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Find cheap flights from Chicago to Hawaii from $179

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 5/29. 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 6/6
Thu 6/13

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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$445
Kahului
Kahului1 stop$428
Kailua-Kona
Kailua-Kona1 stop$422
Lihue
Lihue2 stops$427
Hilo
Hilo2 stops$869

Good to know

Low season

April

High season

December

Cheapest flight

$179
Best time to beat the crowds with an average 22% 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 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 11% 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 1538 reviews
8.0Entertainment
7.9Food
8.6Crew
8.4Boarding
8.2Comfort
Airline reviews

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.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

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.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

t and I Flight crew did excellent job taking care of us and feeding us and staying professional. The boarding was delayed by an hour and then extra security measures were taken. No real explanation except for they said it was more of a maintenance dey

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.

Plane was so old it had cigarette butt trays in the seat

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

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.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Hawaii

Recent round-trip flight deals

8/17Sat
1 stopAlaska Airlines
30h 59mORD-KOA
8/23Fri
1 stopAlaska Airlines
10h 50mKOA-ORD
$422
8/19Mon
1 stopDelta
14h 44mORD-KOA
8/26Mon
2 stopsDelta
15h 14mKOA-ORD
$427
8/14Wed
2 stopsDelta
16h 22mORD-LIH
8/22Thu
1 stopDelta
11h 35mLIH-ORD
$427
8/10Sat
1 stopUnited Airlines
13h 50mORD-OGG
8/19Mon
1 stopUnited Airlines
10h 53mOGG-ORD
$428
8/19Mon
2 stopsDelta
17h 25mORD-KOA
8/26Mon
2 stopsDelta
15h 14mKOA-ORD
$432
9/10Tue
1 stopAmerican Airlines
13h 09mORD-OGG
9/17Tue
1 stopAmerican Airlines
11h 30mOGG-ORD
$437
9/2Mon
1 stopAmerican Airlines
11h 06mORD-LIH
9/9Mon
1 stopAmerican Airlines
11h 40mLIH-ORD
$441
8/22Thu
1 stopUnited Airlines
12h 39mORD-OGG
8/31Sat
1 stopUnited Airlines
10h 53mOGG-ORD
$448
5/16Thu
2 stops
21h 44mORD-HNL
6/4Tue
2 stops
18h 11mHNL-ORD
$500
5/16Thu
2 stops
21h 44mORD-HNL
6/4Tue
3 stops
31h 34mHNL-ORD
$510

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Recent one-way flight deals

5/29Wed
1 stopAmerican Airlines
10h 46mORD-OGG
$179
8/31Sat
1 stopDelta
14h 44mORD-KOA
$211
8/31Sat
2 stopsDelta
17h 25mORD-KOA
$216
8/31Sat
2 stopsDelta
13h 50mMDW-KOA
$216
8/24Sat
1 stopAlaska Airlines
33h 00mORD-KOA
$217
10/2Wed
1 stopAmerican Airlines
12h 51mORD-HNL
$222
10/27Sun
1 stopUnited Airlines
15h 23mORD-HNL
$266
5/30Thu
1 stopAlaska Airlines
20h 19mORD-HNL
$269
8/24Sat
1 stopUnited Airlines
11h 39mORD-KOA
$281
7/28Sun
3 stopsWestJet
31h 58mORD-OGG
$404

Search by stops

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Last minute flights from Chicago to Hawaii

Last minute flight, train and bus deals

5/9Thu
multi-stopAmerican Airlines
11h 07mORD-LIH
5/12Sun
multi-stopAmerican Airlines
13h 00mLIH-ORD
$522
5/9Thu
multi-stopAmerican Airlines
15h 29mORD-LIH
5/12Sun
multi-stopAmerican Airlines
13h 00mLIH-ORD
$525
5/7Tue
multi-stopDelta
13h 38mORD-HNL
5/9Thu
multi-stopDelta
11h 35mHNL-ORD
$562
5/7Tue
multi-stopDelta
16h 30mORD-KOA
5/9Thu
multi-stopDelta
10h 54mKOA-ORD
$562
5/8Wed
multi-stopAlaska Airlines
18h 07mORD-HNL
5/21Tue
multi-stopAlaska Airlines
11h 54mHNL-ORD
$571
5/11Sat
multi-stopAlaska Airlines
31h 31mORD-HNL
5/17Fri
multi-stopAlaska Airlines
11h 54mHNL-ORD
$580
5/10Fri
multi-stopUnited Airlines
12h 53mORD-OGG
5/17Fri
multi-stopUnited Airlines
16h 40mOGG-ORD
$731
5/10Fri
multi-stopUnited Airlines
13h 43mORD-OGG
5/17Fri
multi-stopUnited Airlines
14h 12mOGG-ORD
$786
5/9Thu
multi-stop
24h 36mORD-LIH
5/23Thu
multi-stop
17h 15mLIH-ORD
$967
5/7Tue
multi-stop
11h 55mORD-HNL
5/13Mon
nonstop
8h 11mHNL-ORD
$1,340

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Flights to Hawaii

Return flight deals:

Hawaii - Chicago

Cabin classes:

$2,171
$3,223
$1,330
$895