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$271+ Cheap flights from O'ahu 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheap flight deals from O'ahu to Chicago

Keep the following information in mind while searching for O'ahu to Chicago flight deals. Data was last updated June 16, 2025.

Round-trip from

$562
(Alaska Airlines)

One-way from

$271
(Alaska Airlines)

Popular in

June

Cheapest in

November

Average price

$882

Good round-trip deal

$811 or less

Good one-way deal

$396 or less
From O'ahu to Chicago (CHI)
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One-way flight from O'ahu to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from O'ahu to Chicago (CHI).
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Price to beat on a one-way flight from O'ahu to Chicago (CHI).
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Find flight deals from O'ahu to Chicago

Cheapest flights from O'ahu to Chicago
Explore the most affordable flight options available from O'ahu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Thu 10/29:30 pmHNL - ORD
2 stops19h 34mAlaska Airlines
Mon 10/68:20 amORD - HNL
1 stop12h 25mAlaska Airlines
Deal found 6/16$562
This Delta deal was found by Cheapflights users on 6/14. 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 11/64:40 pmHNL - ORD
1 stop13h 24mDelta
Mon 11/247:00 amORD - HNL
1 stop12h 15mDelta
Deal found 6/14$564
This Southwest deal was found by Cheapflights users on 6/14. 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 10/28:15 amHNL - MDW
2 stops15h 45mSouthwest
Mon 10/69:00 amMDW - HNL
2 stops17h 00mSouthwest
Deal found 6/14$568
This Delta deal was found by Cheapflights users on 6/16. 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.
Thu 8/211:15 pmHNL - MDW
2 stops14h 36mDelta
Tue 8/266:00 amMDW - HNL
1 stop12h 15mDelta
Deal found 6/16$569
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Mon 8/49:15 pmHNL - ORD
2 stops16h 03mMultiple Airlines
Mon 8/187:18 pmORD - HNL
1 stop21h 47mMultiple Airlines
Deal found 6/15$603
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:50 pmHNL - ORD
1 stop11h 06mAmerican Airlines
Wed 11/1210:00 amORD - HNL
Nonstop9h 15mAmerican Airlines
Deal found 6/15$662
This Hawaiian Airlines deal was found by Cheapflights users on 6/14. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/149:25 pmHNL - ORD
1 stop10h 42mHawaiian Airlines
Thu 8/2110:00 amORD - HNL
1 stop14h 07mHawaiian Airlines
Deal found 6/14$671
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 7/151:30 pmHNL - ORD
2 stops17h 22mUnited Airlines
Tue 7/227:40 pmORD - HNL
1 stop25h 21mUnited Airlines
Deal found 6/15$770
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/179:00 pmHNL - ORD
2 stops14h 45mSouthwest
Wed 6/256:15 amORD - HNL
2 stops17h 15mSouthwest
Deal found 6/15$784

Cheapflights Fare Finder

Customize your flight search to find flights from O'ahu 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 June 16, 2025.
Use the filters below to find and compare flights from O'ahu to Chicago that are best for you.

Fly from

O'ahu

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 10/2

9:30 pm-10:04 pm

2 stops19h 34m

Chicago O'Hare Intl

Mon 10/6

8:20 am-3:45 pm

1 stop12h 25m

$562

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 11/6

4:40 pm-10:04 am

1 stop13h 24m

Chicago O'Hare Intl

Mon 11/24

7:00 am-3:15 pm

1 stop12h 15m

$564

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 10/2

8:15 am-5:00 am

2 stops15h 45m

Chicago Midway

Mon 10/6

9:00 am-9:00 pm

2 stops17h 00m

$568

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 8/21

1:15 pm-8:51 am

2 stops14h 36m

Chicago Midway

Tue 8/26

6:00 am-1:15 pm

1 stop12h 15m

$569

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 8/4

9:15 pm-6:18 pm

2 stops16h 03m

Chicago O'Hare Intl

Mon 8/18

7:18 pm-12:05 pm

1 stop21h 47m

$603

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 11/6

7:50 pm-10:56 am

1 stop11h 06m

Chicago O'Hare Intl

Wed 11/12

10:00 am-3:15 pm

Nonstop9h 15m

$662

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 8/14

9:25 pm-1:07 pm

1 stop10h 42m

Chicago O'Hare Intl

Thu 8/21

10:00 am-7:07 pm

1 stop14h 07m

$671

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 7/15

1:30 pm-11:52 am

2 stops17h 22m

Chicago O'Hare Intl

Tue 7/22

7:40 pm-4:01 pm

1 stop25h 21m

$770

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 6/26

8:10 am-11:40 pm

1 stop10h 30m

Chicago O'Hare Intl

Tue 7/1

6:15 am-6:30 pm

2 stops17h 15m

$843

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 9/11

8:43 pm-11:59 pm

2 stops22h 16m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 18 results
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Best time to book a flight from O'ahu to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from O'ahu 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 O'ahu to Chicago

What is the cheapest month to book a flight from O'ahu to Chicago?

Currently, August is the cheapest month in which you can book a flight from O'ahu to Chicago (average of $245). Flying from O'ahu 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 FUW to CHI?

Find hourly flight availability from O'ahu 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 June 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from O'ahu to Chicago as you normally would.

Weekly flight availability from O'ahu to Chicago

Explore weekly flight availability from O'ahu 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 June 16, 2025.

The most flights from zzFUW 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 June 16, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from O'ahu to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

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

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

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
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

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
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,500 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

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
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

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 O'ahu 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 O'ahu to Chicago one-way?

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $271. However, be on the lookout for offers from Delta and Southwest, as they are both options that can get you from O'ahu to Chicago for a low price.

  • What are the most popular routes from O'ahu to Chicago?

    While some choose either Honolulu - Chicago Midway or Honolulu - Chicago Greater Rockford, Honolulu - Chicago O'Hare Intl is the most popular route from O'ahu to Chicago.

  • What are the most reliable airlines from O'ahu to Chicago?

    Before booking your flight to Chicago from O'ahu, check out the most reliable airlines to get you to your destination on time: Avianca (92%), United Airlines (92%), Air New Zealand( 92%).

  • What are the cheapest flights from O'ahu to Chicago?

    While on average a flight from O'ahu to Chicago is generally $1,344, our data shows the cheapest flight currently is $294. 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 O'ahu to Chicago that include hotel bookings?

    Yes. In addition to deals on O'ahu to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'ahu to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'ahu to Chicago.

  • Can I find deals for business class flights from O'ahu to Chicago?

    Yes. Cheapflights offers flight deals from O'ahu 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 O'ahu to Chicago?

    Currently, August is the cheapest month in which you can book a flight from O'ahu to Chicago (average of $245). Flying from O'ahu 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 O'ahu?

Book flights to O'ahu if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from O'ahu to Chicago

Discover the top 6 airlines that operate flights from O'ahu 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$280Average$777FlexibilityNo cancel feeOn-time85%
DeltaCheapest$301Average$606FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$422Average$690FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$461Average$728FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$606Average$783FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$778Average$1,091FlexibilityNo cancel feeOn-time69%

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