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$204+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$486
(Alaska Airlines)

One-way from

$217
(Delta)

Popular in

December

Cheapest in

February

Average price

$867

Good round-trip deal

$922 or less

Good one-way deal

$520 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 ($32 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 July 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 July 25, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/24. 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.
Sun 10/127:59 pmORD - HNL
1 stop30h 06mAlaska Airlines
Fri 10/2410:20 pmHNL - ORD
1 stop20h 39mAlaska Airlines
Deal found 7/24$486
This Delta deal was found by Cheapflights users on 7/24. 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 12/96:00 amORD - HNL
2 stops15h 29mDelta
Mon 12/159:55 pmHNL - ORD
1 stop21h 52mDelta
Deal found 7/24$490
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sun 8/311:40 pmMDW - HNL
1 stop12h 20mSouthwest
Mon 9/811:35 amHNL - MDW
2 stops12h 35mSouthwest
Deal found 7/23$498
This Delta deal was found by Cheapflights users on 7/23. 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 9/46:00 amMDW - HNL
1 stop12h 15mDelta
Mon 9/810:42 pmHNL - MDW
2 stops14h 55mDelta
Deal found 7/23$499
This Hawaiian Airlines deal was found by Cheapflights users on 7/24. 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.
Sun 8/312:07 pmORD - HNL
1 stop11h 43mHawaiian Airlines
Sat 9/67:50 amHNL - ORD
1 stop11h 14mHawaiian Airlines
Deal found 7/24$503
This Kissandfly.com deal was found by Cheapflights users on 7/24. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/77:55 amORD - HNL
1 stop12h 45mMultiple Airlines
Sun 9/1411:09 pmHNL - ORD
2 stops18h 34mMultiple Airlines
Deal found 7/24$542

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 July 25, 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

Sat 9/20

12:05 pm-10:41 pm

2 stops15h 36m

Honolulu

Sat 9/27

7:50 am-12:04 am

1 stop11h 14m

$489

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 10/10

7:30 am-7:20 pm

1 stop16h 50m

Honolulu

Fri 10/17

9:55 pm-5:46 pm

1 stop14h 51m

$493

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 8/31

1:40 pm-9:00 pm

1 stop12h 20m

Honolulu

Mon 9/8

11:35 am-5:10 am

2 stops12h 35m

$498

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/4

6:00 am-1:15 pm

1 stop12h 15m

Honolulu

Mon 9/8

10:42 pm-6:37 pm

2 stops14h 55m

$499

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 9/8

10:00 am-7:07 pm

1 stop14h 07m

Honolulu

Mon 9/22

10:35 am-7:03 am

1 stop15h 28m

$522

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 9/7

7:55 am-3:40 pm

1 stop12h 45m

Honolulu

Sun 9/14

11:09 pm-10:43 pm

2 stops18h 34m

$542

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 10/7

8:20 am-9:05 pm

1 stop17h 45m

$204

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/3

6:00 am-1:15 pm

1 stop12h 15m

$212

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 9/3

1:20 pm-9:32 pm

2 stops13h 12m

$217

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 10/14

9:25 pm-10:20 am

1 stop17h 55m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 14 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 July 25, 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 July 25, 2025.

The most flights from CHI to zzFUW are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, 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 July 25, 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

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,235 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,967 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,595 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,880 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 $217. Alaska Airlines flights start at $249 while deals on Southwest start at $250 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 $2,397, our data indicates the cheapest price to be $386. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $403.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$361Average$784FlexibilityNo cancel feeOn-time85%
DeltaCheapest$380Average$578FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$421Average$644FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$423Average$680FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$559Average$759FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$771Average$1,126FlexibilityNo cancel feeOn-time69%

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