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$238+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
oct. 10 — oct. 171
ven. 10/10
ven. 10/17
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 septembre 10, 2025.

Round-trip from

$459
(Delta)

One-way from

$238
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$650

Good round-trip deal

$828 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 ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($27 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 septembre 10, 2025.

This Alaska Airlines deal was found by Cheapflights users on 9/10. 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.
sam. 11/89:20 amORD - HNL
1 stop31h 05mAlaska Airlines
ven. 11/149:25 pmHNL - ORD
2 stops12h 29mAlaska Airlines
Deal found 9/10$460
This Delta deal was found by Cheapflights users on 9/9. 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.
lun. 10/67:37 amORD - HNL
1 stop16h 32mDelta
dim. 11/22:20 pmHNL - ORD
2 stops15h 23mDelta
Deal found 9/9$462
This Delta deal was found by Cheapflights users on 9/10. 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.
jeu. 11/139:32 amMDW - HNL
2 stops14h 43mDelta
lun. 11/174:45 pmHNL - MDW
1 stop12h 07mDelta
Deal found 9/10$462
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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.
jeu. 11/1310:00 amORD - HNL
1 stop14h 04mAlaska Airlines
mer. 11/199:25 pmHNL - ORD
2 stops18h 30mAlaska Airlines
Deal found 9/10$464
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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.
jeu. 10/21:01 pmORD - HNL
1 stop14h 02mAlaska Airlines
mer. 10/298:00 amHNL - ORD
1 stop11h 24mAlaska Airlines
Deal found 9/9$467
This Delta deal was found by Cheapflights users on 9/10. 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.
mar. 10/216:08 amORD - HNL
2 stops18h 01mDelta
ven. 10/3110:31 pmHNL - ORD
2 stops13h 19mDelta
Deal found 9/10$468
This Alaska Airlines deal was found by Cheapflights users on 9/9. 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.
ven. 10/33:20 pmORD - HNL
1 stop11h 43mAlaska Airlines
mar. 11/411:51 pmHNL - ORD
1 stop10h 03mAlaska Airlines
Deal found 9/9$470
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
dim. 11/239:38 pmORD - HNL
1 stop17h 52mMultiple Airlines
jeu. 12/44:07 pmHNL - ORD
2 stops18h 41mMultiple Airlines
Deal found 9/10$471
This Delta deal was found by Cheapflights users on 9/9. 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.
mar. 10/218:57 amORD - HNL
2 stops16h 29mDelta
mar. 10/2810:31 pmHNL - ORD
1 stop13h 39mDelta
Deal found 9/9$472
This Delta deal was found by Cheapflights users on 9/9. 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.
mar. 11/46:00 amMDW - HNL
1 stop12h 32mDelta
mar. 11/1111:15 pmHNL - MDW
2 stops15h 03mDelta
Deal found 9/9$472
This Delta deal was found by Cheapflights users on 9/9. 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.
jeu. 10/237:37 amORD - HNL
1 stop16h 32mDelta
mer. 11/58:00 amHNL - ORD
2 stops19h 50mDelta
Deal found 9/9$474
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
dim. 11/25:30 amORD - HNL
1 stop32h 26mMultiple Airlines
sam. 11/811:51 pmHNL - ORD
2 stops44h 24mMultiple Airlines
Deal found 9/10$477

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 septembre 10, 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

MDW - HNL

MDWHNL

Chicago Midway

jeu. 11/13

9:30 pm-11:20 am

1 stop17h 50m

Honolulu

mar. 11/18

12:35 pm-5:05 am

2 stops12h 30m

$462

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mer. 11/12

9:32 am-8:15 pm

2 stops14h 43m

Honolulu

lun. 11/17

4:45 pm-8:52 am

1 stop12h 07m

$462

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

sam. 11/15

8:20 am-9:00 pm

1 stop16h 40m

Honolulu

mer. 11/19

9:55 pm-4:20 pm

2 stops14h 25m

$462

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sam. 11/15

10:00 am-8:04 pm

1 stop14h 04m

Honolulu

mer. 11/19

7:45 pm-1:54 pm

2 stops14h 09m

$464

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

lun. 10/27

9:25 pm-10:20 am

1 stop17h 55m

Honolulu

lun. 11/10

9:55 pm-4:20 pm

2 stops14h 25m

$487

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

lun. 10/6

7:37 am-9:25 pm

2 stops18h 48m

Honolulu

mar. 11/4

11:32 pm-5:10 pm

1 stop13h 38m

$521

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

jeu. 11/13

9:32 am-8:15 pm

2 stops14h 43m

Honolulu

mer. 11/19

2:17 pm-9:01 am

2 stops14h 44m

$525

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar. 11/11

9:20 am-12:25 pm

1 stop31h 05m

Honolulu

mar. 11/18

7:45 pm-1:54 pm

2 stops14h 09m

$531

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

jeu. 12/4

9:15 am-9:21 pm

1 stop16h 06m

Honolulu

mar. 12/9

8:13 am-6:54 pm

1 stop30h 41m

$534

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mer. 10/8

6:00 am-7:19 pm

2 stops18h 19m

Honolulu

ven. 10/31

9:30 pm-7:55 pm

2 stops17h 25m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 38 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 septembre 10, 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 septembre 10, 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 septembre 10, 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

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,249 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 Southwest, Delta, and Alaska Airlines fly from Chicago to O'ahu in about 14h 04m. The time it takes to get you to your destination can typically vary by up to 3h 46m. 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 most reliable airlines from Chicago to O'ahu?

    Consider United Airlines (72%), Air New Zealand (72%) 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 $1,959, our data indicates the cheapest price to be $326. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $419.

  • 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 septembre 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$335Average$581FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$405Average$752FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$420Average$663FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$423Average$750FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$553Average$759FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$745Average$1,113FlexibilityNo cancel feeOn-time69%

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