HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$236+ Cheap flights from Hawaii to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hawaii to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Hawaii to Chicago

Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$479
(American Airlines)

One-way from

$236
(Alaska Airlines)

Popular in

July

Cheapest in

October

Average price

$699

Good round-trip deal

$506 or less

Good one-way deal

$310 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From Hawaii to Chicago (CHI)
Search Deals
One-way flight from Hawaii to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Hawaii to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Hawaii to Chicago (CHI).
Search Deals

Find flight deals from Hawaii to Chicago

Cheapest flights from Hawaii to Chicago
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/12:12 pmLIH - ORD
1 stop10h 54mAmerican Airlines
Mon 5/57:13 pmORD - LIH
1 stop22h 19mAmerican Airlines
Deal found 3/31$479
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/56:00 amLIH - ORD
2 stops12h 59mAlaska Airlines
Wed 5/79:00 amORD - LIH
1 stop17h 32mAlaska Airlines
Deal found 3/31$487
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1510:00 pmLIH - ORD
2 stops15h 05mDelta
Sat 4/197:50 amORD - LIH
1 stop15h 54mDelta
Deal found 3/31$488
This Alaska Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/209:46 pmOGG - ORD
1 stop21h 10mAlaska Airlines
Tue 5/277:59 pmORD - OGG
1 stop20h 11mAlaska Airlines
Deal found 4/1$496
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2911:45 pmHNL - ORD
1 stop25h 20mAlaska Airlines
Tue 5/66:58 pmORD - HNL
1 stop19h 42mAlaska Airlines
Deal found 3/31$519
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1512:49 pmLIH - ORD
1 stop11h 19mUnited Airlines
Sat 4/1910:44 amORD - LIH
1 stop13h 52mUnited Airlines
Deal found 3/31$530
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:35 amHNL - MDW
2 stops17h 55mSouthwest
Thu 9/259:10 pmMDW - HNL
1 stop18h 10mSouthwest
Deal found 3/31$556
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:40 pmHNL - ORD
1 stop13h 41mDelta
Mon 4/286:45 amORD - HNL
1 stop12h 25mDelta
Deal found 3/31$559
This Alaska Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/67:00 pmKOA - ORD
2 stops17h 00mAlaska Airlines
Fri 5/96:58 pmORD - KOA
2 stops23h 17mAlaska Airlines
Deal found 3/31$563
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/151:45 pmHNL - ORD
1 stop10h 29mAmerican Airlines
Tue 4/226:00 amORD - HNL
1 stop13h 48mAmerican Airlines
Deal found 3/31$563
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:40 pmHNL - MDW
1 stop13h 00mDelta
Mon 4/2810:20 amMDW - HNL
2 stops15h 21mDelta
Deal found 3/31$564
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/228:20 pmKOA - ORD
2 stops17h 38mDelta
Wed 4/307:50 amORD - KOA
1 stop14h 49mDelta
Deal found 3/31$573

Cheapflights Fare Finder

Customize your flight search to find flights from Hawaii to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2025.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.

Fly from

Hawaii

Fly to

Chicago

Route

Depart

Return

Price

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 5/1

2:12 pm-6:06 am

1 stop10h 54m

Chicago O'Hare Intl

Mon 5/5

7:13 pm-12:32 pm

1 stop22h 19m

$479

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 5/5

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Wed 5/7

9:00 am-9:32 pm

1 stop17h 32m

$487

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 4/15

10:00 pm-6:05 pm

2 stops15h 05m

Chicago O'Hare Intl

Sat 4/19

7:50 am-6:44 pm

1 stop15h 54m

$488

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/20

9:46 pm-11:56 pm

1 stop21h 10m

Chicago O'Hare Intl

Tue 5/27

7:59 pm-11:10 am

1 stop20h 11m

$496

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/29

11:45 pm-6:05 am

1 stop25h 20m

Chicago O'Hare Intl

Tue 5/6

6:58 pm-9:40 am

1 stop19h 42m

$519

LihueChicago

LIH - ORD

LIHORD

Lihue

Tue 4/15

12:49 pm-5:08 am

1 stop11h 19m

Chicago O'Hare Intl

Sat 4/19

10:44 am-7:36 pm

1 stop13h 52m

$530

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/17

11:35 am-10:30 am

2 stops17h 55m

Chicago Midway

Thu 9/25

9:10 pm-10:20 am

1 stop18h 10m

$556

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/24

2:40 pm-9:21 am

1 stop13h 41m

Chicago O'Hare Intl

Mon 4/28

6:45 am-2:10 pm

1 stop12h 25m

$559

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/15

1:45 pm-5:14 am

1 stop10h 29m

Chicago O'Hare Intl

Tue 4/22

6:00 am-2:48 pm

1 stop13h 48m

$563

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 5/6

7:00 pm-5:00 pm

2 stops17h 00m

Chicago O'Hare Intl

Fri 5/9

6:58 pm-1:15 pm

2 stops23h 17m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Hawaii to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hawaii with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Hawaii to Chicago?

Currently, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii to Chicago in March is currently the most expensive (average of $323). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HI to CHI?

Find hourly flight availability from Hawaii to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.

When flying from Hawaii to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Hawaii to Chicago

Explore weekly flight availability from Hawaii to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 1, 2025.

The most flights from USHI to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 1, 2025.
Read through reviews of airlines operating flights from Hawaii to Chicago, such as Alaska Airlines, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,277 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,344 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Hawaii to Chicago one-way?

    The cheapest airlines for a one-way flight from Hawaii to Chicago are Alaska Airlines ($236), United Airlines ($243), and Hawaiian Airlines ($249).

  • What are the most popular routes from Hawaii to Chicago?

    When deciding which route to take from Hawaii to Chicago consider Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway or Kahului - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Hawaii to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Hawaii to Chicago on time: Avianca (87%), Air New Zealand (87%), United Airlines (77%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $2,634, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $467 for that flight.

  • Can I find deals for flights from Hawaii to Chicago that include hotel bookings?

    Yes. In addition to deals on Hawaii to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hawaii to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hawaii to Chicago.

  • Can I find deals for business class flights from Hawaii to Chicago?

    Yes. Cheapflights offers flight deals from Hawaii to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hawaii to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $245). Flying from Hawaii to Chicago in March is currently the most expensive (average of $323). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Hawaii?

Book flights to Hawaii if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hawaii to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Denver to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Diego to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Newark to St. Louis flights
Minneapolis to Midway flights
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Reagan-National to Midway flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
Hartford to O'Hare Intl flights
Seattle to Midway flights
Boston to St. Louis flights
Burbank to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
LaGuardia to St. Louis flights
Cleveland to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Baltimore to Midway flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl flights

Top 5 airlines flying from Hawaii to Chicago

Discover the top 5 airlines that operate flights from Hawaii to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$671FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$659FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$571FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$392Average$826FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$418Average$740FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.