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$244+ Cheap flights from Chicago (CHI) to Honolulu (HNL)

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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Honolulu are usually found in February or January, booked 44 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Chicago to Honolulu

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Honolulu (HNL). 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 julio 31, 2025.

Round-trip from

$472
(Alaska Airlines)

One-way from

$244
(Alaska Airlines)

Popular in

December

Cheapest in

February

Average price

$866

Good round-trip deal

$938 or less

Good one-way deal

$502 or less
From Chicago (CHI) to Honolulu
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One-way flight from Chicago (CHI) to Honolulu
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Highest demand for flights based on searches. 4% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Honolulu.
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Price to beat on a one-way flight from Chicago (CHI) to Honolulu.
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Find flight deals from Chicago to Honolulu

Cheapest flights from Chicago to Honolulu
Explore the most affordable flight options available from Chicago to Honolulu. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/28. 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. 11/69:20 amORD - HNL
2 stops18h 05mAlaska Airlines
lun. 11/1012:40 pmHNL - ORD
1 stop26h 19mAlaska Airlines
Deal found 7/28$471
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.
sáb. 9/208:52 amORD - HNL
2 stops16h 38mDelta
sáb. 9/271:00 pmHNL - ORD
2 stops14h 25mDelta
Deal found 7/29$474
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.
mié. 9/179:20 amMDW - HNL
2 stops16h 10mDelta
mié. 9/244:10 pmHNL - MDW
2 stops15h 18mDelta
Deal found 7/29$474
This Southwest deal was found by Cheapflights users on 7/31. 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. 9/171:35 pmMDW - HNL
1 stop12h 25mSouthwest
mar. 9/239:10 pmHNL - MDW
1 stop16h 55mSouthwest
Deal found 7/31$475
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.
mar. 9/211:45 amORD - HNL
1 stop14h 49mAmerican Airlines
mar. 9/911:02 pmHNL - ORD
1 stop11h 49mAmerican Airlines
Deal found 7/30$481

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Honolulu 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 Chicago to Honolulu that are best for you.

Fly from

Chicago

Fly to

Honolulu

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar. 10/7

8:20 am-10:22 pm

2 stops19h 02m

Honolulu

lun. 10/13

11:37 pm-6:59 pm

2 stops14h 22m

$472

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sáb. 9/20

8:52 am-8:30 pm

2 stops16h 38m

Honolulu

sáb. 9/27

1:00 pm-8:25 am

2 stops14h 25m

$474

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mié. 9/17

9:20 am-8:30 pm

2 stops16h 10m

Honolulu

mié. 9/24

4:10 pm-12:28 pm

2 stops15h 18m

$474

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mié. 9/17

1:35 pm-9:00 pm

1 stop12h 25m

Honolulu

mar. 9/23

9:10 pm-7:05 pm

1 stop16h 55m

$475

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar. 9/2

11:45 am-9:34 pm

1 stop14h 49m

Honolulu

mar. 9/9

11:02 pm-3:51 pm

1 stop11h 49m

$481

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

lun. 9/15

6:55 pm-10:20 am

2 stops20h 25m

Honolulu

lun. 9/22

9:00 pm-2:25 pm

1 stop12h 25m

$526

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

lun. 10/27

7:59 pm-3:33 pm

2 stops24h 34m

$244

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

dom. 10/5

10:15 pm-10:20 am

1 stop17h 05m

$250

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sáb. 8/30

7:15 am-8:28 pm

2 stops18h 13m

$257

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mar. 10/14

9:35 am-8:26 pm

2 stops15h 51m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 16 results
1
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The best insider tips for Chicago to Honolulu flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Honolulu trip
Airports
ORD

For a quick snack before your flight, grab some Garrett Popcorn near gate B8, a Chicago favorite.

Read more about ORDby Ramsey Qubein
HNL

For a quick ride to Waikiki, consider rideshare apps. They're often cheaper and faster than taxis.

Read more about HNLby Yulia Denisyuk
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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 Denisyuk

Yulia Denisyuk

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

Best time to book a flight from Chicago to Honolulu

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Honolulu. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Honolulu, you should look to book at least 44 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Honolulu (average of $469). Flying from Chicago to Honolulu in June is currently the most expensive (average of $687). 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 CHI to HNL?

Find hourly flight availability from Chicago to Honolulu. 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.

A simple way to save on the total cost of your ticket is to fly from Chicago to Honolulu in the afternoon. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago to Honolulu?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Honolulu. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Honolulu flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Honolulu

Explore weekly flight availability from Chicago to Honolulu. 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 CHI to HNL are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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

What’s the top layover airport for flights from Chicago to Honolulu?

Share of 1-stop round-trip flights from Chicago to Honolulu chosen by Cheapflights users in the past 12 months, using the same layover each way.

Seattle (SEA) – chosen by Cheapflights users on 71% of 1-stop itineraries from Chicago to Honolulu on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Honolulu?

Average round-trip fare for 1-stop flights from Chicago to Honolulu, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Seattle (SEA) is the most affordable 1-stop option, with an average round-trip price of $550.

What’s the fastest layover option from Chicago to Honolulu?

Shortest average travel time for 1-stop one-way flights from Chicago to Honolulu, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Portland (PDX) have the shortest average one-way travel time for 1-stop routes: 11h 17m.

Which airport typically offers the quickest layover for flights from Chicago to Honolulu?

Average layover duration for 1-stop one-way flights from Chicago to Honolulu, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Portland (PDX) offer the fastest connection on this route, with an average layover time of 1h 07m.

Reviews of airlines servicing Honolulu

Get insights into the airlines that provide service to Honolulu. 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 Honolulu. Reviews last updated julio 31, 2025.
Read through reviews of airlines operating flights from Chicago to Honolulu, 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
10,000 reviews

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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

Food

7.1

Overall

8.0

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

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 Chicago to Honolulu. 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 into for flights to Honolulu from Chicago?

    Honolulu (HNL) is the airport you will fly into if you book a flight from Chicago to Honolulu. You should not have trouble finding flights to Honolulu from Chicago; the airport handles an average of 2 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the Honolulu airport from Chicago. It is only a 4.4 mi journey from Honolulu (HNL) to Honolulu’s city center.

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

    According to our current data, Alaska Airlines ($472), Delta ($474), and Southwest ($475) offers the cheapest pricing from Chicago to Honolulu. Alaska Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest airlines for a one-way flight from Chicago to Honolulu are Alaska Airlines ($244), Southwest ($250), and Delta ($257).

  • What are the cheapest flights from Chicago to Honolulu?

    On average you can expect to pay $2,111 for a flight from Chicago to Honolulu. The cheapest flight overall is $412 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $419.

  • Where are the most common layover locations when flying from Chicago to Honolulu?

    The most popular layover on flights from Chicago to Honolulu is Los Angeles. Chicago to Honolulu flights stop in Seattle the next most.

  • What are some popular things to do or see while on a layover in Los Angeles?

    The majority of Los Angeles visitors spend their time at Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live. Hollywood Bowl, Hollywood Walk of Fame, and L.A. Live can be visited by traveling about 12.5 mi, 11.7 mi, and 10.8 mi respectively from Los Angeles. Those looking to explore during their layover in Los Angeles can rent a car from Los Angeles for about $51 per day.

  • What are some popular points of interest to see during a layover in Seattle?

    If you're on a layover in Seattle and looking for things to do, consider visiting Pike Place Market, Space Needle, or Seattle Waterfront. Pike Place Market, Space Needle, and Seattle Waterfront are located about 11.2 mi, 12.0 mi, and 10.9 mi, respectively from Seattle/Tacoma Intl. Those on a layover in Seattle in need of a rental car can book one at Seattle/Tacoma Intl for about $81.

  • Where are the least popular layover locations for Chicago to Honolulu flights?

    Chicago to Honolulu flights have a layover in Detroit least often. Detroit is followed by San Francisco in terms of the least popular layover location on flights from Chicago to Honolulu.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Honolulu (average of $469). Flying from Chicago to Honolulu in June is currently the most expensive (average of $687). 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 Honolulu?

Book flights to Honolulu if you plan to visit one of these locations
Aiea
Kahuku

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Alternative routes for Chicago to Honolulu

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Honolulu

Discover the top 6 airlines that operate flights from Chicago to Honolulu. 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
Hawaiian AirlinesCheapest$361Average$780FlexibilityNo cancel feeOn-time85%
DeltaCheapest$397Average$576FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$420Average$642FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$423Average$682FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$559Average$759FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$772Average$1,123FlexibilityNo cancel feeOn-time69%

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