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Cheap Flights from Chicago to Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Honolulu
Honolulu2 stops$556
Kahului
Kahului2 stops$589
Kailua-Kona
Kailua-Kona1 stop$575
Lihue
Lihue1 stop$417
Hilo
Hilo2 stops$583
Honolulu
Honolulu2 stops$556
Kahului
Kahului2 stops$589
Kailua-Kona
Kailua-Kona1 stop$575
Lihue
Lihue1 stop$417
Hilo
Hilo2 stops$583
Booking Insights

Price, demand and travel trends for Chicago to Hawaii flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago to Hawaii recently?

The cheapest fare from Chicago to Hawaii in the last week was $417 round-trip, to Lihue (LIH).

How do fares into airports in Hawaii compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Hawaii from Chicago are:

• Lihue (LIH) (avg. price $586)
• Kona Intl (KOA) (avg. price $732)
• Honolulu (HNL) (avg. price $764)

Are flights from Chicago to Hawaii cheaper or more expensive than last year?

Fares from Chicago to Hawaii are about 6% higher than they were in November last year, averaging $832 round-trip.

What's the cheapest month to fly from Chicago to Hawaii?

February is typically the cheapest month to fly from Chicago to Hawaii, with round-trip fares averaging $624. December and June are usually the most expensive, averaging $946 and $886, respectively.

How do fares from Chicago to Hawaii vary by day of the week?

On average, Wednesday is the cheapest day to fly from Chicago to Hawaii and Saturday is the most expensive. Looking at the past 12 months of KAYAK data, it's 39% more expensive to fly on a Saturday compared to Wednesday.

What's the best time of day to fly from Chicago to Hawaii?

It's cheapest to fly to Hawaii at night with average prices of $657. The morning is the most expensive time to fly, with average prices of $793.

What's the best time to book a flight from Chicago to Hawaii?

Book your flights 5 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 24% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago to Hawaii flights

Low season

October

Cheapest flight

$212
Beat the crowds with an average 33% drop in travelers.
The most popular month to fly with an average 46% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Lihue

Your Chicago to Hawaii flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Hawaii?

    Yes. Fares from Chicago to Hawaii are low right now. As a rule of thumb, a round-trip under $580 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago to Hawaii?

    Over the past 12 months, round-trip fares from Chicago to Hawaii have typically cost between $580 and $992.

  • What are the main airports serving Hawaii?

    There are 12 airports in Hawaii. 45% of KAYAK users choose Honolulu (HNL) as their arrival airport, while 26% choose Kahului (OGG).

  • Which airlines fly nonstop from Chicago to Hawaii?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Which destinations in Hawaii can I fly nonstop from Chicago?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago to 3 destinations in Hawaii. The most popular among KAYAK travelers are Honolulu, Kahului and Kailua-Kona.

  • Is it cheaper to fly with a layover from Chicago to Hawaii?

    Yes, nonstop flights from Chicago to Hawaii average $916 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Atlanta Hartsfield-Jackson (ATL) (avg. price $499)
    • Oakland (OAK) (avg. price $579)
    • San Jose (SJC) (avg. price $608)

  • How long is a flight from Chicago to Hawaii?

    Nonstop flights from Chicago to Hawaii take 9h 19m on average. The fastest scheduled flight takes 8h 46m, flying into Kahului (OGG).

  • Which cabin classes are available from Chicago to Hawaii?

    On flights from Chicago to Hawaii you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks around Hawaii?

    Hawaii is home to many popular sights. KAYAK travelers' favorites include:

    • Waikiki Beach
    • Hawaii Convention Center
    • International Market Place
    • Kuhio Beach Park

  • What are the earliest and latest flights from Chicago to Hawaii?

    The earliest nonstop flight from Chicago to Hawaii departs at 9:15 am and the latest leaves at 12:45 pm. Nonstop flights take about 9h 19m.

  • Does Daniel K, Inouye International Airport (HNL) provide accessibility services?

    Yes. HNL is an accessible airport. Passengers with limited mobility will have access to a wheelchair (via early arrangements through their preferred airline), accessible washrooms, parking, transportation, and fast-track services at the Airport. Elevators and ramps available in every terminal provide step-free access through the Airport. Persons with visual impairments will access free Aira services, while passengers with hearing impairments have TDD telephones and visual paging.

  • What are the passport and visa requirements for flying to Hawaii from Chicago?

    American citizens flying to Hawaii from Chicago don’t need to have a visa or passport. Nevertheless, you’ll need to have a valid driver’s license from the state you live in. If you don’t possess a driver’s license, you’ll need to have a valid identification card from your home state. Your identification card or driver’s license will need to be valid for the stretch of your journey or else you’ll have to renew either before heading on your trip to Hawaii.

  • What are the most common layover cities for flights connecting to Hawaii from Chicago?

    Unfortunately, direct flights to Hawaii from Chicago are not available. Flights to Hawaii from Chicago are rather long therefore, will involve at least one layover stop. Yet, some flights from Chicago to Hawaii will have two stopovers en route. The layover stop will depend on which airline you're flying with and which destination you arrive at in Hawaii. Los Angeles, Seattle, and San Francisco are the route’s popular layover cities.

  • Are there pet relief areas at Chicago O'Hare International Airport (ORD)?

    Yes. ORD welcomes pets and service animals at the airport. O'Hare Airport has indoor and outdoor pet relief areas close to the terminals, and they are available round the clock to travelers flying with their pets or service animals. At ORD, you'll find the animal relief areas in Terminal 1, Terminal 5, and Terminal 2 outside the arrivals level by gates 1A, 5B, and 2A, respectively. Indoor pet relief areas are in Terminal 1 Concourse C close to Gate C10, the Rotunda between Terminals 2 and 3, and Terminal 3 main hall.

Your guide to booking Chicago to Hawaii flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 5 weeks before your trip. KAYAK data shows fares in this window are around 24% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in February to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Wednesday to get the cheapest fares. Avoid Saturday flights, which are about 39% more expensive.
  • If you're watching your budget, fly into Lihue (LIH) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Honolulu, the most popular destination in Hawaii. From there, it's easy to continue on to other popular spots such as Kahului, Kailua-Kona and Lihue.
  • Time or money? If speed matters most, fly from Chicago to Kahului (OGG). If you're after the lowest fares, Lihue (LIH) is usually your best bet.
  • Chicago Midway International Airport (MDW) is one of the main airports serving the metropolis of Chicago.  MDW is a base for passenger airlines such as Southwest Airlines and Frontier Airlines, which facilitate transfers from Chicago to Hawaii.
  • MDW provides nursing stations for mothers to breast or bottle-feed their babies or pump milk while on the go. MDW’s nursing amenity has sinks, a wash area, comfortable chairs, a changing counter, electrical outlets, and a wall-mounted TV. At MDW the mothers’ room is on Concourse C adjacent to the Yoga Room. Moreover, MDW has Mamava lactation pods on Concourse A by Gate A5.
  • Chicago O’Hare International Airport (ORD) is one of the primary airports serving the city of Chicago. The Airport is a hub for the passenger airlines - American Airlines and United Airlines both facilitating flights to Hawaii from Chicago.
  • If you’re searching for a spot to relax and meditate before your flight to Hawaii, MDW has a yoga room. Besides, supplying complimentary yoga mats, the yoga room offers an area to place your personal effects. The yoga room is located on Concourse C adjacent to the mothers’ nursing room.
  • Daniel K. Inouye International Airport (HNL) is one of the primary airports serving the State of Hawaii situated in Oahu. HNL is the main hub for Mokulele Airlines and Hawaii Airlines, which facilitate transfers to Hawaii from Chicago.

Reviews of the top 5 airlines serving from Chicago to Hawaii

 
Need help choosing which airline to fly with from Chicago 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
SouthwestOverall score based on 4219 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

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.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

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.

Great flight with great crew. I like that they came around to serve our strings twice during our four-hour flight.

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.

No beverage/snack service without any explanation or reason. Late boarding and delayed flight.

The cabin and bathroom experience was poor as the cabin and bathroom were dirty and showed signs of an older plane that had not been updated for Customer’s, comfort and health. There was gum on my seat when I arrived and dirt spots around the fan and light controls. The flight was almost entirely full, so there was no way I could be moved from my seat. Th bathroom had the peeling paint.

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.

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

Everything was good, hard to really comfortable on a flight that long.

All good. Flight crew was super friendly at the end of a long day

The food in first class has taken a big downturn

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

I have posted the comments in the first flight leg.

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.

More options for your flight from Chicago to Hawaii

Complete your trip to Hawaii with a hotel stay or car rental