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$196+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Hawaii to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hawaii (USHI) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$423
(American Airlines)

One-way from

$196
(American Airlines)

Good round-trip deal

$559 or less

Good one-way deal

$279 or less
From Hawaii to Chicago (CHI)
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One-way flight from Hawaii to Chicago (CHI)
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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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/21. 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.
Wed 2/59:30 pmLIH - ORD
1 stop10h 39mAmerican Airlines
Sun 2/99:45 amORD - LIH
1 stop14h 01mAmerican Airlines
Deal found 1/21$423
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/207:05 amHNL - ORD
1 stop12h 52mAmerican Airlines
Wed 3/52:13 pmORD - HNL
1 stop12h 28mAmerican Airlines
Deal found 1/20$437
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 2/510:51 pmLIH - MDW
2 stops14h 52mDelta
Sun 2/99:33 amMDW - LIH
2 stops14h 36mDelta
Deal found 1/21$444
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 2/59:34 pmLIH - ORD
2 stops13h 56mDelta
Sun 2/96:15 amORD - LIH
2 stops17h 54mDelta
Deal found 1/21$444
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/201:55 pmHNL - ORD
1 stop11h 33mMultiple Airlines
Wed 3/53:31 pmORD - HNL
2 stops26h 24mMultiple Airlines
Deal found 1/20$449
This Delta deal was found by Cheapflights users on 1/20. 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 2/1811:25 pmHNL - ORD
2 stops15h 00mDelta
Thu 2/272:10 pmORD - HNL
1 stop11h 51mDelta
Deal found 1/20$450
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/209:40 pmHNL - MDW
2 stops22h 37mMultiple Airlines
Wed 3/57:05 amMDW - HNL
2 stops19h 36mMultiple Airlines
Deal found 1/20$454
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/139:45 pmKOA - ORD
1 stop12h 01mAmerican Airlines
Sat 2/229:50 amORD - KOA
1 stop14h 22mAmerican Airlines
Deal found 1/20$465
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Mon 2/242:55 pmOGG - ORD
1 stop10h 01mAmerican Airlines
Tue 3/46:00 amORD - OGG
1 stop13h 56mAmerican Airlines
Deal found 1/19$479
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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 2/241:35 pmOGG - ORD
2 stops19h 29mAlaska Airlines
Tue 3/45:54 pmORD - OGG
1 stop23h 46mAlaska Airlines
Deal found 1/19$505
This Delta deal was found by Cheapflights users on 1/21. 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 3/2512:35 pmOGG - ORD
2 stops15h 43mDelta
Wed 4/27:30 amORD - OGG
1 stop16h 49mDelta
Deal found 1/21$506
This Delta deal was found by Cheapflights users on 1/20. 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 4/228:30 pmKOA - ORD
1 stop12h 01mDelta
Wed 4/307:30 amORD - KOA
1 stop15h 12mDelta
Deal found 1/20$509

Find flights from Hawaii to Chicago within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 2/5

9:30 pm-12:09 pm

1 stop10h 39m

Chicago O'Hare Intl

Sun 2/9

9:45 am-7:46 pm

1 stop14h 01m

$423

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 2/20

7:05 am-11:57 pm

1 stop12h 52m

Chicago O'Hare Intl

Wed 3/5

2:13 pm-10:41 pm

1 stop12h 28m

$437

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 2/18

11:25 pm-6:25 pm

2 stops15h 00m

Chicago O'Hare Intl

Wed 2/26

2:10 pm-10:01 pm

1 stop11h 51m

$439

LihueChicago

LIH - MDW

LIHMDW

Lihue

Wed 2/5

10:51 pm-5:43 pm

2 stops14h 52m

Chicago Midway

Sun 2/9

9:33 am-8:09 pm

2 stops14h 36m

$444

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 2/5

9:34 pm-3:30 pm

2 stops13h 56m

Chicago O'Hare Intl

Sun 2/9

6:15 am-8:09 pm

2 stops17h 54m

$444

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 2/20

1:55 pm-5:28 am

1 stop11h 33m

Chicago O'Hare Intl

Wed 3/5

3:31 pm-1:55 pm

2 stops26h 24m

$449

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/20

9:40 pm-12:17 am

2 stops22h 37m

Chicago Midway

Wed 3/5

7:05 am-10:41 pm

2 stops19h 36m

$454

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 2/13

9:45 pm-1:46 pm

1 stop12h 01m

Chicago O'Hare Intl

Sat 2/22

9:50 am-8:12 pm

1 stop14h 22m

$465

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/24

2:55 pm-4:56 am

1 stop10h 01m

Chicago O'Hare Intl

Tue 3/4

6:00 am-3:56 pm

1 stop13h 56m

$479

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 2/24

1:35 pm-1:04 pm

2 stops19h 29m

Chicago O'Hare Intl

Tue 3/4

5:54 pm-1:40 pm

1 stop23h 46m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Hawaii to Chicago

Get recent, data-driven insights about flights from Hawaii to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 January 21, 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 January 21, 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 January 21, 2025.
Read through reviews of airlines operating flights from Hawaii to Chicago, such as Alaska Airlines, United Airlines and Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,333 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 ($196), Southwest ($234), and Delta ($257).

  • 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 (95%), Air New Zealand (95%), United Airlines (91%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,583, our data shows the cheapest flight currently is $279. 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 $320). 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

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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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John F Kennedy Intl to Midway flights
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LaGuardia to Midway flights
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Raleigh to O'Hare Intl flights
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San Francisco to Midway flights
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Minneapolis to Midway flights
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Newark to St. Louis flights
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Boston to Midway flights
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Portland to O'Hare Intl flights

Top 4 airlines flying from Hawaii to Chicago

Discover the top 4 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$713FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$659FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$584FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$392Average$875FlexibilityNo cancel feeOn-time69%
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