Chicago

$171+ Cheap flights from O'ahu to Chicago (CHI)

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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Mar 11 — Mar 181
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Cheap flight deals from O'ahu to Chicago

Cheapest flights from O'ahu to Chicago
Explore the most affordable flight options available from O'ahu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.

This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:05 pm
HNL
-
ORD
Nonstop8h 09m
United Airlines
Wed 3/1112:50 pm
ORD
-
HNL
1 stop12h 26m
United Airlines
Deal found 2/7$372
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Fri 3/68:00 am
HNL
-
ORD
1 stop12h 58m
United Airlines
Sun 3/89:40 am
ORD
-
HNL
Nonstop9h 24m
United Airlines
Deal found 2/8$388
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.
Thu 4/3010:00 pm
HNL
-
ORD
1 stop16h 03m
Multiple Airlines
Wed 5/68:50 am
ORD
-
HNL
1 stop16h 36m
Multiple Airlines
Deal found 2/6$394
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
-
ORD
1 stop16h 03m
Alaska Airlines
Wed 5/68:50 am
ORD
-
HNL
2 stops17h 13m
Alaska Airlines
Deal found 2/7$399
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
-
HNL
1 stop11h 25m
Southwest
Deal found 2/6$413
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Fri 2/2711:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Sun 3/18:20 am
ORD
-
HNL
1 stop32h 29m
Multiple Airlines
Deal found 2/8$420
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:55 pm
HNL
-
ORD
1 stop14h 47m
Delta
Wed 3/117:20 am
ORD
-
HNL
2 stops18h 33m
Delta
Deal found 2/7$430
This United Airlines deal was found by Cheapflights users on 2/8. 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.
Wed 4/811:45 am
HNL
-
ORD
1 stop12h 30m
United Airlines
Wed 4/151:18 pm
ORD
-
HNL
1 stop11h 31m
United Airlines
Deal found 2/8$432
This Southwest deal was found by Cheapflights users on 2/8. 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 3/28:05 am
HNL
-
MDW
1 stop12h 20m
Southwest
Mon 3/99:30 pm
MDW
-
HNL
1 stop17h 30m
Southwest
Deal found 2/8$440
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 3/212:55 pm
HNL
-
ORD
1 stop22h 03m
Multiple Airlines
Wed 3/117:40 am
ORD
-
HNL
1 stop18h 30m
Multiple Airlines
Deal found 2/8$442
This Delta deal was found by Cheapflights users on 2/8. 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 3/24:45 pm
HNL
-
MDW
1 stop12h 09m
Delta
Mon 3/99:35 am
MDW
-
HNL
2 stops16h 16m
Delta
Deal found 2/8$487
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:31 pm
HNL
-
MDW
2 stops14h 11m
Delta
Sun 5/109:22 am
MDW
-
HNL
2 stops16h 49m
Delta
Deal found 2/6$495

Find flight deals from O'ahu to Chicago

Keep the following information in mind while searching for O'ahu to Chicago flight deals. Data was last updated February 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$372
(United Airlines)

One-way from

$171
(Southwest)

Popular in

July

Cheapest in

February

Average price

$471

Good round-trip deal

$586 or less

Good one-way deal

$317 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
From O'ahu to Chicago (CHI)
One-way flight from O'ahu to Chicago (CHI)
Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in February 2026
Price to beat on a round-trip flight from O'ahu to Chicago (CHI).
Price to beat on a one-way flight from O'ahu to Chicago (CHI).

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'ahu to Chicago 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 9, 2026.
Use the filters below to find and compare flights from O'ahu to Chicago that are best for you.

Fly from

O'ahu

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 3/6

8:00 am-12:58 am

1 stop12h 58m

Chicago O'Hare Intl

Sun 3/8

9:40 am-2:04 pm

Nonstop9h 24m

$388

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/30

10:00 pm-7:03 pm

1 stop16h 03m

Chicago O'Hare Intl

Wed 5/6

8:50 am-8:26 pm

1 stop16h 36m

$394

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/30

10:00 pm-7:03 pm

1 stop16h 03m

Chicago O'Hare Intl

Wed 5/6

8:50 am-9:03 pm

2 stops17h 13m

$399

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/7

1:00 pm-5:50 am

1 stop11h 50m

Chicago Midway

Sun 5/10

2:40 pm-9:05 pm

1 stop11h 25m

$413

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/14

9:40 pm-2:27 pm

1 stop11h 47m

Chicago O'Hare Intl

Tue 4/21

9:30 am-1:42 pm

Nonstop9h 12m

$451

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/30

4:10 pm-10:09 am

2 stops12h 59m

Chicago O'Hare Intl

Wed 5/6

7:20 am-9:45 pm

2 stops19h 25m

$465

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 4/1

5:24 pm-12:57 pm

1 stop14h 33m

Chicago O'Hare Intl

Wed 4/8

7:10 am-3:02 pm

1 stop12h 52m

$481

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 4/13

7:55 am-6:47 am

1 stop17h 52m

Chicago O'Hare Intl

Sat 4/18

7:21 pm-11:59 pm

1 stop33h 38m

$487

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

4:45 pm-8:54 am

1 stop12h 09m

Chicago Midway

Mon 3/9

9:35 am-8:51 pm

2 stops16h 16m

$487

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/2

4:45 pm-9:41 am

1 stop12h 56m

Chicago O'Hare Intl

Mon 3/9

8:55 am-8:51 pm

2 stops16h 56m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 40 results
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Best time to book a flight from O'ahu to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from O'ahu 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 O'ahu to Chicago

What is the cheapest month to book a flight from O'ahu to Chicago?

Currently, August is the cheapest month in which you can book a flight from O'ahu to Chicago (average of $245). Flying from O'ahu to Chicago in July is currently the most expensive (average of $705). 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 FUW to CHI?

Find hourly flight availability from O'ahu to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 9, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from O'ahu to Chicago as you normally would.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 9, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from O'ahu to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Boarding

8.1

Overall

8.0

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Related info for your journey

Find useful and relevant information for your journey from O'ahu to Chicago. 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 O'ahu to Chicago?

    For as low as $413, United Airlines can have you in Chicago from O'ahu in 11h 50m. There are 4243 mi between O'ahu and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from O'ahu to Chicago one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $215. However, be on the lookout for offers from Hawaiian Airlines and Alaska Airlines, as they are both options that can get you from O'ahu to Chicago for a low price.

  • What are the most popular routes from O'ahu to Chicago?

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

    Before booking your flight to Chicago from O'ahu, check out the most reliable airlines to get you to your destination on time: Avianca (90%), United Airlines (88%), Air New Zealand( 88%).

  • What are the cheapest flights from O'ahu to Chicago?

    While on average a flight from O'ahu to Chicago is generally $1,125, our data shows the cheapest flight currently is $219. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $382 for that flight.

  • Can I find deals for flights from O'ahu to Chicago that include hotel bookings?

    Yes. In addition to deals on O'ahu to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'ahu to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'ahu to Chicago.

  • Can I find deals for business class flights from O'ahu to Chicago?

    Yes. Cheapflights offers flight deals from O'ahu to Chicago 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 O'ahu to Chicago?

    Currently, August is the cheapest month in which you can book a flight from O'ahu to Chicago (average of $245). Flying from O'ahu to Chicago in July is currently the most expensive (average of $705). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from O'ahu to Chicago

Discover the top 6 airlines that operate flights from O'ahu to Chicago. 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 February 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$218Average$583FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$753FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$467Average$773FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$479Average$758FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$500Average$982FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$581Average$783FlexibilityNo cancel feeOn-time63%

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