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$223+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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Cheap 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 March 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Wed 8/197:00 am
ORD
-
HNL
1 stop11h 40m
Multiple Airlines
Fri 8/287:50 am
HNL
-
ORD
1 stop11h 09m
Multiple Airlines
Deal found 3/19$407
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Tue 4/2112:10 pm
HNL
-
ORD
1 stop20h 03m
Multiple Airlines
Deal found 3/17$410
This Alaska Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 9/28:00 am
ORD
-
HNL
1 stop14h 00m
Multiple Airlines
Tue 9/810:20 pm
HNL
-
ORD
1 stop10h 34m
Multiple Airlines
Deal found 3/18$412
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Tue 4/216:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Wed 4/2912:50 pm
HNL
-
ORD
1 stop12h 50m
Multiple Airlines
Deal found 3/19$420
This Delta deal was found by Cheapflights users on 3/19. 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 4/207:00 am
ORD
-
HNL
1 stop12h 40m
Delta
Wed 4/293:40 pm
HNL
-
ORD
1 stop15h 46m
Delta
Deal found 3/19$424
This Southwest deal was found by Cheapflights users on 3/17. 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 4/209:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Thu 4/308:10 am
HNL
-
MDW
1 stop15h 25m
Southwest
Deal found 3/17$428
This Delta deal was found by Cheapflights users on 3/20. 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.
Tue 9/2212:40 pm
ORD
-
HNL
1 stop11h 41m
Delta
Fri 9/251:30 pm
HNL
-
ORD
2 stops14h 04m
Delta
Deal found 3/20$430
This Delta deal was found by Cheapflights users on 3/17. 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 4/156:00 am
MDW
-
HNL
1 stop12h 45m
Delta
Wed 4/2212:31 pm
HNL
-
MDW
2 stops15h 16m
Delta
Deal found 3/17$430
This Southwest deal was found by Cheapflights users on 3/19. 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.
Tue 4/1410:40 am
MDW
-
HNL
2 stops15h 20m
Southwest
Tue 4/218:00 am
HNL
-
MDW
1 stop16h 25m
Southwest
Deal found 3/19$434
This Delta deal was found by Cheapflights users on 3/19. 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 4/228:50 am
ORD
-
HNL
2 stops17h 30m
Delta
Wed 4/294:10 pm
HNL
-
ORD
2 stops15h 35m
Delta
Deal found 3/19$435
This Delta deal was found by Cheapflights users on 3/19. 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 4/209:29 am
MDW
-
HNL
2 stops16h 51m
Delta
Wed 4/2912:25 pm
HNL
-
MDW
2 stops15h 21m
Delta
Deal found 3/19$435
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Mon 4/136:40 am
ORD
-
HNL
2 stops43h 07m
Multiple Airlines
Mon 4/208:34 pm
HNL
-
ORD
1 stop28h 16m
Multiple Airlines
Deal found 3/17$437

Find 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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(Kiwi.com)

One-way from

$223
(Delta)

Popular in

June

Cheapest in

January

Average price

$767

Good round-trip deal

$652 or less

Good one-way deal

$386 or less
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
Search Deals
From Chicago (CHI) to O'ahu
Search Deals
One-way flight from Chicago (CHI) to O'ahu
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to O'ahu.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to O'ahu.
Search Deals

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 March 22, 2026.
Use the filters below to find and compare flights from Chicago to O'ahu that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/13

7:00 am-2:40 pm

1 stop12h 40m

Honolulu

Wed 4/22

12:25 pm-8:01 am

2 stops14h 36m

$470

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/27

6:00 am-8:27 pm

2 stops19h 27m

Honolulu

Sun 5/3

8:34 pm-7:52 pm

2 stops18h 18m

$620

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/9

6:00 am-2:00 pm

1 stop13h 00m

Honolulu

Thu 4/16

3:15 pm-8:47 am

1 stop12h 32m

$643

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 5/4

8:35 am-9:05 pm

2 stops17h 30m

Honolulu

Tue 6/2

11:55 am-6:00 am

1 stop13h 05m

$647

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 4/19

8:00 am-9:05 pm

2 stops18h 05m

Honolulu

Sun 4/26

8:55 pm-6:50 pm

1 stop16h 55m

$677

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/16

12:10 pm-9:05 pm

2 stops13h 55m

Honolulu

Thu 4/23

8:50 pm-5:55 pm

2 stops16h 05m

$681

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 4/16

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Mon 4/20

8:50 pm-2:15 pm

2 stops12h 25m

$683

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 5/13

12:30 pm-9:01 pm

2 stops13h 31m

Honolulu

Wed 5/20

1:50 pm-8:36 am

2 stops13h 46m

$700

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 5/7

8:50 am-10:28 pm

2 stops18h 38m

Honolulu

Wed 5/13

9:50 pm-11:55 pm

1 stop21h 05m

$703

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 4/13

6:00 am-2:20 pm

2 stops13h 20m

Honolulu

Fri 4/24

9:05 pm-2:45 pm

2 stops12h 40m

$718

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 41 resultsSorted by cheapest first
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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 $310). 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 March 22, 2026.

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 March 22, 2026.

The most flights from CHI to zzFUW are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 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 March 22, 2026.
Read through reviews of airlines operating flights from Chicago to O'ahu, such as Southwest,Alaska Airlines, andDelta. 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.
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,091 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,314 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,455 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,489 reviews
Southwest
8.0
Very good
4,324 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 12h 40m. The time it takes to get you to your destination can typically vary by up to 4h 50m. 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 Southwest, which is currently one of the cheapest options available, starting at $171. Delta flights start at $211 while deals on Alaska Airlines start at $230 one-way.

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

    Consider United Airlines (80%), Air New Zealand (80%) or American Airlines (47%) 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 $1,045, our data indicates the cheapest price to be $220. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $362.

  • 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 $310). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$646FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$331Average$679FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$401Average$931FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$428Average$670FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$465Average$806FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$553Average$765FlexibilityNo cancel feeOn-time63%

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