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$280+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$515
(Alaska Airlines)

One-way from

$280
(Alaska Airlines)

Popular in

July

Cheapest in

October

Average price

$699

Good round-trip deal

$730 or less

Good one-way deal

$369 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. 10% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:27 pmHNL - ORD
1 stop11h 52mAlaska Airlines
Fri 10/38:59 pmORD - HNL
1 stop30h 26mAlaska Airlines
Deal found 4/2$515
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/243:15 pmHNL - ORD
1 stop12h 26mDelta
Wed 4/306:45 amORD - HNL
1 stop12h 25mDelta
Deal found 4/3$531
This Southwest deal was found by Cheapflights users on 4/4. 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.
Fri 9/58:05 amHNL - MDW
1 stop11h 25mSouthwest
Mon 9/89:10 pmMDW - HNL
1 stop18h 10mSouthwest
Deal found 4/4$558
This Delta deal was found by Cheapflights users on 4/4. 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.
Sun 5/42:40 pmHNL - MDW
1 stop13h 00mDelta
Thu 5/89:16 amMDW - HNL
2 stops16h 18mDelta
Deal found 4/4$566
This American Airlines deal was found by Cheapflights users on 4/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:20 amHNL - ORD
1 stop12h 39mAmerican Airlines
Wed 5/283:15 pmORD - HNL
1 stop10h 56mAmerican Airlines
Deal found 4/3$584
This Southwest deal was found by Cheapflights users on 4/4. 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.
Fri 9/59:10 pmHNL - ORD
2 stops15h 45mSouthwest
Mon 9/86:55 pmORD - HNL
2 stops20h 25mSouthwest
Deal found 4/4$590
This United Airlines deal was found by Cheapflights users on 4/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:00 amHNL - ORD
1 stop17h 10mUnited Airlines
Fri 1/96:00 pmORD - HNL
1 stop27h 12mUnited Airlines
Deal found 4/3$674
This Hawaiian Airlines deal was found by Cheapflights users on 4/4. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/169:15 pmHNL - ORD
1 stop11h 58mHawaiian Airlines
Mon 8/187:00 amORD - HNL
1 stop11h 45mHawaiian Airlines
Deal found 4/4$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 April 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

Fri 9/26

9:27 pm-2:19 pm

1 stop11h 52m

Chicago O'Hare Intl

Fri 10/3

8:59 pm-10:25 pm

1 stop30h 26m

$515

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/24

3:15 pm-8:41 am

1 stop12h 26m

Chicago O'Hare Intl

Wed 4/30

6:45 am-2:10 pm

1 stop12h 25m

$531

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 9/5

8:05 am-12:30 am

1 stop11h 25m

Chicago Midway

Mon 9/8

9:10 pm-10:20 am

1 stop18h 10m

$558

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 5/4

2:40 pm-8:40 am

1 stop13h 00m

Chicago Midway

Thu 5/8

9:16 am-8:34 pm

2 stops16h 18m

$566

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 5/21

6:20 am-11:59 pm

1 stop12h 39m

Chicago O'Hare Intl

Wed 5/28

3:15 pm-9:11 pm

1 stop10h 56m

$584

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 9/5

9:10 pm-5:55 pm

2 stops15h 45m

Chicago O'Hare Intl

Mon 9/8

6:55 pm-10:20 am

2 stops20h 25m

$590

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 6/27

7:00 am-6:15 am

1 stop18h 15m

Chicago O'Hare Intl

Tue 2/3

6:30 am-5:12 pm

1 stop14h 42m

$684

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sat 8/16

9:15 pm-2:13 pm

1 stop11h 58m

Chicago O'Hare Intl

Mon 8/18

7:00 am-1:45 pm

1 stop11h 45m

$705

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 5/5

9:35 pm-6:01 pm

1 stop15h 26m

$280

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 6/8

9:20 pm-3:50 pm

1 stop13h 30m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 16 results
1
2

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 April 4, 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 April 4, 2025.

The most flights from zzFUW to CHI are scheduled on a Wednesday (4 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 April 4, 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
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,837 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,353 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,837 reviews

Entertainment

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $280. However, be on the lookout for offers from American Airlines 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: United Airlines (85%), Air New Zealand (83%), Avianca( 82%).

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

    While on average a flight from O'ahu to Chicago is generally $2,634, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $512 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 5 airlines flying from O'ahu to Chicago

Discover the top 5 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$291Average$791FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$418Average$711FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$421Average$668FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$444Average$725FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$784Average$1,081FlexibilityNo cancel feeOn-time69%

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