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$218+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Mar 9 — Mar 161
Mon 3/9
Mon 3/16
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 February 7, 2026.

This Expedia deal was found by Cheapflights users on 2/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:20 am
ORD
-
HNL
1 stop15h 39m
Alaska Airlines
Tue 3/172:40 pm
HNL
-
ORD
1 stop10h 59m
Alaska Airlines
Deal found 2/6$391
This Southwest deal was found by Cheapflights users on 2/5. 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 3/27:55 am
MDW
-
HNL
1 stop12h 35m
Southwest
Mon 3/911:55 am
HNL
-
MDW
1 stop13h 00m
Southwest
Deal found 2/5$391
This Alaska Airlines deal was found by Cheapflights users on 2/6. 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 4/74:10 pm
ORD
-
HNL
1 stop34h 30m
Alaska Airlines
Thu 4/2310:00 pm
HNL
-
ORD
1 stop16h 03m
Alaska Airlines
Deal found 2/6$392
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 4/157:21 pm
ORD
-
HNL
1 stop33h 38m
Multiple Airlines
Mon 4/2012:06 pm
HNL
-
ORD
2 stops13h 40m
Multiple Airlines
Deal found 2/7$395
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 4/137:55 am
ORD
-
HNL
2 stops21h 04m
Multiple Airlines
Thu 4/1611:13 am
HNL
-
ORD
1 stop13h 37m
Multiple Airlines
Deal found 2/4$396
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 4/67:45 pm
ORD
-
HNL
1 stop33h 14m
Multiple Airlines
Tue 4/1410:31 pm
HNL
-
ORD
2 stops26h 00m
Multiple Airlines
Deal found 2/5$397
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 4/286:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Thu 5/77:23 am
HNL
-
ORD
1 stop11h 20m
Multiple Airlines
Deal found 2/6$401
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 4/276:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Wed 5/67:00 am
HNL
-
ORD
1 stop11h 59m
Multiple Airlines
Deal found 2/4$402
This Alaska Airlines deal was found by Cheapflights users on 2/4. 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 4/286:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Tue 5/510:00 pm
HNL
-
ORD
1 stop16h 03m
Multiple Airlines
Deal found 2/4$403
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/26:00 am
ORD
-
HNL
2 stops33h 15m
Multiple Airlines
Tue 3/107:50 am
HNL
-
ORD
1 stop15h 59m
Multiple Airlines
Deal found 2/5$405
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 4/166:00 am
ORD
-
HNL
1 stop22h 59m
Multiple Airlines
Mon 4/2010:31 pm
HNL
-
ORD
1 stop26h 19m
Multiple Airlines
Deal found 2/6$406
This Southwest deal was found by Cheapflights users on 2/5. 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 3/38:15 am
MDW
-
HNL
1 stop16h 45m
Southwest
Tue 3/108:10 am
HNL
-
MDW
1 stop15h 25m
Southwest
Deal found 2/5$413

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 February 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(Expedia)

One-way from

$218
(Delta)

Popular in

June

Cheapest in

February

Average price

$640

Good round-trip deal

$547 or less

Good one-way deal

$326 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. 9% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 7, 2026.
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

Mon 5/4

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Wed 5/13

8:10 am-4:35 am

1 stop15h 25m

$413

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 5/4

9:45 pm-9:50 am

1 stop17h 05m

Honolulu

Mon 5/11

11:55 am-5:25 am

1 stop12h 30m

$423

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/20

12:46 pm-9:20 pm

1 stop13h 34m

Honolulu

Tue 4/28

7:45 pm-11:51 am

1 stop11h 06m

$424

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/21

7:30 am-9:00 pm

2 stops18h 30m

Honolulu

Wed 4/29

11:55 am-5:40 am

2 stops12h 45m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 4/29

6:00 am-8:27 pm

2 stops19h 27m

Honolulu

Thu 5/7

7:23 am-11:43 pm

1 stop11h 20m

$428

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 5/3

5:10 am-1:45 pm

1 stop13h 35m

Honolulu

Thu 5/7

9:30 pm-6:50 pm

2 stops16h 20m

$430

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 4/28

7:00 am-2:38 pm

1 stop12h 38m

Honolulu

Tue 5/5

8:35 pm-6:07 pm

2 stops16h 32m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 4/29

1:23 pm-9:45 pm

2 stops13h 22m

Honolulu

Wed 5/6

3:15 pm-8:43 am

1 stop12h 28m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 3/1

10:50 am-9:00 pm

1 stop14h 10m

Honolulu

Thu 3/5

9:15 am-5:00 am

1 stop15h 45m

$431

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 3/9

7:00 am-3:00 pm

1 stop13h 00m

Honolulu

Tue 3/17

2:40 pm-6:39 am

1 stop10h 59m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 41 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
No data available for this route at this time. Please check back soon.

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 February 7, 2026.
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
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,847 reviews
Alaska Airlines
8.0
Very good
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,162 reviews
Alaska Airlines
8.0
Very good
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,245 reviews
Alaska Airlines
8.0
Very good
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,248 reviews
Alaska Airlines
8.0
Very good
11,847 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 13h. The time it takes to get you to your destination can typically vary by up to 4h 05m. 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 Delta, which is currently one of the cheapest options available, starting at $211. Alaska Airlines flights start at $230 while deals on Hawaiian Airlines start at $231 one-way.

  • 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.

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