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$239+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$555
(Delta)

One-way from

$239
(Delta)

Popular in

July

Cheapest in

October

Average price

$644

Good round-trip deal

$770 or less

Good one-way deal

$411 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. 7% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 8/2112:35 pmHNL - MDW
2 stops15h 01mDelta
Tue 8/269:30 amMDW - HNL
2 stops14h 42mDelta
Deal found 4/29$554
This American Airlines deal was found by Cheapflights users on 4/28. 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 10/3012:43 pmHNL - ORD
1 stop12h 27mAmerican Airlines
Mon 11/310:00 amORD - HNL
Nonstop9h 15mAmerican Airlines
Deal found 4/28$554
This Delta deal was found by Cheapflights users on 4/29. 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 8/143:45 pmHNL - ORD
1 stop10h 37mDelta
Tue 8/197:15 amORD - HNL
1 stop12h 19mDelta
Deal found 4/29$555
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 10/229:15 pmHNL - ORD
2 stops17h 44mAlaska Airlines
Sat 10/2510:00 amORD - HNL
2 stops17h 25mAlaska Airlines
Deal found 4/29$557
This Southwest deal was found by Cheapflights users on 4/30. 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 9/48:10 amHNL - MDW
1 stop10h 15mSouthwest
Thu 9/119:10 pmMDW - HNL
1 stop18h 10mSouthwest
Deal found 4/30$563
This Hawaiian Airlines deal was found by Cheapflights users on 4/28. 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 10/3012:40 pmHNL - ORD
1 stop11h 24mHawaiian Airlines
Mon 11/37:00 amORD - HNL
1 stop11h 50mHawaiian Airlines
Deal found 4/28$563
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 7/310:30 pmHNL - ORD
1 stop26h 09mUnited Airlines
Mon 7/149:40 pmORD - HNL
1 stop23h 49mUnited Airlines
Deal found 4/29$655
This Southwest deal was found by Cheapflights users on 4/30. 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 5/2111:15 amHNL - ORD
2 stops19h 35mSouthwest
Sat 5/245:25 pmORD - HNL
2 stops21h 55mSouthwest
Deal found 4/30$719

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 May 1, 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 8/14

3:45 pm-7:22 am

1 stop10h 37m

Chicago O'Hare Intl

Tue 8/19

7:15 am-2:34 pm

1 stop12h 19m

$555

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 10/22

9:15 pm-7:59 pm

2 stops17h 44m

Chicago O'Hare Intl

Sat 10/25

10:00 am-10:25 pm

2 stops17h 25m

$557

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 5/23

1:20 pm-8:36 am

2 stops14h 16m

Chicago Midway

Fri 5/30

9:16 am-8:44 pm

2 stops16h 28m

$558

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 6/5

8:27 pm-2:15 pm

1 stop12h 48m

Chicago O'Hare Intl

Tue 6/10

3:12 pm-9:55 pm

1 stop11h 43m

$587

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 9/9

9:05 pm-2:10 pm

2 stops12h 05m

Chicago O'Hare Intl

Mon 9/15

6:55 pm-10:20 am

2 stops20h 25m

$593

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 10/19

1:25 pm-5:04 am

1 stop10h 39m

Chicago O'Hare Intl

Thu 10/23

10:00 am-5:17 pm

1 stop12h 17m

$603

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 7/3

10:30 pm-5:39 am

1 stop26h 09m

Chicago O'Hare Intl

Mon 7/14

9:40 pm-4:29 pm

1 stop23h 49m

$655

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 7/16

11:00 am-5:00 am

1 stop13h 00m

Chicago Midway

Wed 7/30

2:50 pm-9:15 pm

1 stop11h 25m

$713

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 9/5

12:35 pm-8:31 am

2 stops14h 56m

$239

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sat 5/31

6:20 am-11:59 pm

1 stop12h 39m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 16 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 May 1, 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 May 1, 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 May 1, 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
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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
2,409 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.1

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 Delta, with whom users have recently found tickets for as low as $239. However, be on the lookout for offers from American 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: Air New Zealand (88%), Avianca (88%), United Airlines( 82%).

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

    While on average a flight from O'ahu to Chicago is generally $2,240, our data shows the cheapest flight currently is $299. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $442 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$280Average$777FlexibilityNo cancel feeOn-time85%
DeltaCheapest$291Average$773FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$418Average$753FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$421Average$661FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$444Average$713FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$783Average$1,086FlexibilityNo cancel feeOn-time69%

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