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$164+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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 12/308:30 pmLIH - ORD
1 stop10h 55mUnited Airlines
Fri 1/26:15 amORD - LIH
1 stop12h 33mUnited Airlines
Deal found 12/16$453
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/318:30 pmLIH - ORD
1 stop10h 55mUnited Airlines
Fri 1/26:15 amORD - LIH
1 stop12h 33mUnited Airlines
Deal found 12/16$486
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:48 pmHNL - ORD
1 stop26h 17mMultiple Airlines
Sun 1/410:49 pmORD - HNL
2 stops53h 59mMultiple Airlines
Deal found 12/15$487
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:18 pmHNL - ORD
1 stop11h 47mMultiple Airlines
Sun 1/410:49 pmORD - HNL
2 stops53h 59mMultiple Airlines
Deal found 12/15$506
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/312:29 pmLIH - ORD
1 stop10h 58mUnited Airlines
Sun 1/48:45 amORD - LIH
1 stop12h 19mUnited Airlines
Deal found 12/15$514
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/249:56 pmHNL - ORD
1 stop11h 20mMultiple Airlines
Sun 1/119:00 amORD - HNL
1 stop31h 48mMultiple Airlines
Deal found 12/16$530
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/237:00 pmHNL - ORD
Nonstop7h 57mAmerican Airlines
Mon 1/1210:00 amORD - HNL
Nonstop9h 21mAmerican Airlines
Deal found 12/16$551
This Alaska Airlines deal was found by Cheapflights users on 12/17. 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 12/2311:28 pmHNL - ORD
1 stop16h 34mMultiple Airlines
Mon 1/123:44 pmORD - HNL
1 stop25h 04mMultiple Airlines
Deal found 12/17$556
This Delta deal was found by Cheapflights users on 12/16. 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 12/235:39 pmHNL - ORD
1 stop14h 13mDelta
Mon 1/126:50 amORD - HNL
2 stops18h 38mDelta
Deal found 12/16$576
This Southwest deal was found by Cheapflights users on 12/17. 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.
Mon 12/228:00 amHNL - MDW
1 stop12h 55mSouthwest
Sun 1/118:35 pmMDW - HNL
1 stop18h 40mSouthwest
Deal found 12/17$630
This Delta deal was found by Cheapflights users on 12/16. 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 12/244:45 pmHNL - ORD
2 stops15h 05mDelta
Sun 1/117:20 amORD - HNL
2 stops18h 08mDelta
Deal found 12/16$641
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/316:30 pmKOA - ORD
1 stop11h 14mAmerican Airlines
Sun 1/48:15 amORD - KOA
1 stop12h 23mAmerican Airlines
Deal found 12/16$712

Find flight deals from Hawaii to Chicago

Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$343
(Alaska Airlines)

One-way from

$164
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$741

Good round-trip deal

$554 or less

Good one-way deal

$292 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. 11% potential increase in price ($95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 18, 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

Tue 1/13

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$343

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$361

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/13

4:05 pm-2:29 pm

2 stops18h 24m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$369

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

9:00 pm-2:29 pm

2 stops13h 29m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$388

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 2/6

1:39 pm-2:29 pm

2 stops20h 50m

Chicago O'Hare Intl

Mon 2/9

3:44 pm-1:03 pm

1 stop25h 19m

$389

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 1/21

10:20 pm-2:38 pm

1 stop12h 18m

Chicago O'Hare Intl

Sun 1/25

9:00 am-1:45 pm

1 stop32h 45m

$392

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 2/6

10:25 am-2:29 pm

1 stop24h 04m

Chicago O'Hare Intl

Mon 2/9

3:44 pm-1:03 pm

1 stop25h 19m

$392

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/15

2:51 pm-11:37 pm

1 stop28h 46m

Chicago O'Hare Intl

Thu 1/22

3:44 pm-3:57 pm

1 stop28h 13m

$393

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 2/18

11:54 pm-11:59 pm

1 stop20h 05m

Chicago O'Hare Intl

Sun 2/22

8:20 am-11:46 pm

1 stop19h 26m

$393

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 1/21

9:00 pm-2:38 pm

2 stops13h 38m

Chicago O'Hare Intl

Sun 1/25

3:44 pm-1:45 pm

1 stop26h 01m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $689). 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 December 18, 2025.

One of the essential ways to save on airfare from Hawaii to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 39% on airfare.

What is the cheapest day to fly from Hawaii to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Hawaii to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Hawaii to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Hawaii to Chicago?

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.

  • How long is the flight from Hawaii to Chicago?

    Alaska Airlines, Delta, and Southwest can get you from Hawaii to Chicago in just under 12h 35m. Your travel time can differ by up to 7h 03m. Airlines will cover a distance of 4243 mi. This flight may include one or multiple stops.

  • 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 Southwest ($210), American Airlines ($211), and Delta ($211).

  • 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: United Airlines (85%), Air New Zealand (85%), Avianca (78%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,553, our data shows the cheapest flight currently is $258. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $410 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, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $689). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$305Average$620FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$743FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$424Average$867FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$455Average$719FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$468Average$797FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$775FlexibilityNo cancel feeOn-time63%

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