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$190+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 7 — Dec 141
Sat 12/7
Sat 12/14
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 December 2, 2024.

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 December 2, 2024.

This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/237:05 amHNL - ORD
1 stop12h 05mAmerican Airlines
Tue 12/316:00 amORD - HNL
1 stop16h 40mAmerican Airlines
Deal found 12/1$575
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Fri 12/610:00 amKOA - ORD
1 stop28h 18mAlaska Airlines
Sat 1/116:55 pmORD - KOA
1 stop32h 49mAlaska Airlines
Deal found 12/1$576
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/69:40 pmKOA - ORD
2 stops13h 56mAmerican Airlines
Sat 1/116:30 amORD - KOA
2 stops17h 20mAmerican Airlines
Deal found 12/1$609
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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 12/54:44 pmHNL - ORD
1 stop20h 15mAlaska Airlines
Sun 12/85:59 pmORD - HNL
1 stop24h 00mAlaska Airlines
Deal found 12/1$614
This Southwest deal was found by Cheapflights users on 12/1. 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.
Wed 12/48:40 amHNL - ORD
1 stop10h 25mSouthwest
Mon 12/96:15 amORD - HNL
2 stops16h 25mSouthwest
Deal found 12/1$669
This Southwest deal was found by Cheapflights users on 12/1. 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.
Fri 12/68:40 amHNL - MDW
1 stop10h 45mSouthwest
Sun 12/85:30 amMDW - HNL
1 stop11h 55mSouthwest
Deal found 12/1$703
This Delta deal was found by Cheapflights users on 12/1. 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.
Tue 12/109:35 pmHNL - ORD
2 stops13h 03mDelta
Wed 1/86:45 amORD - HNL
1 stop12h 28mDelta
Deal found 12/1$706
This United Airlines deal was found by Cheapflights users on 12/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3110:49 pmOGG - ORD
2 stops18h 41mUnited Airlines
Tue 1/710:35 amORD - OGG
2 stops14h 19mUnited Airlines
Deal found 12/1$736
This United Airlines deal was found by Cheapflights users on 12/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/242:25 pmHNL - ORD
1 stop17h 02mUnited Airlines
Mon 12/308:20 pmORD - HNL
1 stop25h 12mUnited Airlines
Deal found 12/1$748
This Delta deal was found by Cheapflights users on 12/1. 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 12/54:55 pmHNL - MDW
1 stop12h 03mDelta
Mon 12/96:00 amMDW - HNL
1 stop13h 16mDelta
Deal found 12/1$760
This Mytrip deal was found by Cheapflights users on 12/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/239:25 pmHNL - ORD
3 stops28h 05mMultiple Airlines
Tue 12/317:00 amORD - HNL
3 stops32h 05mMultiple Airlines
Deal found 12/1$766
This Alaska Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/314:10 pmOGG - ORD
1 stop21h 49mAlaska Airlines
Tue 1/77:45 amORD - OGG
1 stop19h 12mAlaska Airlines
Deal found 12/1$798

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 2,650,959 searches. Data last updated December 2, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/22

10:40 pm-1:49 pm

1 stop11h 09m

Chicago O'Hare Intl

Wed 1/29

5:00 am-2:00 pm

1 stop13h 00m

$422

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/22

4:50 pm-8:54 am

1 stop12h 04m

Chicago Midway

Wed 1/29

10:19 am-9:56 pm

2 stops15h 37m

$427

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/22

6:40 pm-12:55 pm

2 stops14h 15m

Chicago O'Hare Intl

Wed 1/29

7:15 am-4:57 pm

1 stop13h 42m

$427

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 2/2

4:24 pm-4:27 pm

2 stops20h 03m

Chicago O'Hare Intl

Thu 2/6

3:35 pm-11:05 am

1 stop23h 30m

$448

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 1/13

2:00 pm-11:59 pm

1 stop29h 59m

Chicago O'Hare Intl

Wed 1/22

7:45 am-1:00 pm

1 stop33h 15m

$532

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/9

4:30 pm-1:07 pm

1 stop16h 37m

Chicago O'Hare Intl

Thu 1/16

7:45 am-10:57 pm

1 stop19h 12m

$540

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/2

2:45 pm-4:45 pm

2 stops22h 00m

Chicago O'Hare Intl

Fri 3/7

6:00 am-6:35 pm

2 stops16h 35m

$608

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 2/14

10:30 am-9:15 am

2 stops18h 45m

Chicago Midway

Sat 2/22

8:10 am-5:30 pm

1 stop13h 20m

$633

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/9

4:55 pm-8:35 am

1 stop11h 40m

Chicago O'Hare Intl

Thu 1/16

7:15 am-7:55 pm

1 stop16h 40m

$646

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 4/3

8:55 am-11:50 am

2 stops21h 55m

Chicago O'Hare Intl

Mon 4/7

6:00 am-4:40 pm

1 stop15h 40m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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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, September is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $232). Flying from Hawaii to Chicago in June is currently the most expensive (average of $308). 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 2, 2024.

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 December 2, 2024.

The most flights from USHI to CHI are scheduled on a Sunday (4 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 December 2, 2024.
Read through reviews of airlines operating flights from Hawaii to Chicago, such as Alaska Airlines, Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Southwest
8.1
Very good
4,951 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Alaska Airlines
8.0
Very good
9,513 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Delta
8.0
Very good
8,698 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Hawaiian Airlines
7.9
Good
2,285 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

United Airlines
7.4
Good
9,141 reviews
Southwest
8.1
Very good
4,951 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

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 ($190), Alaska Airlines ($216), and Delta ($216).

  • 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 (100%), United Airlines (100%), Air New Zealand (100%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,367, our data shows the cheapest flight currently is $262. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $422 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, September is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $232). Flying from Hawaii to Chicago in June is currently the most expensive (average of $308). 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

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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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LaGuardia to St. Louis 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 2,650,959 searches. Data last updated December 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$220Average$707FlexibilityNo cancel feeOn-time75%
DeltaCheapest$222Average$645FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$646FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$411Average$866FlexibilityNo cancel feeOn-time69%
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