$212 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 9/1. 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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Flight Deals

Cheap Flights from Chicago to Hawaii

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Honolulu
Honolulu2 stops$616
Kahului
Kahului1 stop$525
Kailua-Kona
Kailua-Kona1 stop$491
Lihue
Lihue1 stop$424
Hilo
Hilo2 stops$565
Honolulu
Honolulu2 stops$616
Kahului
Kahului1 stop$525
Kailua-Kona
Kailua-Kona1 stop$491
Lihue
Lihue1 stop$424
Hilo
Hilo2 stops$565

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

Mon, Sep 21 - Tue, Sep 29
Delta Logo
12:40 pm - 7:20 pm
ORD
-
LIH
11h 40m
1 stop
Delta Logo
9:45 pm - 1:30 pm
LIH
-
ORD
10h 45m
1 stop
$424Delta
Tue, Jun 2 - Wed, Jun 10
United Airlines Logo
7:05 am - 3:37 pm
ORD
-
LIH
13h 32m
1 stop
United Airlines Logo
1:01 pm - 4:51 am
LIH
-
ORD
10h 50m
1 stop
$428United Airlines
Tue, Aug 18 - Thu, Aug 27
Delta Logo
7:45 am - 7:03 pm
ORD
-
LIH
16h 18m
2 stops
Delta Logo
9:55 pm - 4:43 pm
LIH
-
ORD
13h 48m
1 stop
$430Delta
Sun, Sep 13 - Fri, Sep 25
Multiple Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
$491Multiple Airlines
Mon, Sep 7 - Thu, Sep 17
Multiple Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
$492Multiple Airlines
Tue, Aug 25 - Thu, Aug 27
Alaska Airlines Logo
2:18 pm - 2:48 pm
ORD
-
KOA
29h 30m
1 stop
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$493Alaska Airlines
Tue, Aug 25 - Thu, Aug 27
Alaska Airlines Logo
6:01 am - 2:51 pm
ORD
-
KOA
13h 50m
1 stop
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$494Alaska Airlines
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$494Southwest
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
8:35 pm - 3:15 pm
KOA
-
MDW
13h 40m
2 stops
$500Southwest
Wed, Nov 4 - Tue, Nov 10
American Airlines Logo
1:49 pm - 9:59 pm
ORD
-
HNL
12h 10m
1 stop
American Airlines Logo
7:00 pm - 7:10 am
HNL
-
ORD
8h 10mnonstop
$617American 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 September.

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 7 days was to Kahului, at $636 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 7 days was $678.

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

The average price for all round-trip flights from Chicago to Hawaii depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Hawaii is generally in the morning, when round-trip flights cost $898 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 $898.

Can I save money by flying with a layover from Chicago to Hawaii?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $877 on average.

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 February, when tickets cost $541 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $1,230 and $979 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$212
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Chicago O'Hare Airport to Lihue

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.

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.
7.9
Alaska AirlinesOverall score based on 12396 reviews
7.0Food
8.1Boarding
8.5Crew
7.8Comfort
7.0Entertainment
Airline reviews

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

10.0 ExcellentSummer, May 2026
LAX - OGG
Read more Alaska Airlines reviews

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

The crew seem untrained and uncertain no one ever checked up on us in our first class cabin. I had to ask for water four times and the lady kept saying she was busy when they weren't really doing anything. Had to walk to the back of the plane to get water for myself. Crew seem new and unexperience. You can tell this by the fumbling they kept making trying to fight. (I miss Hawaiian air.)

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

You can standby to get on earlier flight if the seat is open.

Thanks for all you do to keep us safe and on time!

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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.