O'ahu

$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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Oct 22 — Oct 291
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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 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$466
(KAYAK)

One-way from

$236
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$670

Good round-trip deal

$747 or less

Good one-way deal

$380 or less
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
From Chicago (CHI) to O'ahu
One-way flight from Chicago (CHI) to O'ahu
Highest demand for flights based on searches. 4% potential increase in price ($40 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in September 2025
Price to beat on a round-trip flight from Chicago (CHI) to O'ahu.
Price to beat on a one-way flight from Chicago (CHI) to O'ahu.

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 22, 2025.

This KAYAK deal was found by Cheapflights users on 9/20. 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 12/69:15 amORD - HNL
1 stop16h 06mAlaska Airlines
Wed 12/109:40 pmHNL - ORD
2 stops12h 29mAlaska Airlines
Deal found 9/20$466
This Aunt Betty deal was found by Cheapflights users on 9/20. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/510:00 amORD - HNL
1 stop14h 04mHawaiian Airlines
Wed 11/1211:55 pmHNL - ORD
1 stop13h 02mHawaiian Airlines
Deal found 9/20$467
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Mon 10/276:45 amORD - HNL
1 stop12h 35mAmerican Airlines
Mon 11/102:36 pmHNL - ORD
1 stop12h 07mAmerican Airlines
Deal found 9/21$475
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/246:45 amORD - HNL
1 stop12h 28mAmerican Airlines
Tue 11/410:55 pmHNL - ORD
1 stop11h 18mAmerican Airlines
Deal found 9/22$477
This Delta deal was found by Cheapflights users on 9/21. 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 10/217:37 amORD - HNL
1 stop16h 32mDelta
Tue 10/2810:31 pmHNL - ORD
1 stop13h 39mDelta
Deal found 9/21$479
This Southwest deal was found by Cheapflights users on 9/22. 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.
Sat 10/251:50 pmMDW - HNL
1 stop12h 15mSouthwest
Fri 10/318:10 amHNL - MDW
1 stop16h 05mSouthwest
Deal found 9/22$479
This Alaska Airlines deal was found by Cheapflights users on 9/22. 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.
Sat 10/253:50 pmORD - HNL
1 stop30h 05mAlaska Airlines
Fri 10/311:40 pmHNL - ORD
1 stop10h 21mAlaska Airlines
Deal found 9/22$481
This Delta deal was found by Cheapflights users on 9/20. 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
Mon 11/104:45 pmHNL - ORD
1 stop13h 16mDelta
Deal found 9/20$483
This Delta deal was found by Cheapflights users on 9/20. 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 10/279:35 amMDW - HNL
2 stops15h 51mDelta
Mon 11/104:45 pmHNL - MDW
1 stop12h 07mDelta
Deal found 9/20$483
This Delta deal was found by Cheapflights users on 9/21. 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 10/305:20 amORD - HNL
1 stop13h 12mDelta
Tue 11/42:20 pmHNL - ORD
2 stops13h 30mDelta
Deal found 9/21$484
This Delta deal was found by Cheapflights users on 9/22. 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 10/259:20 amMDW - HNL
2 stops16h 06mDelta
Fri 10/313:10 pmHNL - MDW
1 stop13h 35mDelta
Deal found 9/22$484
This Alaska Airlines deal was found by Cheapflights users on 9/20. 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 12/97:59 pmORD - HNL
2 stops25h 51mAlaska Airlines
Wed 12/178:13 amHNL - ORD
1 stop11h 37mAlaska Airlines
Deal found 9/20$486

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 22, 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

Mon 11/3

7:10 am-2:51 pm

1 stop11h 41m

Honolulu

Sun 11/9

5:15 pm-12:39 pm

1 stop15h 24m

$479

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 11/10

9:30 pm-11:20 am

1 stop17h 50m

Honolulu

Mon 11/17

9:25 pm-1:40 pm

1 stop12h 15m

$479

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 11/2

7:45 am-4:15 pm

1 stop12h 30m

Honolulu

Thu 11/6

9:55 pm-4:40 pm

1 stop14h 45m

$479

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 10/27

9:35 am-8:26 pm

2 stops15h 51m

Honolulu

Mon 11/10

4:45 pm-8:52 am

1 stop12h 07m

$483

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 10/21

7:37 am-7:09 pm

1 stop16h 32m

Honolulu

Tue 10/28

1:20 pm-8:30 am

2 stops14h 10m

$484

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 11/18

5:00 am-3:00 pm

2 stops14h 00m

Honolulu

Mon 11/24

9:55 pm-2:10 pm

1 stop12h 15m

$484

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 10/28

7:50 am-1:22 pm

1 stop10h 32m

Honolulu

Sun 11/2

2:20 pm-7:50 am

2 stops13h 30m

$484

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 12/4

6:45 am-8:28 pm

2 stops17h 43m

Honolulu

Sun 12/14

11:35 pm-5:18 pm

1 stop13h 43m

$484

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 10/31

5:20 am-1:32 pm

1 stop13h 12m

Honolulu

Sun 11/2

2:20 pm-7:50 am

2 stops13h 30m

$484

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 11/5

7:37 am-8:09 pm

1 stop16h 32m

Honolulu

Wed 11/12

11:25 pm-6:45 pm

2 stops15h 20m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

Showing 1-10 of 40 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 22, 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 22, 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 22, 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.

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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.

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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.

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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.
8.0
Very good

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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.

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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.

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Entertainment

7.0

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 Delta and Southwest fly from Chicago to O'ahu in about 11h 41m. The time it takes to get you to your destination can typically vary by up to 6h 09m. The distance between Chicago and O'ahu is about 4234 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 $2,162, 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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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 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$326Average$584FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$405Average$744FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$420Average$669FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$425Average$755FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$553Average$757FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$735Average$1,107FlexibilityNo cancel feeOn-time69%

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