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$228+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$429
(Alaska Airlines)

One-way from

$228
(American Airlines)

Popular in

June

Cheapest in

October

Average price

$736

Good round-trip deal

$554 or less

Good one-way deal

$284 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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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. 13% potential increase in price ($112 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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).
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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 February 20, 2025.

This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/711:26 pmLIH - ORD
1 stop20h 33mAlaska Airlines
Tue 3/112:00 pmORD - LIH
2 stops23h 41mAlaska Airlines
Deal found 2/20$429
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/79:30 pmLIH - ORD
1 stop11h 28mAmerican Airlines
Tue 3/117:09 amORD - LIH
1 stop14h 33mAmerican Airlines
Deal found 2/20$443
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:25 pmOGG - MDW
1 stop12h 47mDelta
Mon 3/106:00 amMDW - OGG
1 stop15h 41mDelta
Deal found 2/19$455
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 3/63:20 pmOGG - ORD
1 stop10h 33mAlaska Airlines
Mon 3/107:45 amORD - OGG
1 stop13h 07mAlaska Airlines
Deal found 2/19$455
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/55:05 pmHNL - MDW
1 stop13h 07mDelta
Mon 3/106:00 amMDW - HNL
1 stop13h 19mDelta
Deal found 2/19$455
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/58:15 amHNL - ORD
1 stop11h 41mDelta
Mon 3/106:45 amORD - HNL
1 stop12h 24mDelta
Deal found 2/19$455
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:25 pmOGG - ORD
2 stops15h 30mDelta
Mon 3/107:05 amORD - OGG
1 stop14h 36mDelta
Deal found 2/19$461
This Delta deal was found by Cheapflights users on 2/20. 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 4/229:30 pmKOA - ORD
2 stops15h 00mDelta
Wed 4/307:50 amORD - KOA
1 stop14h 49mDelta
Deal found 2/20$489
This American Airlines deal was found by Cheapflights users on 2/18. 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 4/95:50 pmOGG - ORD
1 stop10h 37mAmerican Airlines
Mon 4/216:55 amORD - OGG
1 stop12h 49mAmerican Airlines
Deal found 2/18$501
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 3/34:20 pmHNL - ORD
2 stops21h 40mAlaska Airlines
Thu 3/67:45 amORD - HNL
1 stop19h 10mAlaska Airlines
Deal found 2/18$505
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 4/299:39 pmHNL - ORD
1 stop14h 45mAmerican Airlines
Tue 5/67:25 amORD - HNL
1 stop16h 53mAmerican Airlines
Deal found 2/19$523
This Delta deal was found by Cheapflights users on 2/20. 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.
Mon 3/108:15 pmLIH - ORD
1 stop12h 09mDelta
Mon 3/177:30 amORD - LIH
1 stop16h 20mDelta
Deal found 2/20$533

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 February 20, 2025.

Fly from

Hawaii

Fly to

Chicago

Route

Depart

Return

Price

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 3/7

11:26 pm-11:59 pm

1 stop20h 33m

Chicago O'Hare Intl

Tue 3/11

2:00 pm-8:41 am

2 stops23h 41m

$429

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 3/7

9:30 pm-12:58 pm

1 stop11h 28m

Chicago O'Hare Intl

Tue 3/11

7:09 am-4:42 pm

1 stop14h 33m

$443

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 3/6

5:25 pm-10:12 am

1 stop12h 47m

Chicago Midway

Mon 3/10

6:00 am-4:41 pm

1 stop15h 41m

$455

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/6

3:20 pm-5:53 am

1 stop10h 33m

Chicago O'Hare Intl

Mon 3/10

7:45 am-3:52 pm

1 stop13h 07m

$455

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/5

5:05 pm-10:12 am

1 stop13h 07m

Chicago Midway

Mon 3/10

6:00 am-2:19 pm

1 stop13h 19m

$455

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 3/5

8:15 am-11:56 pm

1 stop11h 41m

Chicago O'Hare Intl

Mon 3/10

6:45 am-2:09 pm

1 stop12h 24m

$455

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 3/6

5:25 pm-12:55 pm

2 stops15h 30m

Chicago O'Hare Intl

Mon 3/10

7:05 am-4:41 pm

1 stop14h 36m

$461

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/22

9:30 pm-5:30 pm

2 stops15h 00m

Chicago O'Hare Intl

Wed 4/30

7:50 am-5:39 pm

1 stop14h 49m

$489

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 4/9

5:50 pm-9:27 am

1 stop10h 37m

Chicago O'Hare Intl

Mon 4/21

6:55 am-2:44 pm

1 stop12h 49m

$501

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/3

4:20 pm-6:00 pm

2 stops21h 40m

Chicago O'Hare Intl

Thu 3/6

7:45 am-10:55 pm

1 stop19h 10m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 58 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 $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 February 20, 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 February 20, 2025.

The most flights from USHI to CHI are scheduled on a Thursday (4 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (2 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 February 20, 2025.
Read through reviews of airlines operating flights from Hawaii to Chicago, such as Southwest, Alaska Airlines and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($228), Delta ($233), and Alaska Airlines ($255).

  • 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: Air New Zealand (88%), Avianca (88%), United Airlines (80%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,498, 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 $455 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
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.
John F Kennedy Intl to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
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Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Newark to St. Louis flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Dulles Intl to St. Louis flights
Denver to Midway 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$709FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$653FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$567FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$392Average$876FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$418Average$617FlexibilityNo cancel feeOn-time63%
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