
Cheap Flights from Chicago to Hawaii
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Chicago to Hawaii Plane Tickets
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KAYAK's insights & trends for Chicago to Hawaii flights
Get data-powered insights and trends into flights from Chicago to Hawaii to help you find the cheapest flights, the best time to fly and much more.
How much is a round-trip flight from Chicago to Hawaii?
Flight prices are below average for this route right now.
Flights to Hawaii from Chicago usually cost between $678 and $1,116 in January.The lowest price found in the past 5 days was $558 on Multiple Airlines (Jan 6-Jan 13).
What is the cheapest Chicago to Hawaii flight route?
The cheapest ticket to Hawaii from Chicago found in the last 5 days was to Honolulu, at $546 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Honolulu (HNL), and the cheapest round-trip airline ticket found on this route in the last 5 days was $546.
What is the cheapest time of day to fly to Hawaii?
The cheapest time of day to fly to Hawaii is generally in the morning, when round-trip flights cost $883 on average. The most expensive time of day to fly to Hawaii is generally in the morning, which is peak travel time and where the average cost of a ticket is $883.
Can I save money by flying with a layover from Chicago to Hawaii?
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $776 on average.
What is the cheapest month to fly from Chicago to Hawaii?
The cheapest month for flights from Chicago to Hawaii is February, when tickets cost $628 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $938 and $933 respectively.
What’s the cheapest day of the week to fly from Chicago to Hawaii?
Your flight ticket price will generally be cheaper if you fly to Hawaii on a Tuesday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Saturdays for better deals.
How far in advance should I book a flight from Chicago to Hawaii?
To get a below average price on the flight from Chicago to Hawaii, you should book around 4 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.
Which airlines fly non-stop between Chicago and Hawaii?
There are 3 airlines that fly nonstop from Chicago to Hawaii. They are: American Airlines, Alaska Airlines and United Airlines. The cheapest price of all airlines flying this route was found with United Airlines at $394 for a round-trip flight to Honolulu (HNL). On average, Alaska Airlines offers the best prices for nonstop flights between Chicago and Hawaii.
Which airlines provide the cheapest flights from Chicago to Hawaii?
In the past 5 days, the cheapest round-trip tickets from Chicago to Hawaii were found on United Airlines ($424) and Delta ($430).
How long does a flight from Chicago to Hawaii take?
The duration of a flight to Hawaii depends on your arrival airport. The shortest routes to Hawaii from Chicago are to Kahului, which takes 10h 05m, Honolulu, which takes 10h 05m, and Kailua-Kona, which takes 10h 15m.
Which cabin class options are there for flights between Chicago and Hawaii?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago to Hawaii?
The earliest flight from Chicago to Hawaii departs at 9:15 am, landing in Honolulu at 2:27 pm.
What’s the latest departure time from Chicago to Hawaii?
If you prefer to fly at night, the latest flight from Chicago to Hawaii jets off at 10:00 am and lands in Honolulu at 2:06 pm.
Good to know
Low season | September |
|---|---|
High season | March |
Cheapest flight | $212 |
FAQs - booking Hawaii flights
Top tips for finding cheap flights to Hawaii
Reviews of the top 5 airlines serving from Chicago to Hawaii
I paid extra to choose a seat. When arriving at the gate after a very stressful check in at the airport, realized did not get the chosen seat that I PAID for. When I called the airline I was told I did not pay to choose a seat and could not be refunded, but I DID pay extra to choose a seat. And of course, got stuck in a MIDDLE seat. Since the seats are now crammed together, this is especially uncomfortable. The check in for baggage was ridiculous, it was a mile long and the kiosk to check in for the flight was very confusing. We finally sought out help and a very rude representative quickly went through the kiosk and printed a boarding pass that did not provide the PAID for chosen seat. Didn't get to get on the return flight because the flight coming in was delayed several hours, missed the flight by 3 minutes!!!!!!! You really can't hold the door for 3 minutes for a passenger you KNOW you are waiting for??? What stress and had to wait 4 MORE HOURS to get a flight home because you could not keep the door open 3 minutes. 3 minutes. Had only 20 minutes to get from flight to connecting flight and was accused of taking too long to get from gate to gate in Chicago. Flights were delayed all day long coming in and going out, you would think you could wait 3 minutes to allow passengers to get to the connecting flights. HUGE inconvenience, stressful and makes for a really LONG day when the flight leaving Des Moines to Chicago was horribly delayed, already had a horrible experience and missed the connecting flight by 3 minutes. 3 minutes. Airplane was still there, the door closed, why on earth is it such a huge deal to wait a few minutes when flights were already delayed ALL DAY LONG and why is it such a huge deal to REOPEN the door to let another passenger on??!! I used to like Alaska Airlines. I just plain hate flying in general now. The airlines have 0 (zero)care about the people buying tickets and making travel plans and how stressful flying is now. Zero care.
I paid extra to choose a seat. When arriving at the gate after a very stressful check in at the airport, realized did not get the chosen seat that I PAID for. When I called the airline I was told I did not pay to choose a seat and could not be refunded, but I DID pay extra to choose a seat. And of course, got stuck in a MIDDLE seat. Since the seats are now crammed together, this is especially uncomfortable. The check in for baggage was ridiculous, it was a mile long and the kiosk to check in for the flight was very confusing. We finally sought out help and a very rude representative quickly went through the kiosk and printed a boarding pass that did not provide the PAID for chosen seat. Didn't get to get on the return flight because the flight coming in was delayed several hours, missed the flight by 3 minutes!!!!!!! You really can't hold the door for 3 minutes for a passenger you KNOW you are waiting for??? What stress and had to wait 4 MORE HOURS to get a flight home because you could not keep the door open 3 minutes. 3 minutes. Had only 20 minutes to get from flight to connecting flight and was accused of taking too long to get from gate to gate in Chicago. Flights were delayed all day long coming in and going out, you would think you could wait 3 minutes to allow passengers to get to the connecting flights. HUGE inconvenience, stressful and makes for a really LONG day when the flight leaving Des Moines to Chicago was horribly delayed, already had a horrible experience and missed the connecting flight by 3 minutes. 3 minutes. Airplane was still there, the door closed, why on earth is it such a huge deal to wait a few minutes when flights were already delayed ALL DAY LONG and why is it such a huge deal to REOPEN the door to let another passenger on??!! I used to like Alaska Airlines. I just plain hate flying in general now. The airlines have 0 (zero)care about the people buying tickets and making travel plans and how stressful flying is now. Zero care.
They overbooked the flight! Or they said it was over weight, very unnerving as flying is a gamble anyway. They were waiting for six passengers to give up their seats, before they would board the flight, they were offering $1100. I’m guessing towards the purchase of the next ticket which I would never purposely fly with American Airlines. It was just the only flight available with what I needed. American Airlines is the top two worst airlines to fly with. And then after waiting an hour and four minute delay departing they ended up seating the people that they had asked to give up their seats anyway turns out they were not overweight after all. So all of that in a delayed flight and a delayed landing in Des Moines for nothing American Airlines is in competition with United Airlines for the worst airline to fly with.
The seat was comfortable, but I paid for upgraded seats and they did not state that there was no outlets for devices.
Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.
Thanks for all you do to keep us safe and on time!
I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.
No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.
I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.
Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.
The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.
Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.
Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.
A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack
I like the staff members they were super nice and helpful very sweet people :)
Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.
Overall good, just screaming kids in the area the whole flight.
OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.
The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.
I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
I'm 6' 2" and even in economy plenty of leg room
Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.
THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY
The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.
The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.
Very easy to use and convenient, you can perform any action within the same portal
Okay considering we had weather delays which the Pilot notified us of immediately!
The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.
Everything could have benn better. Short fly, no food, no entertainment and no wifi.
Stop changing gates. Stop cancelling flights Stop moving my seat.
Price was crazy watch it if you Chan he your flight
On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.
Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s
No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.
Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late
Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.
Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.
Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.
It was a good experience, unfortunately my checked baggages were come late and not arrived on time.
Everything was good, hard to really comfortable on a flight that long.
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.
The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.
Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.
The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.
Flight was delayed and so much of inconvenience related to the gate change.
Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes