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Find cheap flights from Chicago to Hawaii from $209

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 7/30. 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
0 bags
Thu 6/27
Thu 7/4

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Best Hawaii Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Honolulu
Honolulu1 stop$421
Kahului
Kahului1 stop$375
Kailua-Kona
Kailua-Kona1 stop$421
Lihue
Lihue1 stop$422
Hilo
Hilo2 stops$769

Good to know

Low season

April

High season

July

Cheapest flight

$209
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 17% 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 to Hawaii from Chicago 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 to Hawaii with an airline and back to Chicago 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 to Hawaii from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Hawaii

  • Morning departure is around 10% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.3
EVA AirOverall score based on 1501 reviews
8.6Crew
7.9Food
8.0Entertainment
8.4Boarding
8.2Comfort
Airline reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

8.0 ExcellentYue, May 2024IAH - TPE
Read more about EVA Air reviews

Their announcement was not quite clear in Chinese. The rest is pretty good.

The hygiene of the bathrooms were terrible. Urine smells leaked out into the cabin and the seats were really tight, even for a petite woman like myself. Flight attendants did not go through the cabin enough to offer refreshments.

I was expecting that movie selection and food would have been better. Everything else was great.

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

The flight was on time and nice as always for me with spirit but the cabin crew were not good. They left the lights on on a red eye for the entire flight.

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Book cheap flights from Chicago to Hawaii

Recent round-trip flight deals

9/10Tue
1 stopAlaska Airlines
21h 02mORD-OGG
9/17Tue
1 stopAlaska Airlines
19h 08mOGG-ORD
$375
9/10Tue
1 stopAmerican Airlines
13h 55mORD-OGG
9/17Tue
1 stopAmerican Airlines
13h 12mOGG-ORD
$376
8/20Tue
1 stopAlaska Airlines
32h 52mORD-OGG
8/27Tue
1 stopAlaska Airlines
19h 08mOGG-ORD
$380
9/10Tue
1 stopDelta
14h 53mORD-OGG
9/17Tue
2 stopsDelta
13h 46mOGG-ORD
$381
8/20Tue
1 stopAmerican Airlines
13h 52mORD-OGG
8/27Tue
1 stopAmerican Airlines
12h 04mOGG-ORD
$386
9/19Thu
1 stopDelta
14h 53mORD-OGG
9/24Tue
1 stopDelta
10h 53mOGG-ORD
$392
8/16Fri
1 stopUnited Airlines
14h 03mORD-OGG
8/23Fri
1 stopUnited Airlines
11h 43mOGG-ORD
$402
8/7Wed
1 stopUnited Airlines
11h 38mORD-OGG
8/14Wed
1 stopUnited Airlines
10h 37mOGG-ORD
$418
7/9Tue
3 stops
33h 47mORD-LIH
7/16Tue
2 stops
16h 00mLIH-ORD
$713
6/12Wed
1 stop
18h 33mORD-LIH
6/19Wed
3 stops
19h 00mLIH-ORD
$716

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Recent one-way flight deals

7/30Tue
1 stopDelta
15h 03mORD-OGG
$209
8/20Tue
1 stopAmerican Airlines
12h 15mORD-HNL
$211
7/24Wed
1 stopAlaska Airlines
19h 07mORD-KOA
$211
9/19Thu
1 stopAlaska Airlines
19h 45mORD-LIH
$211
8/31Sat
2 stopsDelta
13h 26mORD-HNL
$216
5/31Fri
2 stopsAmerican Airlines
14h 27mORD-OGG
$236
11/19Tue
1 stopUnited Airlines
13h 49mORD-LIH
$281
8/24Sat
3 stopsWestJet
33h 03mORD-HNL
$297
7/1Mon
1 stopUnited Airlines
12h 12mORD-KOA
$331
5/31Fri
3 stopsWestJet
32h 06mORD-OGG
$383

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Last minute flights from Chicago to Hawaii

Last minute flight, train and bus deals

5/29Wed
multi-stopAlaska Airlines
23h 31mORD-OGG
6/5Wed
multi-stopAlaska Airlines
24h 58mOGG-ORD
$520
6/1Sat
multi-stopUnited Airlines
12h 09mORD-LIH
6/9Sun
multi-stopUnited Airlines
13h 15mLIH-ORD
$523
5/29Wed
multi-stopAlaska Airlines
17h 02mORD-OGG
6/8Sat
multi-stopAlaska Airlines
26h 58mOGG-ORD
$550
6/2Sun
multi-stopAlaska Airlines
19h 54mORD-LIH
6/5Wed
multi-stopAlaska Airlines
11h 26mLIH-ORD
$551
6/2Sun
multi-stopDelta
15h 59mORD-OGG
6/6Thu
multi-stopDelta
14h 30mOGG-ORD
$562
5/31Fri
multi-stopAmerican Airlines
13h 54mORD-HNL
6/3Mon
multi-stopAmerican Airlines
11h 28mHNL-ORD
$566
5/31Fri
multi-stopDelta
12h 02mORD-HNL
6/6Thu
multi-stopDelta
15h 35mHNL-ORD
$575
6/2Sun
multi-stopAlaska Airlines
19h 54mORD-LIH
6/7Fri
multi-stopAlaska Airlines
29h 35mLIH-ORD
$579
5/31Fri
multi-stopAlaska Airlines
22h 59mORD-HNL
6/9Sun
multi-stopAlaska Airlines
28h 33mHNL-ORD
$580
5/31Fri
multi-stopAmerican Airlines
13h 54mORD-HNL
6/2Sun
multi-stopAmerican Airlines
13h 05mHNL-ORD
$610

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Flights to Hawaii

Return flight deals:

Hawaii - Chicago

Cabin classes:

$2,171
$3,325
$1,330
$743