HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$312+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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

Keep the following information in mind while searching for O'ahu to Chicago flight deals. Data was last updated julio 31, 2025.

Round-trip from

$409
(Southwest)

One-way from

$312
(lol.travel)

Popular in

July

Cheapest in

November

Average price

$873

Good round-trip deal

$779 or less

Good one-way deal

$375 or less
From O'ahu to Chicago (CHI)
Search Deals
One-way flight from O'ahu to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from O'ahu to Chicago (CHI).
Search Deals
Price to beat on a 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 julio 31, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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.
jue. 11/68:00 amHNL - MDW
1 stop13h 30mSouthwest
dom. 11/97:45 amMDW - HNL
1 stop12h 30mSouthwest
Deal found 7/29$409
This American Airlines deal was found by Cheapflights users on 7/30. 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.
mié. 9/39:42 pmHNL - ORD
1 stop13h 16mAmerican Airlines
dom. 9/79:50 amORD - HNL
1 stop13h 04mAmerican Airlines
Deal found 7/30$423
This Delta deal was found by Cheapflights users on 7/30. 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.
mié. 9/34:09 pmHNL - ORD
2 stops15h 36mDelta
dom. 9/77:15 amORD - HNL
1 stop12h 04mDelta
Deal found 7/30$429
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
sáb. 9/137:50 amHNL - ORD
1 stop11h 14mHawaiian Airlines
sáb. 9/202:07 pmORD - HNL
1 stop11h 43mHawaiian Airlines
Deal found 7/29$441
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
jue. 11/69:02 amHNL - ORD
2 stops29h 57mAlaska Airlines
dom. 11/99:20 amORD - HNL
1 stop12h 35mAlaska Airlines
Deal found 7/29$443
This Delta deal was found by Cheapflights users on 7/29. 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.
lun. 9/810:06 pmHNL - MDW
2 stops15h 31mDelta
mié. 9/249:20 amMDW - HNL
2 stops16h 10mDelta
Deal found 7/29$504
This Southwest deal was found by Cheapflights users on 7/30. 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.
mié. 9/249:00 pmHNL - ORD
1 stop12h 25mSouthwest
lun. 9/296:55 pmORD - HNL
2 stops20h 25mSouthwest
Deal found 7/30$531

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 julio 31, 2025.
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 - MDW

HNLMDW

Honolulu

jue. 11/6

8:00 am-1:30 am

1 stop13h 30m

Chicago Midway

dom. 11/9

7:45 am-4:15 pm

1 stop12h 30m

$409

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

mié. 9/3

9:42 pm-3:58 pm

1 stop13h 16m

Chicago O'Hare Intl

dom. 9/7

9:50 am-5:54 pm

1 stop13h 04m

$423

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

mié. 9/3

4:09 pm-12:45 pm

2 stops15h 36m

Chicago O'Hare Intl

dom. 9/7

7:15 am-2:19 pm

1 stop12h 04m

$429

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

sáb. 9/13

7:50 am-12:04 am

1 stop11h 14m

Chicago O'Hare Intl

sáb. 9/20

2:07 pm-8:50 pm

1 stop11h 43m

$441

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

jue. 11/6

9:02 am-6:59 pm

2 stops29h 57m

Chicago O'Hare Intl

dom. 11/9

9:20 am-5:55 pm

1 stop12h 35m

$443

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

lun. 9/8

10:06 pm-6:37 pm

2 stops15h 31m

Chicago Midway

mié. 9/24

9:20 am-8:30 pm

2 stops16h 10m

$504

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

mié. 9/24

9:00 pm-2:25 pm

1 stop12h 25m

Chicago O'Hare Intl

lun. 9/29

6:55 pm-10:20 am

2 stops20h 25m

$531

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

mar. 9/30

9:40 pm-7:35 pm

1 stop16h 55m

$312

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

mar. 1/27

4:50 pm-1:04 pm

2 stops16h 14m

$314

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

lun. 1/12

9:55 pm-12:35 pm

1 stop10h 40m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 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.

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 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 julio 31, 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 julio 31, 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).

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 julio 31, 2025.
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.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 United Airlines, with whom users have recently found tickets for as low as $312. However, be on the lookout for offers from Alaska 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: Avianca (95%), United Airlines (95%), Air New Zealand( 95%).

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

    While on average a flight from O'ahu to Chicago is generally $1,696, our data shows the cheapest flight currently is $225. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $423 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$231Average$586FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$335Average$777FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$426Average$741FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$457Average$726FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$606Average$788FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$780Average$1,082FlexibilityNo 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.