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$265+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$470
(Alaska Airlines)

One-way from

$265
(Alaska Airlines)

Popular in

July

Cheapest in

November

Average price

$618

Good round-trip deal

$577 or less

Good one-way deal

$327 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. 13% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/16. 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 10/231:20 pmHNL - ORD
2 stops14h 10mDelta
Mon 10/277:37 amORD - HNL
1 stop16h 32mDelta
Deal found 9/16$471
This Delta deal was found by Cheapflights users on 9/16. 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 12/234:45 pmHNL - ORD
1 stop12h 16mDelta
Wed 1/77:30 amORD - HNL
1 stop17h 03mDelta
Deal found 9/16$472
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Mon 1/126:00 amMDW - HNL
1 stop13h 12mDelta
Deal found 9/15$475
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:45 pmHNL - ORD
1 stop12h 16mDelta
Mon 1/127:00 amORD - HNL
1 stop12h 29mDelta
Deal found 9/17$475
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/232:50 pmHNL - ORD
1 stop12h 00mDelta
Sun 10/267:37 amORD - HNL
1 stop16h 32mDelta
Deal found 9/17$479
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/171:05 pmHNL - ORD
1 stop12h 19mAlaska Airlines
Sat 10/253:50 pmORD - HNL
1 stop25h 32mAlaska Airlines
Deal found 9/17$481
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:50 pmHNL - MDW
1 stop10h 50mDelta
Wed 11/59:20 amMDW - HNL
2 stops16h 06mDelta
Deal found 9/17$484
This Delta deal was found by Cheapflights users on 9/16. 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 10/301:20 pmHNL - ORD
2 stops14h 43mDelta
Tue 11/47:10 amORD - HNL
2 stops18h 16mDelta
Deal found 9/16$490
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Mon 1/56:00 amMDW - HNL
1 stop13h 12mDelta
Deal found 9/15$511
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/149:10 pmHNL - MDW
1 stop10h 20mSouthwest
Tue 10/2111:55 amMDW - HNL
1 stop14h 05mSouthwest
Deal found 9/16$525
This Delta deal was found by Cheapflights users on 9/16. 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 10/232:50 pmHNL - MDW
1 stop12h 50mDelta
Sun 10/269:35 amMDW - HNL
2 stops14h 34mDelta
Deal found 9/16$546
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/319:10 pmHNL - MDW
1 stop14h 40mSouthwest
Wed 11/58:55 pmMDW - HNL
1 stop18h 25mSouthwest
Deal found 9/17$556

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 September 17, 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

Sun 3/1

8:15 am-11:44 pm

1 stop11h 29m

Chicago O'Hare Intl

Tue 3/3

5:50 am-3:19 pm

1 stop13h 29m

$471

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Wed 1/7

7:30 am-8:33 pm

1 stop17h 03m

$472

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

4:45 pm-9:01 am

1 stop12h 16m

Chicago O'Hare Intl

Mon 1/12

7:00 am-3:29 pm

1 stop12h 29m

$475

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 10/14

10:31 pm-5:10 pm

1 stop13h 39m

Chicago O'Hare Intl

Tue 10/21

6:45 am-7:09 pm

2 stops17h 24m

$478

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 10/27

10:31 pm-5:10 pm

1 stop13h 39m

Chicago O'Hare Intl

Mon 11/3

7:10 am-2:51 pm

1 stop11h 41m

$479

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 11/17

4:45 pm-1:07 pm

2 stops16h 22m

Chicago Midway

Mon 1/12

6:00 am-3:12 pm

1 stop13h 12m

$480

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

4:50 pm-8:40 am

1 stop10h 50m

Chicago Midway

Wed 11/5

9:20 am-9:26 pm

2 stops16h 06m

$484

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 10/23

1:20 pm-7:50 am

2 stops13h 30m

Chicago O'Hare Intl

Sun 10/26

7:37 am-7:09 pm

1 stop16h 32m

$484

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 11/17

4:45 pm-12:04 pm

2 stops15h 19m

Chicago O'Hare Intl

Mon 1/5

7:00 am-3:29 pm

1 stop12h 29m

$484

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 11/17

4:45 pm-8:52 am

1 stop12h 07m

Chicago Midway

Mon 1/5

6:00 am-3:12 pm

1 stop13h 12m

$511

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 44 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 September 17, 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 September 17, 2025.

The most flights from zzFUW to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 September 17, 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
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
8.0
Very good
7,961 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,926 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Entertainment

7.1

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 $471, Delta can have you in Chicago from O'ahu in 11h 29m. There are 4234 mi between O'ahu and Chicago.

  • 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 $265. However, be on the lookout for offers from Southwest and Delta, 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 (97%), United Airlines (97%), Air New Zealand( 97%).

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

    While on average a flight from O'ahu to Chicago is generally $1,700, our data shows the cheapest flight currently is $254. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $467 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 Chicago?

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

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$626FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$770FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$461Average$759FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$461Average$754FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$617Average$798FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$781Average$1,084FlexibilityNo cancel feeOn-time69%

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