$140 Find Cheap Flights from Chicago to Hawaii

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hawaii departing on 1/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Hawaii

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hawaii.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Hawaii.
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Cheap Flights from Chicago to Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu2 stops$484
Kahului
Kahului1 stop$412
Kailua-Kona
Kailua-Kona1 stop$322
Lihue
Lihue2 stops$284
Hilo
Hilo2 stops$362
Honolulu
Honolulu2 stops$484
Kahului
Kahului1 stop$412
Kailua-Kona
Kailua-Kona1 stop$322
Lihue
Lihue2 stops$284
Hilo
Hilo2 stops$362

Book Cheap Chicago to Hawaii Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hawaii that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hawaii

Tue, Feb 24 - Tue, Mar 3
Alaska Airlines Logo
8:20 am - 6:17 am
ORD
-
LIH
25h 57m2 stops
Alaska Airlines Logo
4:50 pm - 11:59 pm
LIH
-
ORD
27h 09m1 stop
$284Alaska Airlines
Mon, Feb 2 - Mon, Feb 9
Alaska Airlines Logo
3:44 pm - 1:03 pm
ORD
-
LIH
25h 19m1 stop
Alaska Airlines Logo
4:00 pm - 2:29 pm
LIH
-
ORD
18h 29m2 stops
$296Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Alaska Airlines Logo
8:20 am - 12:47 pm
ORD
-
LIH
32h 27m1 stop
Alaska Airlines Logo
4:50 pm - 11:59 pm
LIH
-
ORD
27h 09m1 stop
$297Alaska Airlines
Mon, Feb 2 - Mon, Feb 9
Alaska Airlines Logo
9:00 am - 6:17 am
ORD
-
LIH
25h 17m2 stops
Alaska Airlines Logo
6:33 pm - 2:29 pm
LIH
-
ORD
15h 56m2 stops
$302Alaska Airlines
Wed, Mar 4 - Mon, Mar 9
Delta Logo
2:20 pm - 7:34 pm
ORD
-
KOA
33h 14m1 stop
Delta Logo
8:55 pm - 1:24 pm
KOA
-
ORD
11h 29m1 stop
$346Delta
Tue, Mar 3 - Wed, Mar 11
Delta Logo
9:50 am - 6:30 pm
MDW
-
KOA
36h 40m2 stops
Delta Logo
8:55 pm - 8:50 am
KOA
-
MDW
30h 55m2 stops
$404Delta
Wed, Jan 21 - Sun, Jan 25
Southwest Logo
5:05 am - 12:50 pm
MDW
-
OGG
11h 45m1 stop
Southwest Logo
9:25 pm - 2:45 pm
OGG
-
MDW
13h 20m1 stop
$432Southwest
Tue, Mar 3 - Mon, Mar 9
Southwest Logo
6:10 am - 9:20 pm
MDW
-
KOA
19h 10m2 stops
Southwest Logo
8:25 pm - 2:50 pm
KOA
-
MDW
13h 25m1 stop
$447Southwest
Tue, Jan 13 - Mon, Jan 19
Multiple Airlines Logo
12:00 pm - 11:00 am
ORD
-
HNL
27h 00m1 stop
Multiple Airlines Logo
9:38 pm - 10:38 pm
HNL
-
ORD
45h 00m2 stops
$492Multiple Airlines
Tue, Jan 6 - Tue, Jan 13
Multiple Airlines Logo
2:03 pm - 11:00 am
MDW
-
HNL
24h 57m1 stop
Multiple Airlines Logo
9:38 pm - 11:47 am
HNL
-
MDW
34h 09m2 stops
$493Multiple Airlines
Booking Insights

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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Hawaii departing in April.

What is the cheapest Chicago to Hawaii flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Hawaii from Chicago found in the last 72 hours was to Honolulu, at $531 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 72 hours was $531.

What is the cheapest month to fly from Chicago to Hawaii?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Hawaii, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Hawaii is January, when tickets cost $641 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $906 and $903 respectively.

What’s the cheapest day of the week to fly from Chicago to Hawaii?

The average price of all round-trip flights from Chicago to Hawaii clicked on KAYAK for each day over the last 12 months.

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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Hawaii, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$140
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport to Kahului

FAQs - booking Hawaii flights

  • 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.

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Hawaii.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • 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 66% 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 $1,269.

Top tips for finding cheap flights to Hawaii

  • 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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Hawaii. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
Alaska AirlinesOverall score based on 11411 reviews
7.1Food
8.5Crew
8.1Boarding
7.8Comfort
7.0Entertainment
Airline reviews

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

8.0 ExcellentAnonymous, Dec 2025
ORD - SAN
Read more Alaska Airlines reviews

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

It was fine. It was a 30 minute flight so there was water or fruit juice and no food. Which was totally fine. The check in, gate and flight crew were all excellent.

I didn’t order food so can’t really say how it was. Overall, it was a great experience.

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use

Glad they offer free meal, & I got a complimentary drink I’d like coffee,tea, or water offered 3/4 into trip

Could not check in online. Called airline twice, thinking Hawaiian Airlines could check me in during phone call. NO. In 2nd phone call, Customer Service explained that due to “transition period” of Hawaiian Airlines/Alaska Airlines merger, I could only check in at the airport. In addition, flight to Kahului was late at arrival gate; I made connection to Lihue but my bag did not, so I had to return to Lihue airport a couple hours after my arrival to retrieve the bag.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

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.

We loved the steward on the plane. He made the night enjoyable

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

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.

Everything you need to know for your flight from Chicago to Hawaii

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Hawaii. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.