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$279+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap 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 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$455
(Delta)

One-way from

$279
(Alaska Airlines)

Popular in

June

Cheapest in

October

Average price

$736

Good round-trip deal

$634 or less

Good one-way deal

$386 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
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From O'ahu to Chicago (CHI)
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One-way flight from O'ahu to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($112 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from O'ahu to Chicago (CHI).
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Price to beat on a one-way flight from O'ahu to Chicago (CHI).
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Find 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 20, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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 3/55:05 pmHNL - MDW
1 stop13h 07mDelta
Mon 3/106:00 amMDW - HNL
1 stop13h 19mDelta
Deal found 2/19$455
This Delta deal was found by Cheapflights users on 2/19. 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 3/58:15 amHNL - ORD
1 stop11h 41mDelta
Mon 3/106:45 amORD - HNL
1 stop12h 24mDelta
Deal found 2/19$455
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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.
Mon 3/34:20 pmHNL - ORD
2 stops21h 40mAlaska Airlines
Thu 3/67:45 amORD - HNL
1 stop19h 10mAlaska Airlines
Deal found 2/18$505
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/299:39 pmHNL - ORD
1 stop14h 45mAmerican Airlines
Tue 5/67:25 amORD - HNL
1 stop16h 53mAmerican Airlines
Deal found 2/19$523
This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/310:35 pmHNL - MDW
1 stop25h 48mMultiple Airlines
Tue 4/88:50 pmMDW - HNL
1 stop13h 10mMultiple Airlines
Deal found 2/19$541
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/712:10 pmHNL - ORD
3 stops46h 49mMultiple Airlines
Mon 4/212:58 pmORD - HNL
3 stops36h 42mMultiple Airlines
Deal found 2/20$577
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 5/811:15 amHNL - MDW
1 stop13h 05mSouthwest
Sun 5/1110:20 pmMDW - HNL
1 stop16h 45mSouthwest
Deal found 2/19$585
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/19:00 pmHNL - ORD
2 stops12h 05mSouthwest
Mon 5/55:25 pmORD - HNL
2 stops21h 40mSouthwest
Deal found 2/18$596
This Hawaiian Airlines deal was found by Cheapflights users on 2/19. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/58:00 amHNL - ORD
1 stop11h 59mHawaiian Airlines
Mon 3/1010:00 amORD - HNL
1 stop14h 43mHawaiian Airlines
Deal found 2/19$610
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:00 amHNL - ORD
1 stop23h 46mUnited Airlines
Tue 10/216:00 amORD - HNL
1 stop15h 12mUnited Airlines
Deal found 2/19$634

Find flights from O'ahu to Chicago within your budget

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 20, 2025.

Fly from

O'ahu

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/5

5:05 pm-10:12 am

1 stop13h 07m

Chicago Midway

Mon 3/10

6:00 am-2:19 pm

1 stop13h 19m

$455

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 3/5

8:15 am-11:56 pm

1 stop11h 41m

Chicago O'Hare Intl

Mon 3/10

6:45 am-2:09 pm

1 stop12h 24m

$455

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/3

4:20 pm-6:00 pm

2 stops21h 40m

Chicago O'Hare Intl

Thu 3/6

7:45 am-10:55 pm

1 stop19h 10m

$505

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/29

9:39 pm-5:24 pm

1 stop14h 45m

Chicago O'Hare Intl

Tue 5/6

7:25 am-7:18 pm

1 stop16h 53m

$523

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/3

10:35 pm-5:23 am

1 stop25h 48m

Chicago Midway

Tue 4/8

8:50 pm-5:00 am

1 stop13h 10m

$541

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 4/7

12:10 pm-3:59 pm

3 stops46h 49m

Chicago O'Hare Intl

Mon 4/21

2:58 pm-10:40 pm

3 stops36h 42m

$577

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 5/8

11:15 am-5:20 am

1 stop13h 05m

Chicago Midway

Sun 5/11

10:20 pm-10:05 am

1 stop16h 45m

$585

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 5/1

9:00 pm-2:05 pm

2 stops12h 05m

Chicago O'Hare Intl

Mon 5/5

5:25 pm-10:05 am

2 stops21h 40m

$596

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 3/5

8:00 am-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Mon 3/10

10:00 am-7:43 pm

1 stop14h 43m

$610

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 6/3

11:25 pm-5:29 am

1 stop25h 04m

Chicago O'Hare Intl

Tue 7/29

4:48 pm-9:59 am

1 stop22h 11m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 19 results
1
2

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.

Travel insights for flights from O'ahu to Chicago

Get recent, data-driven insights about flights from O'ahu to Chicago including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $321). 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 20, 2025.

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.

Weekly flight availability from O'ahu to Chicago

Explore weekly flight availability from O'ahu to Chicago. 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 February 20, 2025.

The most flights from zzFUW to CHI are scheduled on a Thursday (4 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from O'ahu to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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

    The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $279. However, be on the lookout for offers from American Airlines and Southwest, 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?

    While some choose either Honolulu - Chicago Midway or Honolulu - Chicago Greater Rockford, Honolulu - Chicago O'Hare Intl is the most popular route 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: Air New Zealand (88%), Avianca (88%), United Airlines( 80%).

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

    While on average a flight from O'ahu to Chicago is generally $1,498, our data shows the cheapest flight currently is $258. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $455 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 March is currently the most expensive (average of $321). 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 O'ahu?

Book flights to O'ahu if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 5 airlines flying from O'ahu to Chicago

Discover the top 5 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$291Average$792FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$418Average$617FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$421Average$723FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$444Average$725FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$786Average$1,085FlexibilityNo cancel feeOn-time69%
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