were delayed 2 hours in arriving for what seemed like a pilots lax in paperwork. But what does a customer expect from an airline who knows they that customer by the balls?"

Pros: "Great boarding at ORD."
Cons: "My seat"

Pros: "Movie selection and delivery/access was very good"
Cons: "Seat legroom is insufficient. There was a water leak in the ceiling that dripped cold Wster on me for a portion of the trip."

Cons: "The flight was late by 5 hrs due to mechanical problems. The gate crew was confused about what to do and we ended up with several deboardings and boardings. Food was terrible. The entertainment system did not work."

Pros: "Everything else was fine"
Cons: "For such a long flight and quite expensive some food should be provided. I have never flown before like that (over hundreds of overseas flights) and had NO FOOD given at all."

Pros: "the flight attendant crew was super nice throughout the entire flight."
Cons: "the tvs weren't working for the all the seats, and the food was not very tasty."

Pros: "Flight itself was good. Nice flight attendants. Funny pilot."
Cons: "The lady at desk to board the flight made me check my carry on. I had assumed it was because the plane was full, but when I got on the plane there were more than adequate spots to stow more bags. There was a compartment across from my seat that remained open the entire flight. While I completely understand the need to check extra luggage when the plane is full, I was very upset when I saw it was not. I intentionally fly with a carry on for the convenience, and to be inconvenienced for absolutely no reason made me not want to fly with this company again for fear it could happen again in the future."

Pros: "The flight crew was very helpful and organised the connection between two flights very well under pressing circumstances when there was only 15 min between the flights and the boarding gates being in opposite ends of a big Munic airport"
Cons: "The flight was delayed for 2 h, so we had to run through Munic airport for connected flight. Good sport, but rather tiresome."

Cons: "8 channels of looped shows and movies. Too long a flight for that...and then have to use my device to watch on the free part of the wifi.so no battery left. For this price? And I booked through Lufthansa but flew United. Bad form."

Read more about Alaska Airlines
COVID-19 information

Safety measures for airlines flying from Chicago to Hawaii

Airlines flying from Chicago to Hawaii 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 Hawaii

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Hawaii

Pre-flight testing

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Book cheap flights from Chicago to Hawaii

Recent round-trip flight deals

2/22
Mon
2 stops
Multiple Airlines
16h 13m
ORD - OGG
3/1
Mon
2 stops
Multiple Airlines
21h 34m
OGG - ORD
2/23
Tue
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/1
Mon
2 stops
Multiple Airlines
21h 34m
OGG - ORD
2/28
Sun
2 stops
Multiple Airlines
16h 13m
ORD - OGG
3/1
Mon
2 stops
Multiple Airlines
19h 32m
OGG - ORD
2/23
Tue
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/2
Tue
2 stops
Multiple Airlines
19h 32m
OGG - ORD
2/15
Mon
2 stops
Multiple Airlines
17h 23m
ORD - OGG
2/22
Mon
2 stops
Multiple Airlines
20h 45m
OGG - ORD
3/1
Mon
2 stops
Multiple Airlines
17h 44m
ORD - OGG
3/11
Thu
2 stops
Multiple Airlines
19h 51m
OGG - ORD
2/21
Sun
2 stops
Multiple Airlines
16h 13m
ORD - OGG
2/25
Thu
2 stops
Multiple Airlines
29h 15m
OGG - ORD
3/3
Wed
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/9
Tue
2 stops
Multiple Airlines
19h 51m
OGG - ORD
2/21
Sun
2 stops
Multiple Airlines
16h 13m
ORD - OGG
3/2
Tue
2 stops
Multiple Airlines
19h 32m
OGG - ORD
2/24
Wed
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/8
Mon
2 stops
Multiple Airlines
18h 13m
OGG - ORD
3/9
Tue
2 stops
American Airlines
28h 19m
ORD - LIH
3/18
Thu
2 stops
American Airlines
17h 58m
LIH - ORD
3/20
Sat
1 stop
Alaska Airlines
27h 35m
ORD - LIH
3/28
Sun
1 stop
Alaska Airlines
26h 44m
LIH - ORD
3/10
Wed
1 stop
Alaska Airlines
16h 30m
ORD - LIH
3/18
Thu
1 stop
Alaska Airlines
26h 44m
LIH - ORD
2/23
Tue
1 stop
Delta
16h 50m
ORD - LIH
3/2
Tue
2 stops
Delta
14h 36m
LIH - ORD
2/23
Tue
2 stops
Delta
16h 35m
ORD - LIH
3/2
Tue
2 stops
Delta
14h 36m
LIH - ORD
2/17
Wed
2 stops
Delta
19h 41m
MDW - HNL
2/24
Wed
2 stops
Delta
16h 40m
HNL - MDW
2/22
Mon
2 stops
Delta
16h 43m
MDW - KOA
3/1
Mon
2 stops
Delta
15h 46m
KOA - MDW
3/29
Mon
1 stop
United Airlines
30h 25m
ORD - ITO
3/31
Wed
1 stop
United Airlines
28h 45m
ITO - ORD
3/9
Tue
1 stop
United Airlines
27h 35m
ORD - ITO
3/24
Wed
1 stop
United Airlines
28h 45m
ITO - ORD
3/9
Tue
1 stop
United Airlines
27h 35m
ORD - ITO
3/16
Tue
1 stop
United Airlines
23h 12m
ITO - ORD
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Recent one-way flight deals

3/3
Wed
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/2
Tue
2 stops
Multiple Airlines
17h 23m
ORD - OGG
3/1
Mon
2 stops
Multiple Airlines
16h 13m
ORD - OGG
2/22
Mon
2 stops
Multiple Airlines
17h 44m
ORD - OGG
2/21
Sun
2 stops
Multiple Airlines
16h 13m
ORD - OGG
2/24
Wed
2 stops
Multiple Airlines
25h 51m
ORD - OGG
3/17
Wed
2 stops
Multiple Airlines
23h 06m
ORD - OGG
2/16
Tue
1 stop
United Airlines
22h 20m
ORD - HNL
3/4
Thu
1 stop
American Airlines
14h 29m
ORD - OGG
2/16
Tue
2 stops
United Airlines
31h 30m
ORD - HNL
3/17
Wed
1 stop
Alaska Airlines
16h 20m
ORD - OGG
3/30
Tue
2 stops
United Airlines
24h 53m
ORD - HNL
2/25
Thu
2 stops
United Airlines
17h 21m
ORD - OGG
3/10
Wed
2 stops
American Airlines
19h 30m
ORD - KOA
2/21
Sun
2 stops
American Airlines
27h 17m
ORD - KOA
2/16
Tue
1 stop
Delta
16h 50m
ORD - LIH
3/27
Sat
1 stop
Delta
16h 31m
ORD - KOA
3/16
Tue
1 stop
Alaska Airlines
18h 30m
ORD - LIH
2/16
Tue
2 stops
Delta
17h 20m
ORD - LIH
3/13
Sat
1 stop
Alaska Airlines
32h 40m
ORD - LIH
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