HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$200+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
maj 8 — maj 151
fre 5/8
fre 5/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Honolulu 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.
Cheapflights Tip: The best prices from Honolulu to Chicago are usually found in February or January, booked 26 days in advance, depart on a Monday or Wednesday 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 april 8, 2026.

This Delta deal was found by Cheapflights users on 4/5. 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.
tis 9/19:45 pm
HNL
-
ORD
1 stop10h 45m
Delta
tis 9/87:10 am
ORD
-
HNL
1 stop11h 51m
Delta
Deal found 4/5$424
This Delta deal was found by Cheapflights users on 4/5. 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.
ons 8/129:45 pm
HNL
-
ORD
1 stop14h 37m
Delta
tis 8/187:35 am
ORD
-
HNL
1 stop13h 30m
Delta
Deal found 4/5$454
This Southwest deal was found by Cheapflights users on 4/8. 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.
ons 5/611:10 am
HNL
-
MDW
1 stop13h 15m
Southwest
ons 5/138:55 pm
MDW
-
HNL
1 stop17h 55m
Southwest
Deal found 4/8$475
This Southwest deal was found by Cheapflights users on 4/4. 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.
fre 5/111:05 am
HNL
-
MDW
1 stop13h 55m
Southwest
tis 5/510:05 am
MDW
-
HNL
1 stop15h 55m
Southwest
Deal found 4/4$477
This Alaska Airlines deal was found by Cheapflights users on 4/6. 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.
tors 4/3012:50 pm
HNL
-
ORD
1 stop12h 50m
Alaska Airlines
mån 5/48:50 am
ORD
-
HNL
1 stop13h 42m
Alaska Airlines
Deal found 4/6$477
This United Airlines deal was found by Cheapflights users on 4/5. 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.
tis 5/54:50 pm
HNL
-
ORD
Nonstop8h 11m
United Airlines
tis 5/1211:00 am
ORD
-
HNL
1 stop13h 49m
United Airlines
Deal found 4/5$480
This Southwest deal was found by Cheapflights users on 4/8. 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.
ons 5/68:00 am
HNL
-
MDW
1 stop16h 25m
Southwest
mån 5/118:35 am
MDW
-
HNL
2 stops17h 30m
Southwest
Deal found 4/8$481
This United Airlines deal was found by Cheapflights users on 4/4. 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.
fre 5/11:25 pm
HNL
-
ORD
1 stop11h 15m
United Airlines
tis 5/510:30 am
ORD
-
HNL
1 stop11h 00m
United Airlines
Deal found 4/4$494
This Delta deal was found by Cheapflights users on 4/4. 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.
tors 4/3012:31 pm
HNL
-
ORD
2 stops14h 30m
Delta
ons 5/612:46 pm
ORD
-
HNL
1 stop13h 34m
Delta
Deal found 4/4$500
This Southwest deal was found by Cheapflights users on 4/5. 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.
tis 5/59:25 pm
HNL
-
MDW
1 stop14h 10m
Southwest
tis 5/1211:45 am
MDW
-
HNL
2 stops14h 15m
Southwest
Deal found 4/5$504
This United Airlines deal was found by Cheapflights users on 4/8. 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.
ons 5/61:25 pm
HNL
-
ORD
1 stop11h 15m
United Airlines
mån 5/111:20 pm
ORD
-
HNL
1 stop11h 29m
United Airlines
Deal found 4/8$514
This Southwest deal was found by Cheapflights users on 4/6. 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.
mån 4/278:10 am
HNL
-
MDW
1 stop15h 25m
Southwest
tis 5/1210:05 am
MDW
-
HNL
1 stop15h 55m
Southwest
Deal found 4/6$517

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 april 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$424
(Delta)

One-way from

$200
(Southwest)

Popular in

June

Cheapest in

February

Average price

$683

Good round-trip deal

$688 or less

Good one-way deal

$378 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. 13% potential increase in price ($107 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 april 8, 2026.
Use the filters below to find and compare flights from Honolulu to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

ons 5/6

11:10 am-5:25 am

1 stop13h 15m

Chicago Midway

mån 5/11

9:45 pm-9:50 am

1 stop17h 05m

$500

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

mån 4/27

11:10 am-5:45 am

1 stop13h 35m

Chicago Midway

tis 5/12

10:05 am-9:00 pm

1 stop15h 55m

$517

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tis 4/28

9:25 pm-6:50 pm

2 stops16h 25m

Chicago O'Hare Intl

fre 5/1

8:00 am-9:00 pm

2 stops18h 00m

$595

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tors 4/30

12:50 pm-6:40 am

1 stop12h 50m

Chicago O'Hare Intl

ons 5/6

6:00 am-9:03 pm

1 stop20h 03m

$612

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tors 4/30

8:55 pm-3:30 pm

2 stops13h 35m

Chicago O'Hare Intl

sön 5/3

8:00 am-9:05 pm

2 stops18h 05m

$615

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tis 9/15

4:05 pm-10:24 am

2 stops13h 19m

Chicago O'Hare Intl

tors 10/1

7:35 am-4:05 pm

1 stop13h 30m

$616

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

ons 8/12

9:55 pm-6:57 pm

1 stop16h 02m

Chicago O'Hare Intl

tis 8/18

8:05 pm-10:47 am

1 stop19h 42m

$619

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

tors 4/30

12:31 pm-8:47 am

2 stops15h 16m

Chicago Midway

ons 5/6

6:00 am-1:45 pm

1 stop12h 45m

$625

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tors 5/14

2:45 pm-8:45 am

1 stop13h 00m

Chicago O'Hare Intl

tors 5/28

12:30 pm-9:01 pm

2 stops13h 31m

$625
Quickest round-trip

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

tis 9/8

12:45 pm-6:22 am

1 stop12h 37m

Chicago O'Hare Intl

tors 9/10

2:22 pm-8:30 pm

1 stop11h 08m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/7

Showing 1-10 of 46 resultsSorted by cheapest first
1
2
3
...
5

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 April.
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 April 3, 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 26 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 June is currently the most expensive (average of $587). 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 april 8, 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 april 8, 2026.

The most flights from HNL to CHI are scheduled on a Tuesday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 april 8, 2026.
Read through reviews of airlines operating flights from Honolulu to Chicago, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,338 reviews
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,197 reviews
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,392 reviews
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,554 reviews
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,560 reviews
Southwest
8.0
Very good
4,338 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 4 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 13h. Southwest provides one of the quickest options available for as low as $625. 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 ($230), Hawaiian Airlines ($280), and Alaska Airlines ($467) offers the cheapest pricing from Honolulu to Chicago. Delta is priced at 66% 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 $212 on Delta. Other airlines that offer cheap prices include Hawaiian Airlines from $232 and Southwest from $237 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 (91%), American Airlines (88%) or Alaska Airlines (88%) 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 $286. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $424 on average, our data indicates $1,126 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 June is currently the most expensive (average of $587). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 april 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$230Average$583FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$280Average$594FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$467Average$788FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$479Average$772FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$491Average$938FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$581Average$789FlexibilityNo cancel feeOn-time63%

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.