O'ahu

$256+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Nov 26 — Dec 31
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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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/59:06 pmORD - HNL
2 stops20h 33mMultiple Airlines
Thu 12/114:16 pmHNL - ORD
1 stop15h 26mMultiple Airlines
Deal found 10/25$500
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 12/46:50 amORD - HNL
1 stop12h 47mMultiple Airlines
Tue 12/92:11 pmHNL - ORD
1 stop11h 53mMultiple Airlines
Deal found 10/26$501
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sun 12/712:59 pmORD - HNL
1 stop21h 33mMultiple Airlines
Wed 12/102:11 pmHNL - ORD
1 stop11h 53mMultiple Airlines
Deal found 10/25$502
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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 12/65:51 pmORD - HNL
1 stop32h 18mAlaska Airlines
Wed 12/1011:59 pmHNL - ORD
1 stop26h 22mAlaska Airlines
Deal found 10/26$503
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 12/35:40 pmORD - HNL
1 stop23h 20mDelta
Tue 12/911:23 pmHNL - ORD
1 stop20h 36mDelta
Deal found 10/26$504
This Alaska Airlines deal was found by Cheapflights users on 10/25. 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 12/63:35 pmORD - HNL
1 stop34h 34mAlaska Airlines
Sat 12/137:00 amHNL - ORD
1 stop19h 21mAlaska Airlines
Deal found 10/25$505
This Delta deal was found by Cheapflights users on 10/26. 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 12/166:00 amORD - HNL
2 stops15h 27mDelta
Thu 1/2210:30 pmHNL - ORD
1 stop10h 52mDelta
Deal found 10/26$506
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 11/139:22 pmORD - HNL
1 stop27h 18mMultiple Airlines
Tue 11/187:43 amHNL - ORD
1 stop19h 45mMultiple Airlines
Deal found 10/26$507
This Alaska Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 11/278:00 amORD - HNL
1 stop31h 10mAlaska Airlines
Wed 12/109:33 pmHNL - ORD
1 stop28h 48mAlaska Airlines
Deal found 10/26$508
This Delta deal was found by Cheapflights users on 10/26. 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 12/27:50 amORD - HNL
2 stops17h 58mDelta
Tue 12/911:23 pmHNL - ORD
1 stop20h 36mDelta
Deal found 10/26$509
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Thu 12/46:50 amORD - HNL
1 stop12h 47mMultiple Airlines
Sat 12/68:00 amHNL - ORD
1 stop12h 13mMultiple Airlines
Deal found 10/25$510
This Alaska Airlines deal was found by Cheapflights users on 10/25. 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 12/28:59 pmORD - HNL
1 stop28h 22mAlaska Airlines
Wed 12/1011:59 pmHNL - ORD
1 stop26h 22mAlaska Airlines
Deal found 10/25$511

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$498
(Alaska Airlines)

One-way from

$256
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$636

Good round-trip deal

$673 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 ($38 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Average for round-trip flights in October 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.

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 October 27, 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

Thu 1/22

7:30 am-9:28 pm

2 stops17h 58m

Honolulu

Sat 1/31

1:55 pm-9:40 am

2 stops15h 45m

$504

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 1/21

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Tue 1/27

4:50 pm-10:01 am

1 stop13h 11m

$527

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 12/10

3:05 pm-9:21 pm

1 stop34h 16m

Honolulu

Mon 12/15

12:40 pm-7:54 pm

1 stop27h 14m

$531

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 11/25

8:49 pm-6:14 pm

2 stops25h 25m

Honolulu

Wed 12/3

11:30 pm-7:54 pm

1 stop16h 24m

$539

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 12/8

7:20 am-8:29 pm

2 stops17h 09m

Honolulu

Thu 12/11

2:45 pm-8:40 am

2 stops13h 55m

$548

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/8

10:30 am-9:00 pm

2 stops14h 30m

Honolulu

Thu 1/15

12:30 pm-5:05 am

2 stops12h 35m

$558

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 1/16

7:30 am-6:29 pm

1 stop14h 59m

Honolulu

Mon 1/19

5:15 pm-1:18 pm

2 stops16h 03m

$558

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 12/10

7:50 am-9:48 pm

2 stops17h 58m

Honolulu

Mon 12/15

4:45 pm-8:04 am

1 stop11h 19m

$558

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 11/27

10:10 am-9:49 pm

2 stops15h 39m

Honolulu

Wed 12/10

11:23 pm-5:15 pm

1 stop13h 52m

$568

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 12/9

7:50 am-9:48 pm

2 stops17h 58m

Honolulu

Sun 12/14

9:33 pm-5:15 pm

2 stops15h 42m

$576

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 37 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, January is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $362). Flying from Chicago to O'ahu in July is currently the most expensive (average of $663). 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 October 27, 2025.

One of the essential ways to save on airfare from Chicago to O'ahu is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 39% on airfare.

What is the cheapest day to fly from Chicago to O'ahu?

Use this chart to determine the cheapest time to fly round-trip from Chicago to O'ahu. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to O'ahu flight should consider departing on Thursday afternoons when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 27, 2025.

The most flights from CHI to zzFUW are scheduled on a Monday (5 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 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 October 27, 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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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.

Crew

8.5

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Overall

8.0

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, Alaska Airlines, and Southwest fly from Chicago to O'ahu in about 14h 30m. The time it takes to get you to your destination can typically vary by up to 19h 46m. 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 Southwest, which is currently one of the cheapest options available, starting at $256. Delta flights start at $257 while deals on Alaska Airlines start at $263 one-way.

  • 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 $2,163, our data indicates the cheapest price to be $286. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $422.

  • 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, January is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $362). Flying from Chicago to O'ahu in July is currently the most expensive (average of $663). 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$295Average$588FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$405Average$742FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$423Average$671FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$440Average$780FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$553Average$757FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$692Average$1,104FlexibilityNo cancel feeOn-time69%

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