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$247+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
May 18 — May 251
Mon 5/18
Mon 5/25
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 April 18, 2026.

This Southwest deal was found by Cheapflights users on 4/13. 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 5/49:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Fri 5/88:15 am
HNL
-
MDW
1 stop15h 45m
Southwest
Deal found 4/13$434
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/126:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Fri 5/157:24 am
HNL
-
ORD
1 stop11h 31m
Multiple Airlines
Deal found 4/14$457
This Southwest deal was found by Cheapflights users on 4/14. 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 5/58:55 pm
MDW
-
HNL
1 stop17h 55m
Southwest
Tue 5/121:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Deal found 4/14$464
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Mon 5/48:50 am
ORD
-
HNL
1 stop13h 42m
Multiple Airlines
Fri 5/811:59 pm
HNL
-
ORD
1 stop14h 53m
Multiple Airlines
Deal found 4/16$473
This Alaska Airlines deal was found by Cheapflights users on 4/13. 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.
Mon 5/48:50 am
ORD
-
HNL
1 stop13h 42m
Alaska Airlines
Tue 5/127:00 am
HNL
-
ORD
1 stop11h 59m
Alaska Airlines
Deal found 4/13$474
This Southwest deal was found by Cheapflights users on 4/16. 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 8/2410:15 am
MDW
-
HNL
1 stop15h 55m
Southwest
Wed 9/28:10 am
HNL
-
MDW
1 stop15h 20m
Southwest
Deal found 4/16$475
This Southwest deal was found by Cheapflights users on 4/14. 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 8/305:25 am
MDW
-
HNL
1 stop12h 55m
Southwest
Tue 9/89:00 pm
HNL
-
MDW
1 stop11h 35m
Southwest
Deal found 4/14$493
This United Airlines deal was found by Cheapflights users on 4/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:30 am
ORD
-
HNL
Nonstop9h 12m
United Airlines
Thu 5/74:50 pm
HNL
-
ORD
Nonstop8h 11m
United Airlines
Deal found 4/13$495
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Mon 5/48:50 am
ORD
-
HNL
1 stop13h 42m
Multiple Airlines
Mon 5/1111:59 pm
HNL
-
ORD
1 stop11h 57m
Multiple Airlines
Deal found 4/14$496
This Southwest deal was found by Cheapflights users on 4/13. 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 8/2510:20 am
MDW
-
HNL
1 stop15h 50m
Southwest
Tue 9/19:25 pm
HNL
-
MDW
2 stops11h 55m
Southwest
Deal found 4/13$499
This United Airlines deal was found by Cheapflights users on 4/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:30 am
ORD
-
HNL
Nonstop9h 12m
United Airlines
Fri 5/87:00 am
HNL
-
ORD
1 stop11h 28m
United Airlines
Deal found 4/13$504
This United Airlines deal was found by Cheapflights users on 4/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:43 pm
ORD
-
HNL
1 stop11h 26m
United Airlines
Tue 5/191:00 pm
HNL
-
ORD
1 stop11h 06m
United Airlines
Deal found 4/16$514

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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$457
(Kiwi.com)

One-way from

$247
(Southwest)

Popular in

June

Cheapest in

January

Average price

$735

Good round-trip deal

$682 or less

Good one-way deal

$410 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. 12% potential increase in price ($109 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 April 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 April 18, 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

MDW - HNL

MDWHNL

Chicago Midway

Mon 5/4

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Fri 5/8

8:15 am-5:00 am

1 stop15h 45m

$434

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 5/12

9:22 am-9:01 pm

2 stops16h 39m

Honolulu

Tue 5/19

1:50 pm-8:42 am

2 stops13h 52m

$525

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 4/27

10:10 am-9:05 pm

1 stop15h 55m

Honolulu

Mon 5/4

1:00 pm-11:15 am

1 stop17h 15m

$620

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 9/1

7:00 am-1:34 pm

1 stop11h 34m

Honolulu

Wed 9/2

8:00 am-6:22 am

2 stops17h 22m

$645

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 5/3

11:55 am-9:00 pm

2 stops14h 05m

Honolulu

Fri 5/8

11:05 am-5:40 am

2 stops13h 35m

$671

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 5/14

1:20 pm-7:49 pm

1 stop11h 29m

Honolulu

Tue 5/26

2:40 pm-7:16 am

1 stop11h 36m

$680

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/28

7:30 am-9:00 pm

2 stops18h 30m

Honolulu

Sun 5/3

11:10 am-6:00 am

1 stop13h 50m

$680

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 5/13

7:30 am-9:00 pm

2 stops18h 30m

Honolulu

Wed 5/20

9:05 pm-5:55 pm

2 stops15h 50m

$682
Quickest round-trip

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/21

6:10 am-1:05 pm

1 stop11h 55m

Honolulu

Thu 4/23

8:00 am-11:55 pm

1 stop10h 55m

$684

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 9/6

6:00 am-4:22 pm

2 stops15h 22m

Honolulu

Sun 9/13

11:39 pm-7:03 pm

2 stops14h 24m

$700

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 42 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, September is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $232). Flying from Chicago to O'ahu in December is currently the most expensive (average of $2,088). 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 April 18, 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 April 18, 2026.

The most flights from CHI to zzFUW are scheduled on a Friday (5 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 April 18, 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
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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
4,330 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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
12,258 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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
8,424 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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
9,605 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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
11,604 reviews
Southwest
8.0
Very good
4,330 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

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 Southwest, Delta, and United Airlines fly from Chicago to O'ahu in about 11h 29m. The time it takes to get you to your destination can typically vary by up to 5h 36m. 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 (67%), Air New Zealand (67%) 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 $747, our data indicates the cheapest price to be $312. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $473.

  • 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, September is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $232). Flying from Chicago to O'ahu in December is currently the most expensive (average of $2,088). 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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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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$649FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$331Average$641FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$397Average$915FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$423Average$659FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$464Average$817FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$470Average$766FlexibilityNo cancel feeOn-time63%

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