$179 Find Cheap Flights from Illinois to Hawaii

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Low seasonSeptember
Cheapest flight$179
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Chicago O'Hare Airport to Kahului

FAQs for booking flights from Illinois to Hawaii

  • How does KAYAK find such low prices on flights from Illinois to Hawaii?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Hawaii.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Hawaii?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Hawaii?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Illinois to Hawaii with an airline and back with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Illinois to Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Hawaii?

    There are 11 airports in Hawaii. The busiest airport is Honolulu Airport (HNL), with 51% of all flights arriving there.

  • Which is the cheapest airport to fly into in Hawaii?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Hawaii is Honolulu Airport (HNL), with an average flight price of $502.

  • What is the cheapest day to fly to Hawaii?

    Based on KAYAK data, the cheapest day to fly to Hawaii is Thursday where round-trip tickets can be as cheap as $1,047. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $1,125 on average.

  • What is the cheapest time of day to fly to Hawaii?

    The cheapest time of day to fly to Hawaii is generally in the evening, when round-trip flights cost $631 on average. Morning departures are around 70% more expensive than evening flights, on average. The most expensive time of day to fly to Hawaii is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $1,254.

  • What is the cheapest flight to Hawaii?

    The cheapest ticket to Hawaii from Illinois found in the last 72 hours was to Honolulu, at $531 round-trip. The most popular route is Chicago O'Hare Intl Airport (ORD) to Honolulu (HNL) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $531.

  • What is the cheapest month to fly from Illinois to Hawaii?

    The cheapest month for flights from Illinois to Hawaii is January, when tickets cost $572 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $1,364 and $1,263 respectively.

  • How far in advance should I book a flight from Illinois to Hawaii?

    To get a below average price on the flight from Illinois to Hawaii, you should book around 4 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

  • How many cities have direct flights to Hawaii?

    From Illinois, there are direct flights to Hawaii from 1 city. This city is Chicago and there are 15 direct flights each week.

  • How many direct flights to Hawaii are there each day?

    There are around 3 direct flights from within Illinois to Hawaii every day. All flights depart in the morning.

  • How many direct flights to Hawaii are there each week?

    Each week there are around 15 direct flights from within Illinois to Hawaii. The most common day for departures is Saturday, with 20% of flights taking off on this day.

  • How long is the flight to Hawaii?

    An average nonstop flight from Illinois to Hawaii takes 17h 46m, covering a distance of 4152 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Kahului (OGG) with an average flight time of 8h 48m.

  • How many long-haul flights are there to Hawaii each week?

    There are not any medium-haul (3-6 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Hawaii. Instead, there are 15 long-haul flights (6-12 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Hawaii?

    Based on KAYAK flight searches, the most popular destination is Honolulu (57% of total searches to Hawaii). The next most popular destinations are Kahului (24%) and Lihue (9%). Searches for flights to Kailua-Kona (8%), to Hilo (2%) and to Kapalua (0%) are also popular.

Reviews of the top 5 airlines serving from Illinois to Hawaii

 
Need help choosing which airline to fly with from Illinois to Hawaii? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 11100 reviews
7.8Comfort
7.0Entertainment
8.1Boarding
7.1Food
8.5Crew
Airline reviews

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

2.0 MediocreAnonymous, Oct 2025PDX - HNL
Read more Alaska Airlines reviews

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

I liked that internet connection while in flight was available.👍

My experience from Lihue Airport was the “Flight Experience from Hell!” First, I was pulled aside by the Lihue TSA and searched thoroughly! Not once, but twice I was molested by 5 different TSA agents using some sort of smear cloth testing to see if I had been exposed to something dangerous! I can’t tell you what because they never gave me an explanation by the end of a near delaying incident of boarding my plane. More importantly, I was generously provided an airport wheel chair and personal porter because of my health condition. TSA even took your wheelchair apart! What’s up with that? I’m near 75, caucasian, never been arrested for anything, don’t do drugs or alcohol, and patiently and politely abided to their instructions for a full damn 20 minutes! Awful and humiliating experience especially when two different agents literally groped my testicles and crack of my butt! Then they lost the cap to my inhaler. When I got to my destination, a whole bottle of prescribed pills were emptied because of them not tightening the cap back on! Total BS and unprofessional by the lot of them! The short flight to my connecting flight to the mainland on Maui fortunately was uneventful. However the Hawaiian aircraft to San Jose was one of the worst flights I’ve ever experienced without crashing. I believe it was a 330 Neo. May I ask, why did you put three more rows of seats in the damn plane since I last flew on a Hawaiian aircraft? I had absolutely NO legroom compared to the last time I flew with you. And I’ve done a few Hawaii/mainland trips, even a RT to New Zealand before. Then, the icing on the cake was a couple with a one year old baby that literally cried and screamed for all but 15 minutes of the 5 hour flight to San Jose! Further, I couldn’t move my seat back even a millimeter because a car seat was placed from their window seat to the back of my seat! My Hawaiian flight was a freaking nightmare and fortunately will be flying back to Lihue direct with Alaska!

The pilot performed the smoothest landing I’ve ever experienced. What a light touch. And I’m an avid traveler!

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

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

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

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

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

I needed more space to sleep on an overnight flight.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

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

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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

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

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

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

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

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

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

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

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

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