HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$257+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'ahu to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from O'ahu to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from O'ahu (zzFUW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 17, 2025.

Round-trip from

$427
(Trip.com)

One-way from

$257
(Delta)
From O'ahu to Chicago (CHI)
Search Deals
One-way flight from O'ahu to Chicago (CHI)
Search Deals

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 January 17, 2025.

This Trip.com deal was found by Cheapflights users on 1/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/64:56 pmHNL - ORD
1 stop19h 31mAlaska Airlines
Mon 2/107:45 amORD - HNL
1 stop19h 14mAlaska Airlines
Deal found 1/16$427
This Delta deal was found by Cheapflights users on 1/15. 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 2/198:46 pmHNL - ORD
1 stop11h 59mDelta
Mon 2/245:45 amORD - HNL
1 stop13h 11mDelta
Deal found 1/15$433
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/65:05 pmHNL - MDW
1 stop13h 07mDelta
Mon 2/1010:19 amMDW - HNL
2 stops15h 37mDelta
Deal found 1/16$439
This Mytrip deal was found by Cheapflights users on 1/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/21:55 pmHNL - ORD
1 stop11h 33mMultiple Airlines
Sun 3/94:45 pmORD - HNL
1 stop22h 25mMultiple Airlines
Deal found 1/16$466
This American Airlines deal was found by Cheapflights users on 1/15. 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 2/1810:41 pmHNL - ORD
1 stop13h 06mAmerican Airlines
Wed 2/262:13 pmORD - HNL
1 stop12h 28mAmerican Airlines
Deal found 1/15$523
This Kissandfly.com deal was found by Cheapflights users on 1/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/211:34 pmHNL - MDW
3 stops20h 43mMultiple Airlines
Sun 3/95:20 amMDW - HNL
2 stops20h 35mMultiple Airlines
Deal found 1/16$560
This Southwest deal was found by Cheapflights users on 1/15. 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 3/183:15 pmHNL - ORD
2 stops20h 10mSouthwest
Tue 3/256:00 amORD - HNL
2 stops15h 00mSouthwest
Deal found 1/15$614
This Southwest deal was found by Cheapflights users on 1/15. 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 3/183:15 pmHNL - MDW
2 stops18h 50mSouthwest
Tue 3/259:35 pmMDW - HNL
1 stop17h 40mSouthwest
Deal found 1/15$623
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/187:00 amHNL - ORD
1 stop24h 52mUnited Airlines
Tue 4/228:45 amORD - HNL
1 stop15h 36mUnited Airlines
Deal found 1/14$663

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 2/6

4:56 pm-4:27 pm

1 stop19h 31m

Chicago O'Hare Intl

Mon 2/10

7:45 am-10:59 pm

1 stop19h 14m

$427

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 2/19

8:46 pm-12:45 pm

1 stop11h 59m

Chicago O'Hare Intl

Wed 2/26

7:00 am-4:58 pm

1 stop13h 58m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 2/6

5:05 pm-10:12 am

1 stop13h 07m

Chicago Midway

Mon 2/10

10:19 am-9:56 pm

2 stops15h 37m

$439

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 3/2

1:55 pm-5:28 am

1 stop11h 33m

Chicago O'Hare Intl

Sun 3/9

4:45 pm-10:10 am

1 stop22h 25m

$466

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 2/18

10:41 pm-3:47 pm

1 stop13h 06m

Chicago O'Hare Intl

Sun 2/23

8:05 am-3:55 pm

1 stop11h 50m

$523

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Sun 3/2

11:34 pm-12:17 am

3 stops20h 43m

Chicago Midway

Sun 3/9

5:20 am-8:55 pm

2 stops20h 35m

$560

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 3/18

3:15 pm-4:25 pm

2 stops20h 10m

Chicago O'Hare Intl

Tue 3/25

6:00 am-4:00 pm

2 stops15h 00m

$614

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Tue 3/18

3:15 pm-3:05 pm

2 stops18h 50m

Chicago Midway

Tue 3/25

9:35 pm-10:15 am

1 stop17h 40m

$623

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 4/18

7:00 am-12:52 pm

1 stop24h 52m

Chicago O'Hare Intl

Tue 4/22

8:45 am-7:21 pm

1 stop15h 36m

$663

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 2/17

6:16 pm-12:01 pm

1 stop13h 45m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 18 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 $320). 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 January 17, 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 January 17, 2025.

The most flights from zzFUW to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 January 17, 2025.
Read reviews from past customers who have flown United Airlines, 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
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,320 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,199 reviews
Southwest
8.1
Very good
4,659 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Delta, with whom users have recently found tickets for as low as $257. However, be on the lookout for offers from American 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?

    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: Avianca (95%), Air New Zealand (95%), United Airlines( 91%).

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

    While on average a flight from O'ahu to Chicago is generally $1,242, our data shows the cheapest flight currently is $281. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $433 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 $320). 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

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 4 airlines flying from O'ahu to Chicago

Discover the top 4 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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$301Average$796FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$421Average$725FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$458Average$736FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$786Average$1,085FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.