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$263+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheap 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 December 22, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/20. 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.
Wed 12/244:04 pmHNL - ORD
1 stop16h 09mMultiple Airlines
Sun 1/119:00 amORD - HNL
1 stop31h 48mMultiple Airlines
Deal found 12/20$531
This Delta deal was found by Cheapflights users on 12/22. 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 12/238:10 amHNL - ORD
1 stop11h 49mDelta
Mon 1/127:30 amORD - HNL
1 stop14h 57mDelta
Deal found 12/22$570
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 12/242:15 pmHNL - ORD
1 stop12h 14mMultiple Airlines
Wed 1/76:06 pmORD - HNL
1 stop21h 12mMultiple Airlines
Deal found 12/21$597
This Alaska Airlines deal was found by Cheapflights users on 12/20. 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.
Sat 12/2711:28 pmHNL - ORD
1 stop11h 09mMultiple Airlines
Tue 1/276:06 pmORD - HNL
1 stop21h 05mMultiple Airlines
Deal found 12/20$633
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/246:30 pmHNL - ORD
1 stop13h 42mDelta
Sun 1/117:20 amORD - HNL
2 stops18h 08mDelta
Deal found 12/20$635
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/247:00 pmHNL - ORD
Nonstop7h 57mAmerican Airlines
Sun 1/115:05 amORD - HNL
1 stop12h 58mAmerican Airlines
Deal found 12/21$663
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Tue 12/237:00 pmHNL - ORD
Nonstop7h 57mAmerican Airlines
Mon 1/125:05 amORD - HNL
1 stop12h 58mAmerican Airlines
Deal found 12/20$666
This Alaska Airlines deal was found by Cheapflights users on 12/20. 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.
Sat 12/208:13 amHNL - ORD
1 stop11h 46mMultiple Airlines
Sat 1/103:44 pmORD - HNL
1 stop33h 37mMultiple Airlines
Deal found 12/20$668
This Southwest deal was found by Cheapflights users on 12/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:25 pmHNL - MDW
1 stop14h 10mSouthwest
Mon 12/295:10 amMDW - HNL
1 stop11h 55mSouthwest
Deal found 12/20$838
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/244:45 pmHNL - MDW
1 stop12h 20mDelta
Sun 1/119:32 amMDW - HNL
2 stops15h 56mDelta
Deal found 12/20$1,531
This Delta deal was found by Cheapflights users on 12/20. 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.
Wed 12/2411:35 pmHNL - MDW
2 stops13h 44mDelta
Wed 12/319:29 amMDW - HNL
2 stops16h 31mDelta
Deal found 12/20$2,151

Find 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 December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$366
(SmartFares)

One-way from

$263
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$741

Good round-trip deal

$677 or less

Good one-way deal

$366 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 O'ahu to Chicago (CHI)
Search Deals
One-way flight from O'ahu 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 O'ahu to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from O'ahu to Chicago (CHI).
Search Deals

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 December 22, 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 1/22

7:00 pm-7:00 am

Nonstop8h 00m

Chicago O'Hare Intl

Tue 1/27

10:00 am-3:21 pm

Nonstop9h 21m

$362

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

5:00 pm-9:43 am

1 stop12h 43m

Chicago O'Hare Intl

Thu 1/22

7:00 am-4:43 pm

1 stop13h 43m

$375

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/22

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Tue 1/27

3:44 pm-12:48 pm

1 stop25h 04m

$381

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/29

8:17 am-11:37 pm

1 stop11h 20m

Chicago O'Hare Intl

Mon 2/2

9:00 am-6:53 pm

1 stop13h 53m

$381

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

9:50 pm-1:10 pm

1 stop11h 20m

Chicago O'Hare Intl

Wed 1/21

8:00 am-10:08 pm

1 stop18h 08m

$405

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 1/18

5:00 pm-9:43 am

1 stop12h 43m

Chicago O'Hare Intl

Sun 1/25

8:45 am-4:43 pm

1 stop11h 58m

$406

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 1/19

8:30 pm-2:40 pm

1 stop14h 10m

Chicago O'Hare Intl

Mon 1/26

1:00 pm-9:08 pm

1 stop12h 08m

$406

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/23

3:35 pm-12:31 pm

1 stop15h 56m

Chicago O'Hare Intl

Tue 4/28

2:20 pm-9:20 pm

1 stop12h 00m

$423

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 2/19

5:15 pm-8:40 am

1 stop11h 25m

Chicago O'Hare Intl

Mon 2/23

6:30 am-3:15 pm

1 stop12h 45m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/22

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Thu 1/29

6:00 am-3:10 pm

1 stop13h 10m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 47 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 $253). Flying from O'ahu to Chicago in July is currently the most expensive (average of $719). 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 December 22, 2025.

It’s typically best to fly out from O'ahu to Chicago in the morning. Doing so could potentially save you 29% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from O'ahu to Chicago?

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

Travelers seeking maximum savings on their O'ahu to Chicago flight should consider departing on Tuesday 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.

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 December 22, 2025.

The most flights from zzFUW to CHI are scheduled on a Tuesday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 December 22, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from O'ahu to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Alaska Airlines
8.0
Very good
11,499 reviews
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Southwest
8.0
Very good
4,254 reviews
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Delta
7.9
Good
8,014 reviews
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
United Airlines
7.4
Good
9,102 reviews
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
American Airlines
7.2
Good
11,052 reviews
Alaska Airlines
8.0
Very good
11,499 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

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.

  • How long is the flight from O'ahu to Chicago?

    For as low as $362, American Airlines can have you in Chicago from O'ahu in 8h. There are 4234 mi between O'ahu and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from O'ahu to Chicago one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $217. However, be on the lookout for offers from Hawaiian Airlines and Alaska Airlines, 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: United Airlines (85%), Air New Zealand (85%), Avianca( 78%).

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

    While on average a flight from O'ahu to Chicago is generally $843, 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 $366 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 $253). Flying from O'ahu to Chicago in July is currently the most expensive (average of $719). 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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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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$305Average$620FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$770FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$467Average$769FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$512Average$784FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$778FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$717Average$1,047FlexibilityNo cancel feeOn-time69%

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