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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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$465
(Alaska Airlines)

One-way from

$212
(American Airlines)

Popular in

June

Cheapest in

November

Average price

$875

Good round-trip deal

$888 or less

Good one-way deal

$389 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. 8% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 9/412:16 pmKOA - ORD
1 stop11h 44mAlaska Airlines
Mon 9/81:01 pmORD - KOA
1 stop14h 08mAlaska Airlines
Deal found 7/1$465
This American Airlines deal was found by Cheapflights users on 7/3. 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 9/31:14 pmOGG - ORD
1 stop11h 47mAmerican Airlines
Sat 9/66:00 amORD - OGG
1 stop10h 44mAmerican Airlines
Deal found 7/3$465
This Delta deal was found by Cheapflights users on 7/3. 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 9/39:10 pmOGG - ORD
1 stop11h 07mDelta
Sat 9/66:10 amORD - OGG
2 stops15h 58mDelta
Deal found 7/3$471
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:30 pmKOA - MDW
1 stop14h 55mSouthwest
Mon 9/85:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 7/1$479
This Southwest deal was found by Cheapflights users on 7/3. 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 8/206:00 amITO - ORD
2 stops12h 40mSouthwest
Tue 8/266:15 amORD - ITO
2 stops20h 25mSouthwest
Deal found 7/3$522
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 8/228:30 pmOGG - MDW
1 stop15h 00mSouthwest
Sun 9/78:20 amMDW - OGG
1 stop13h 10mSouthwest
Deal found 7/2$524
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 8/2410:38 pmOGG - ORD
1 stop27h 25mAlaska Airlines
Sat 9/612:05 pmORD - OGG
1 stop14h 33mAlaska Airlines
Deal found 7/2$550
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/129:40 pmKOA - ORD
2 stops13h 10mAmerican Airlines
Sun 8/175:00 amORD - KOA
1 stop14h 04mAmerican Airlines
Deal found 7/2$569
This Delta deal was found by Cheapflights users on 7/2. 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 8/129:47 pmKOA - ORD
1 stop10h 30mDelta
Sun 8/177:15 amORD - KOA
1 stop15h 19mDelta
Deal found 7/2$574
This Southwest deal was found by Cheapflights users on 6/30. 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.
Sat 10/48:30 pmKOA - ORD
1 stop12h 55mSouthwest
Sun 10/126:15 amORD - KOA
1 stop11h 15mSouthwest
Deal found 6/30$579
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:42 pmHNL - ORD
1 stop13h 36mDelta
Thu 8/217:45 amORD - HNL
2 stops16h 20mDelta
Deal found 7/1$658
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/38:45 pmOGG - ORD
1 stop13h 35mSouthwest
Tue 8/196:15 amORD - OGG
1 stop11h 10mSouthwest
Deal found 7/1$669

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 July 3, 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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/4

12:16 pm-5:00 am

1 stop11h 44m

Chicago O'Hare Intl

Mon 9/8

1:01 pm-10:09 pm

1 stop14h 08m

$465

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 9/3

1:14 pm-6:01 am

1 stop11h 47m

Chicago O'Hare Intl

Sat 9/6

6:00 am-11:44 am

1 stop10h 44m

$465

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 9/3

9:10 pm-1:17 pm

1 stop11h 07m

Chicago O'Hare Intl

Sat 9/6

6:10 am-5:08 pm

2 stops15h 58m

$471

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/4

8:30 pm-4:25 pm

1 stop14h 55m

Chicago Midway

Mon 9/8

5:15 am-12:10 pm

1 stop11h 55m

$479

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 8/20

6:00 am-11:40 pm

2 stops12h 40m

Chicago O'Hare Intl

Tue 8/26

6:15 am-9:40 pm

2 stops20h 25m

$522

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 8/22

8:30 pm-4:30 pm

1 stop15h 00m

Chicago Midway

Sun 9/7

8:20 am-4:30 pm

1 stop13h 10m

$524

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sun 8/24

10:38 pm-7:03 am

1 stop27h 25m

Chicago O'Hare Intl

Tue 9/9

2:07 pm-8:39 pm

1 stop11h 32m

$550

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 8/12

9:40 pm-3:50 pm

2 stops13h 10m

Chicago O'Hare Intl

Sun 8/17

5:00 am-2:04 pm

1 stop14h 04m

$569

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 8/12

9:47 pm-1:17 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 8/17

7:15 am-5:34 pm

1 stop15h 19m

$574

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 10/4

8:30 pm-2:25 pm

1 stop12h 55m

Chicago O'Hare Intl

Sun 10/12

6:15 am-12:30 pm

1 stop11h 15m

$579

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 July 3, 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 July 3, 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).

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 July 3, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Hawaii to Chicago have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

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

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

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
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

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
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

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
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Crew

8.5

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), Alaska Airlines ($220), and Delta ($233).

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

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,200, our data shows the cheapest flight currently is $265. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $465 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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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$223Average$593FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$280Average$746FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$615FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$418Average$778FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$429Average$877FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$606Average$776FlexibilityNo cancel feeOn-time63%

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