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$212+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
יוני 18 — יוני 251
ד' 6/18
ד' 6/25
1 adult, Economy
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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 יוני 13, 2025.

Round-trip from

$437
(American Airlines)

One-way from

$212
(American Airlines)

Popular in

July

Cheapest in

November

Average price

$882

Good round-trip deal

$766 or less

Good one-way deal

$395 or less
From Hawaii to Chicago (CHI)
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One-way flight from Hawaii to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Hawaii to Chicago (CHI).
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Price to beat on a one-way flight from Hawaii to Chicago (CHI).
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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 יוני 13, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
ג' 8/129:46 pmOGG - ORD
1 stop10h 58mAmerican Airlines
ד' 8/2011:45 amORD - OGG
1 stop13h 39mAmerican Airlines
Deal found 6/11$437
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
ג' 8/1210:34 pmOGG - ORD
2 stops14h 44mAlaska Airlines
ד' 8/2010:00 amORD - OGG
2 stops17h 11mAlaska Airlines
Deal found 6/11$514
This United Airlines deal was found by Cheapflights users on 6/11. 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.
ג' 6/177:40 pmLIH - ORD
1 stop12h 41mUnited Airlines
ג' 7/11:55 pmORD - LIH
1 stop11h 30mUnited Airlines
Deal found 6/11$529
This Delta deal was found by Cheapflights users on 6/11. 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.
ב' 10/612:35 pmHNL - ORD
2 stops15h 04mDelta
ג' 10/147:30 amORD - HNL
2 stops17h 20mDelta
Deal found 6/11$559
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
ו' 10/1010:20 pmHNL - ORD
1 stop11h 30mAlaska Airlines
ג' 10/148:20 amORD - HNL
2 stops19h 02mAlaska Airlines
Deal found 6/11$560
This Delta deal was found by Cheapflights users on 6/10. 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.
ג' 8/121:15 pmHNL - MDW
2 stops14h 35mDelta
ה' 8/149:15 amMDW - HNL
2 stops16h 13mDelta
Deal found 6/10$561
This Southwest deal was found by Cheapflights users on 6/12. 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.
ו' 11/712:35 pmHNL - MDW
2 stops12h 30mSouthwest
ד' 11/128:20 pmMDW - HNL
2 stops20h 50mSouthwest
Deal found 6/12$572
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ו' 8/229:30 pmHNL - ORD
1 stop10h 39mHawaiian Airlines
ג' 8/2610:00 amORD - HNL
1 stop14h 07mHawaiian Airlines
Deal found 6/11$576
This American Airlines deal was found by Cheapflights users on 6/12. 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.
ה' 11/67:00 pmHNL - ORD
Nonstop8h 10mAmerican Airlines
ב' 11/249:50 amORD - HNL
1 stop13h 47mAmerican Airlines
Deal found 6/12$577
This Southwest deal was found by Cheapflights users on 6/12. 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.
ה' 10/29:10 pmHNL - ORD
2 stops14h 35mSouthwest
ב' 10/66:55 pmORD - HNL
2 stops20h 25mSouthwest
Deal found 6/12$587
This Alaska Airlines deal was found by Cheapflights users on 6/11. 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.
ד' 7/308:00 amKOA - ORD
1 stop10h 59mAlaska Airlines
ד' 8/67:18 pmORD - KOA
1 stop19h 12mAlaska Airlines
Deal found 6/11$621
This Delta deal was found by Cheapflights users on 6/13. 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.
ד' 7/309:47 pmKOA - ORD
1 stop14h 33mDelta
ד' 8/66:00 amORD - KOA
2 stops18h 00mDelta
Deal found 6/13$646

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 יוני 13, 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

KahuluiChicago

OGG - ORD

OGGORD

Kahului

ג' 8/12

9:46 pm-1:44 pm

1 stop10h 58m

Chicago O'Hare Intl

ד' 8/20

11:45 am-8:24 pm

1 stop13h 39m

$437

KahuluiChicago

OGG - ORD

OGGORD

Kahului

ג' 8/12

10:34 pm-6:18 pm

2 stops14h 44m

Chicago O'Hare Intl

ד' 8/20

10:00 am-10:11 pm

2 stops17h 11m

$514

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ב' 10/6

12:35 pm-8:39 am

2 stops15h 04m

Chicago O'Hare Intl

ג' 10/14

7:30 am-7:50 pm

2 stops17h 20m

$559

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ו' 10/10

10:20 pm-2:50 pm

1 stop11h 30m

Chicago O'Hare Intl

ג' 10/14

8:20 am-10:22 pm

2 stops19h 02m

$560

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

ג' 8/12

1:15 pm-8:50 am

2 stops14h 35m

Chicago Midway

ה' 8/14

9:15 am-8:28 pm

2 stops16h 13m

$561

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

ו' 11/7

12:35 pm-5:05 am

2 stops12h 30m

Chicago Midway

ד' 11/12

8:20 pm-1:10 pm

2 stops20h 50m

$572

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ו' 8/22

9:30 pm-1:09 pm

1 stop10h 39m

Chicago O'Hare Intl

ג' 8/26

10:00 am-7:07 pm

1 stop14h 07m

$576

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ה' 11/6

7:00 pm-7:10 am

Nonstop8h 10m

Chicago O'Hare Intl

ב' 11/24

9:50 am-7:37 pm

1 stop13h 47m

$577

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ה' 10/2

9:10 pm-4:45 pm

2 stops14h 35m

Chicago O'Hare Intl

ב' 10/6

6:55 pm-10:20 am

2 stops20h 25m

$587

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

ד' 7/30

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

ד' 8/6

7:18 pm-9:30 am

1 stop19h 12m

$621

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 60 results
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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 $321). 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 יוני 13, 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 יוני 13, 2025.

The most flights from USHI to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 יוני 13, 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
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,496 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 American Airlines ($212), Delta ($219), and Alaska Airlines ($231).

  • 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 Kona Intl - 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 (92%), Air New Zealand (92%), United Airlines (86%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,344, our data shows the cheapest flight currently is $294. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $437 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 $321). 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Hawaii to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Hobby to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to Midway flights
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LaGuardia to Midway flights
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Raleigh to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Austin to O'Hare Intl flights
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George Bush Intcntl to O'Hare Intl flights
Atlanta to Midway flights
Portland to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Oakland to O'Hare Intl flights
Miami to O'Hare Intl flights
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Los Angeles to Midway flights
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Baltimore to Midway flights
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Newark to St. Louis flights
Salt Lake City to O'Hare Intl flights
Dulles Intl to St. Louis flights

Top 6 airlines flying from Hawaii to Chicago

Discover the top 6 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 יוני 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$592FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$280Average$746FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$622FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$418Average$771FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$429Average$870FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$606Average$776FlexibilityNo cancel feeOn-time63%

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