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$236+ Cheap flights from Chicago (CHI) to O'ahu

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to O'ahu

Keep the following information in mind while searching for Chicago to O'ahu flight deals. Data was last updated September 17, 2025.

Round-trip from

$463
(KAYAK)

One-way from

$236
(Delta)

Popular in

December

Cheapest in

October

Average price

$670

Good round-trip deal

$754 or less

Good one-way deal

$386 or less
From Chicago (CHI) to O'ahu
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One-way flight from Chicago (CHI) to O'ahu
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Highest demand for flights based on searches. 4% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 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 Chicago (CHI) to O'ahu.
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Price to beat on a one-way flight from Chicago (CHI) to O'ahu.
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Find flight deals from Chicago to O'ahu

Cheapest flights from Chicago to O'ahu
Explore the most affordable flight options available from Chicago to O'ahu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:00 amORD - HNL
1 stop15h 05mAlaska Airlines
Fri 12/1211:30 pmHNL - ORD
1 stop10h 39mAlaska Airlines
Deal found 9/15$463
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 11/47:37 amORD - HNL
1 stop16h 32mDelta
Tue 11/1811:28 pmHNL - ORD
1 stop13h 50mDelta
Deal found 9/16$466
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.
Sat 11/157:47 amORD - HNL
1 stop16h 28mDelta
Fri 12/511:35 pmHNL - ORD
1 stop20h 24mDelta
Deal found 9/16$469
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/272:54 pmORD - HNL
1 stop31h 01mAlaska Airlines
Wed 11/57:45 pmHNL - ORD
2 stops20h 10mAlaska Airlines
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.
Thu 10/307:37 amORD - HNL
1 stop16h 32mDelta
Tue 11/411:32 pmHNL - ORD
1 stop13h 38mDelta
Deal found 9/16$472
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.
Sat 11/157:47 amORD - HNL
1 stop16h 28mDelta
Wed 12/311:35 pmHNL - ORD
1 stop13h 43mDelta
Deal found 9/16$474
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.
Mon 10/277:50 amORD - HNL
2 stops16h 19mDelta
Wed 11/52:20 pmHNL - ORD
2 stops15h 23mDelta
Deal found 9/16$476
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 10/286:00 amMDW - HNL
2 stops18h 09mDelta
Thu 11/62:20 pmHNL - MDW
2 stops14h 35mDelta
Deal found 9/16$476
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.
Mon 11/105:32 amORD - HNL
1 stop13h 30mDelta
Mon 11/1711:28 pmHNL - ORD
2 stops15h 17mDelta
Deal found 9/16$478
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:00 amORD - HNL
1 stop11h 20mAlaska Airlines
Fri 11/72:15 pmHNL - ORD
1 stop12h 07mAlaska Airlines
Deal found 9/16$479
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.
Mon 10/279:25 pmMDW - HNL
1 stop17h 55mSouthwest
Wed 11/59:55 pmHNL - MDW
1 stop14h 45mSouthwest
Deal found 9/16$479
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/13:14 pmORD - HNL
1 stop13h 32mAmerican Airlines
Sat 11/810:45 pmHNL - ORD
1 stop10h 32mAmerican Airlines
Deal found 9/16$480

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to O'ahu 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 Chicago to O'ahu that are best for you.

Fly from

Chicago

Fly to

O'ahu

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 10/28

7:59 pm-12:22 pm

1 stop21h 23m

Honolulu

Wed 11/5

11:51 pm-11:59 pm

1 stop20h 08m

$469

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 11/1

7:37 am-8:26 pm

2 stops17h 49m

Honolulu

Sun 11/9

11:28 pm-5:18 pm

1 stop13h 50m

$471

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 10/26

7:37 am-7:09 pm

1 stop16h 32m

Honolulu

Sun 11/2

11:32 pm-6:41 pm

2 stops15h 09m

$471

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 11/1

7:37 am-8:26 pm

2 stops17h 49m

Honolulu

Sat 11/8

11:32 pm-5:18 pm

1 stop13h 46m

$471

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 10/30

7:37 am-7:09 pm

1 stop16h 32m

Honolulu

Tue 11/4

11:32 pm-5:10 pm

1 stop13h 38m

$472

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 12/8

8:20 am-9:00 pm

1 stop16h 40m

Honolulu

Fri 12/12

8:00 am-1:30 am

1 stop13h 30m

$479

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 10/21

7:37 am-7:09 pm

1 stop16h 32m

Honolulu

Fri 10/31

4:50 pm-9:12 am

1 stop11h 22m

$479

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 11/6

7:37 am-8:09 pm

1 stop16h 32m

Honolulu

Tue 11/11

11:28 pm-5:18 pm

1 stop13h 50m

$479

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 10/25

7:37 am-7:09 pm

1 stop16h 32m

Honolulu

Sat 11/1

1:25 pm-9:30 am

2 stops15h 05m

$484

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 11/12

7:33 am-8:15 pm

2 stops16h 42m

Honolulu

Mon 11/17

11:28 pm-5:18 pm

1 stop13h 50m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 36 results
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Best time to book a flight from Chicago to O'ahu

Have a flexible travel schedule? Discover the best time to fly to O'ahu from Chicago 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 Chicago to O'ahu

What is the cheapest month to book a flight from Chicago to O'ahu?

Currently, November is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $469). Flying from Chicago to O'ahu in June is currently the most expensive (average of $687). 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 CHI to FUW?

Find hourly flight availability from Chicago to O'ahu. 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.

When flying from Chicago to O'ahu, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to O'ahu

Explore weekly flight availability from Chicago to O'ahu. 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 CHI to zzFUW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing O'ahu

Get insights into the airlines that provide service to O'ahu. 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 O'ahu. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Chicago to O'ahu, such as Alaska Airlines, Southwest, and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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

Entertainment

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.1

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 Chicago to O'ahu. 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 Chicago to O'ahu?

    Airlines like Alaska Airlines, Delta, and Southwest fly from Chicago to O'ahu in about 16h 40m. The time it takes to get you to your destination can typically vary by up to 4h 43m. The distance between Chicago and O'ahu is about 4243 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $240. Alaska Airlines flights start at $240 while deals on Southwest start at $240 one-way.

  • What are the most reliable airlines from Chicago to O'ahu?

    Consider United Airlines (63%), Air New Zealand (63%) or Qantas Airways (0%) when booking your flight. These represent the most reliable airlines when flying from Chicago to O'ahu.

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

    Looking for the cheapest flight from Chicago to O'ahu? While on average our users pay $2,166, our data indicates the cheapest price to be $326. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $466.

  • Can I find deals for flights from Chicago to O'ahu that include hotel bookings?

    Yes. In addition to deals on Chicago to O'ahu flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to O'ahu?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to O'ahu.

  • Can I find deals for business class flights from Chicago to O'ahu?

    Yes. Cheapflights offers flight deals from Chicago to O'ahu 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 Chicago to O'ahu?

    Currently, November is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $469). Flying from Chicago to O'ahu in June is currently the most expensive (average of $687). 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

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Alternative routes for Chicago to O'ahu

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to O'ahu

Discover the top 6 airlines that operate flights from Chicago to O'ahu. 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$330Average$583FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$405Average$747FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$420Average$666FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$423Average$752FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$553Average$757FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$738Average$1,109FlexibilityNo cancel feeOn-time69%

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