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$186+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$444
(Kiwi.com)

One-way from

$186
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$712

Good round-trip deal

$657 or less

Good one-way deal

$304 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 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. 12% potential increase in price ($104 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 November 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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Tue 12/28:00 amHNL - ORD
1 stop18h 25mMultiple Airlines
Tue 12/99:06 pmORD - HNL
2 stops21h 55mMultiple Airlines
Deal found 11/4$444
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/54:06 pmHNL - ORD
1 stop28h 07mMultiple Airlines
Wed 12/109:06 pmORD - HNL
2 stops22h 34mMultiple Airlines
Deal found 11/4$455
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/154:06 pmHNL - ORD
1 stop33h 59mMultiple Airlines
Mon 12/297:44 pmORD - HNL
1 stop19h 28mMultiple Airlines
Deal found 11/1$456
This Delta deal was found by Cheapflights users on 11/4. 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 12/154:45 pmHNL - ORD
1 stop13h 15mDelta
Thu 1/16:45 amORD - HNL
1 stop14h 15mDelta
Deal found 11/4$461
This Alaska Airlines deal was found by Cheapflights users on 11/4. 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 12/2311:28 pmHNL - ORD
1 stop16h 34mAlaska Airlines
Mon 1/123:49 pmORD - HNL
1 stop24h 59mAlaska Airlines
Deal found 11/4$462
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/158:00 amHNL - ORD
1 stop12h 13mMultiple Airlines
Thu 1/17:44 pmORD - HNL
1 stop19h 28mMultiple Airlines
Deal found 11/4$474
This Delta deal was found by Cheapflights users on 11/4. 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 12/1511:23 pmHNL - MDW
2 stops14h 55mDelta
Thu 1/16:00 amMDW - HNL
1 stop15h 00mDelta
Deal found 11/4$588
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/159:25 pmHNL - MDW
1 stop10h 10mSouthwest
Thu 1/18:20 amMDW - HNL
1 stop16h 40mSouthwest
Deal found 11/4$601
This Southwest deal was found by Cheapflights users on 11/3. 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.
Mon 11/248:00 amHNL - MDW
2 stops12h 25mSouthwest
Mon 12/15:10 amMDW - HNL
1 stop11h 55mSouthwest
Deal found 11/3$606
This Southwest deal was found by Cheapflights users on 11/3. 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 11/269:25 pmHNL - MDW
1 stop10h 15mSouthwest
Sat 11/298:10 amMDW - HNL
2 stops16h 50mSouthwest
Deal found 11/3$698
This Delta deal was found by Cheapflights users on 11/2. 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 12/152:45 pmHNL - MDW
2 stops14h 34mDelta
Mon 12/296:00 amMDW - HNL
1 stop13h 04mDelta
Deal found 11/2$701
This Southwest deal was found by Cheapflights users on 11/1. 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 11/129:25 pmHNL - MDW
1 stop11h 40mSouthwest
Wed 11/265:10 amMDW - HNL
1 stop11h 55mSouthwest
Deal found 11/1$705

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 November 4, 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

Tue 12/23

11:28 pm-8:02 pm

1 stop16h 34m

Chicago O'Hare Intl

Mon 1/12

3:49 pm-12:48 pm

1 stop24h 59m

$462

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 1/18

5:15 pm-1:18 pm

2 stops16h 03m

Chicago O'Hare Intl

Sun 2/1

7:30 am-5:07 pm

1 stop13h 37m

$496

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 12/5

7:45 pm-2:09 pm

2 stops14h 24m

Chicago O'Hare Intl

Wed 12/10

8:55 am-5:50 pm

2 stops12h 55m

$510

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 12/3

9:36 pm-12:13 am

1 stop22h 37m

Chicago O'Hare Intl

Wed 12/17

9:06 pm-11:12 am

1 stop18h 06m

$519

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/7

9:40 pm-2:29 pm

2 stops12h 49m

Chicago O'Hare Intl

Wed 1/14

9:00 am-9:21 pm

1 stop16h 21m

$526

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/7

12:58 pm-11:37 pm

1 stop30h 39m

Chicago O'Hare Intl

Mon 1/12

3:49 pm-12:48 pm

1 stop24h 59m

$532

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 1/18

4:44 pm-8:54 am

1 stop12h 10m

Chicago Midway

Sun 2/1

6:00 am-3:11 pm

1 stop13h 11m

$547

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 12/22

11:48 pm-12:12 am

2 stops44h 24m

Chicago O'Hare Intl

Mon 12/29

7:44 pm-11:12 am

1 stop19h 28m

$548

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 12/23

8:10 am-11:59 pm

1 stop11h 49m

Chicago O'Hare Intl

Mon 1/12

7:20 am-9:28 pm

2 stops18h 08m

$551

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 12/15

11:23 pm-6:18 pm

2 stops14h 55m

Chicago Midway

Thu 1/1

6:00 am-5:00 pm

1 stop15h 00m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 42 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 $658). 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 November 4, 2025.

It’s typically best to fly out from O'ahu to Chicago in the morning. Doing so could potentially save you 30% 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 November 4, 2025.

The most flights from zzFUW to CHI are scheduled on a Monday (6 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 November 4, 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
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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
11,241 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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
4,239 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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
7.9
Good
8,003 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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
9,002 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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
11,040 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.0

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 $601, Alaska Airlines can have you in Chicago from O'ahu in 10h 10m. There are 4243 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 Alaska Airlines, with whom users have recently found tickets for as low as $230. 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 (93%), 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 $1,699, 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 $485 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 $658). 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
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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$669FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$770FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$442Average$750FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$467Average$767FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$516Average$773FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$735Average$1,063FlexibilityNo cancel feeOn-time69%

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