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$164+ Cheap flights from Honolulu (HNL) 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheapflights Tip: The best prices from Honolulu to Chicago are usually found in February or January, booked 43 days in advance, depart on a Wednesday or Monday and return on a Tuesday

Cheap flight deals from Honolulu to Chicago

Cheapest flights from Honolulu to Chicago
Explore the most affordable flight options available from Honolulu to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 19, 2026.

This Southwest deal was found by Cheapflights users on 2/17. 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.
Fri 4/248:15 am
HNL
-
MDW
1 stop15h 45m
Southwest
Tue 4/2810:05 am
MDW
-
HNL
1 stop15h 55m
Southwest
Deal found 2/17$342
This United Airlines deal was found by Cheapflights users on 2/17. 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.
Thu 4/1611:45 am
HNL
-
ORD
1 stop12h 30m
United Airlines
Tue 4/211:18 pm
ORD
-
HNL
1 stop11h 31m
United Airlines
Deal found 2/17$360
This United Airlines deal was found by Cheapflights users on 2/17. 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 3/117:00 am
HNL
-
ORD
1 stop11h 00m
United Airlines
Tue 3/1712:54 pm
ORD
-
HNL
1 stop12h 27m
United Airlines
Deal found 2/17$370
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/157:50 am
HNL
-
ORD
1 stop17h 00m
Multiple Airlines
Mon 4/209:14 pm
ORD
-
HNL
1 stop17h 45m
Multiple Airlines
Deal found 2/17$376
This United Airlines deal was found by Cheapflights users on 2/17. 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.
Mon 4/277:00 am
HNL
-
ORD
1 stop11h 28m
United Airlines
Sat 5/21:43 pm
ORD
-
HNL
1 stop11h 26m
United Airlines
Deal found 2/17$401
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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.
Wed 9/27:50 am
HNL
-
ORD
1 stop11h 09m
Multiple Airlines
Wed 9/169:20 am
ORD
-
HNL
1 stop11h 30m
Multiple Airlines
Deal found 2/17$408
This Southwest deal was found by Cheapflights users on 2/17. 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 4/148:10 am
HNL
-
MDW
1 stop15h 25m
Southwest
Tue 4/2110:05 am
MDW
-
HNL
1 stop15h 55m
Southwest
Deal found 2/17$411
This Alaska Airlines deal was found by Cheapflights users on 2/17. 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 4/307:23 am
HNL
-
ORD
1 stop11h 20m
Multiple Airlines
Wed 5/66:00 am
ORD
-
HNL
2 stops19h 27m
Multiple Airlines
Deal found 2/17$411
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/301:10 pm
HNL
-
ORD
2 stops38h 40m
Multiple Airlines
Tue 4/147:21 pm
ORD
-
HNL
1 stop30h 26m
Multiple Airlines
Deal found 2/15$416
This United Airlines deal was found by Cheapflights users on 2/17. 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 4/147:00 am
HNL
-
ORD
1 stop11h 28m
United Airlines
Tue 4/2112:55 pm
ORD
-
HNL
1 stop11h 59m
United Airlines
Deal found 2/17$417
This Delta deal was found by Cheapflights users on 2/17. 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 3/113:46 pm
HNL
-
MDW
1 stop12h 07m
Delta
Tue 3/179:35 am
MDW
-
HNL
2 stops16h 18m
Delta
Deal found 2/17$430
This Southwest deal was found by Cheapflights users on 2/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:15 am
HNL
-
MDW
1 stop15h 45m
Southwest
Mon 5/189:45 pm
MDW
-
HNL
1 stop17h 05m
Southwest
Deal found 2/16$431

Find flight deals from Honolulu to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Honolulu (HNL) 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 February 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(Southwest)

One-way from

$164
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$471

Good round-trip deal

$586 or less

Good one-way deal

$310 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From Honolulu to Chicago (CHI)
Search Deals
One-way flight from Honolulu to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 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 Honolulu to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Honolulu to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Honolulu 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 19, 2026.
Use the filters below to find and compare flights from Honolulu to Chicago that are best for you.

Fly from

Honolulu

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 4/24

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Tue 4/28

10:05 am-9:00 pm

1 stop15h 55m

$342

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/30

1:10 pm-8:50 am

2 stops38h 40m

Chicago O'Hare Intl

Tue 4/14

7:21 pm-9:59 am

1 stop19h 38m

$422

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 3/17

7:00 am-11:00 pm

1 stop11h 00m

Chicago O'Hare Intl

Tue 3/24

6:17 am-2:34 pm

1 stop13h 17m

$427

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 4/15

3:15 pm-8:47 am

1 stop12h 32m

Chicago Midway

Mon 4/20

9:29 am-9:20 pm

2 stops16h 51m

$430

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 3/11

3:46 pm-8:53 am

1 stop12h 07m

Chicago Midway

Tue 3/17

9:35 am-8:53 pm

2 stops16h 18m

$430

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 5/8

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Mon 5/18

9:45 pm-9:50 am

1 stop17h 05m

$431

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/7

11:45 am-5:15 am

1 stop12h 30m

Chicago O'Hare Intl

Tue 4/14

9:30 am-1:42 pm

Nonstop9h 12m

$434

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/7

10:40 pm-7:49 pm

2 stops16h 09m

Chicago O'Hare Intl

Tue 4/14

8:50 am-9:20 pm

2 stops17h 30m

$435

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 3/11

7:00 am-11:00 pm

1 stop11h 00m

Chicago O'Hare Intl

Wed 3/18

12:50 pm-8:16 pm

1 stop12h 26m

$437

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 4/27

4:10 pm-10:19 am

2 stops13h 09m

Chicago O'Hare Intl

Sat 5/2

7:00 am-2:40 pm

1 stop12h 40m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 45 results
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Compare providers for flights from Honolulu to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Honolulu to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Honolulu-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Honolulu-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Honolulu-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Honolulu-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Honolulu-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Honolulu to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Honolulu 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 Honolulu to Chicago

How far ahead should I book a flight from Honolulu to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Honolulu to Chicago. Price data was last updated on February 13, 2026.

The price you pay for your flight from Honolulu to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 43 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Honolulu to Chicago?

Currently, August is the cheapest month in which you can book a flight from Honolulu to Chicago (average of $245). Flying from Honolulu 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 HNL to CHI?

Find hourly flight availability from Honolulu 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 19, 2026.

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

Weekly flight availability from Honolulu to Chicago

Explore weekly flight availability from Honolulu 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 19, 2026.

The most flights from HNL to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Honolulu to Chicago?

The best insider tips for Honolulu to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Honolulu to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Yulia Denisyuk

Yulia Denisyuk

Expert on HNL

Yulia is a freelance journalist who’s dispatched from 90+ countries. Her work focuses on cultures, adventure trips and air travel, appearing in NatGeo, NYT, CNTraveler, and more. For past assignments, she’s stayed with nomads in Mongolia and learned the art of Imigongo in Rwanda. She’s based in Chicago; in winter she often questions that decision.

Read more

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 19, 2026.
Read through reviews of airlines operating flights from Honolulu to Chicago, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Alaska Airlines
8.0
Very good
11,904 reviews
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
Delta
7.9
Good
8,212 reviews
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
United Airlines
7.4
Good
9,321 reviews
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.
American Airlines
7.2
Good
11,313 reviews
Alaska Airlines
8.0
Very good
11,904 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Comfort

7.8

Overall

8.0

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 Honolulu to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Honolulu to Chicago?

    Located just 4.4 mi from the city center, Honolulu is the airport most travelers will use when flying to Chicago from Honolulu. Booking flights from Honolulu (HNL) to Chicago should be relatively easy as there are 6 daily outbound flights to Chicago from 6 different airlines.

  • How long is the flight from Honolulu to Chicago?

    A quick flight from Honolulu to Chicago can take about 12h 30m. Southwest provides one of the quickest options available for as low as $360. There are 4234 mi between Honolulu and Chicago. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Honolulu to Chicago round-trip?

    According to our current data, Delta ($218), Hawaiian Airlines ($335), and Alaska Airlines ($467) offers the cheapest pricing from Honolulu to Chicago. Delta is priced at 68% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Honolulu to Chicago one-way?

    One-way options have recently been found by users for as low as $215 on Delta. Other airlines that offer cheap prices include Hawaiian Airlines from $227 and Alaska Airlines from $227 one-way.

  • What are the most popular routes from Honolulu to Chicago?

    Most travelers choose Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway or Honolulu - Chicago Greater Rockford when deciding on the best route from Honolulu to Chicago.

  • What are the most reliable airlines from Honolulu to Chicago?

    Consider United Airlines (93%), Avianca (90%) or Air New Zealand (87%) when booking your flight. These represent the most reliable airlines when flying from Honolulu to Chicago.

  • What are the cheapest flights from Honolulu to Chicago?

    Looking at all options, your cheapest flight can be booked for $241. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $360 on average, our data indicates $1,177 when flying from Honolulu to Chicago.

  • Can I find deals for flights from Honolulu to Chicago that include hotel bookings?

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

  • How can I find direct flights from Honolulu to Chicago?

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

  • Can I find deals for business class flights from Honolulu to Chicago?

    Yes. Cheapflights offers flight deals from Honolulu 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 Honolulu to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Honolulu to Chicago (average of $245). Flying from Honolulu 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 Honolulu to Chicago

Discover the top 6 airlines that operate flights from Honolulu 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 19, 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$961FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$581Average$788FlexibilityNo cancel feeOn-time63%

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