Hawaii

$181+ Cheap flights from Chicago (CHI) to Hawaii

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Oct 19 — Oct 261
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Cheap flight deals from Chicago to Hawaii

Keep the following information in mind while searching for Chicago to Hawaii flight deals. Data was last updated September 19, 2025.

Round-trip from

$382
(Delta)

One-way from

$181
(Alaska Airlines)

Popular in

December

Cheapest in

October

Average price

$670

Good round-trip deal

$754 or less

Good one-way deal

$386 or less
From Chicago (CHI) to Hawaii
One-way flight from Chicago (CHI) to Hawaii
Highest demand for flights based on searches. 4% potential increase in price ($40 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Average for round-trip flights in September 2025
Price to beat on a round-trip flight from Chicago (CHI) to Hawaii.
Price to beat on a one-way flight from Chicago (CHI) to Hawaii.

Find flight deals from Chicago to Hawaii

Cheapest flights from Chicago to Hawaii
Explore the most affordable flight options available from Chicago to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2025.

This Delta deal was found by Cheapflights users on 9/17. 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 10/227:37 amORD - KOA
1 stop14h 53mDelta
Mon 10/279:30 pmKOA - ORD
1 stop14h 40mDelta
Deal found 9/17$382
This Delta deal was found by Cheapflights users on 9/17. 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 10/87:37 amORD - KOA
2 stops16h 46mDelta
Wed 10/229:30 pmKOA - ORD
1 stop11h 00mDelta
Deal found 9/17$387
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 12/43:05 pmORD - LIH
1 stop26h 48mAlaska Airlines
Thu 12/112:53 pmLIH - ORD
1 stop24h 01mAlaska Airlines
Deal found 9/17$399
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 10/277:37 amORD - KOA
1 stop14h 53mDelta
Fri 10/319:30 pmKOA - ORD
1 stop14h 48mDelta
Deal found 9/17$410
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 11/37:37 amORD - LIH
1 stop16h 28mDelta
Mon 11/109:29 pmLIH - ORD
1 stop15h 49mDelta
Deal found 9/16$410
This Delta deal was found by Cheapflights users on 9/17. 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.
Sun 10/267:37 amORD - LIH
1 stop16h 28mDelta
Sun 11/210:40 pmLIH - ORD
2 stops16h 01mDelta
Deal found 9/17$415
This Alaska Airlines deal was found by Cheapflights users on 9/18. 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 12/47:59 pmORD - LIH
1 stop21h 54mAlaska Airlines
Tue 12/92:53 pmLIH - ORD
1 stop24h 01mAlaska Airlines
Deal found 9/18$421
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:00 amORD - LIH
1 stop11h 18mAmerican Airlines
Sun 11/92:49 pmLIH - ORD
1 stop11h 08mAmerican Airlines
Deal found 9/16$423
This Alaska Airlines deal was found by Cheapflights users on 9/18. 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 11/278:20 amORD - LIH
2 stops16h 10mAlaska Airlines
Fri 12/52:53 pmLIH - ORD
1 stop19h 16mAlaska Airlines
Deal found 9/18$429
This Alaska Airlines deal was found by Cheapflights users on 9/17. 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 12/39:15 amORD - ITO
2 stops15h 15mAlaska Airlines
Thu 12/1112:05 pmITO - ORD
2 stops14h 16mAlaska Airlines
Deal found 9/17$435
This Delta deal was found by Cheapflights users on 9/16. 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.
Sun 11/27:37 amORD - LIH
1 stop16h 28mDelta
Sun 11/99:29 pmLIH - ORD
2 stops17h 16mDelta
Deal found 9/16$436
This Alaska Airlines deal was found by Cheapflights users on 9/18. 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 12/33:05 pmORD - LIH
2 stops26h 44mAlaska Airlines
Sun 12/142:53 pmLIH - ORD
1 stop19h 16mAlaska Airlines
Deal found 9/18$438

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Hawaii 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 September 19, 2025.
Use the filters below to find and compare flights from Chicago to Hawaii that are best for you.

Fly from

Chicago

Fly to

Hawaii

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/8

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

Wed 10/22

9:30 pm-1:30 pm

1 stop11h 00m

$387

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/22

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

Mon 10/27

9:30 pm-4:50 pm

2 stops14h 20m

$392

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/29

6:08 am-5:30 pm

2 stops16h 22m

Kona Intl

Tue 11/4

9:30 pm-6:49 pm

2 stops17h 19m

$392

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 12/4

3:05 pm-1:53 pm

1 stop26h 48m

Lihue

Thu 12/11

2:53 pm-6:54 pm

1 stop24h 01m

$399

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 11/3

7:37 am-8:05 pm

1 stop16h 28m

Lihue

Mon 11/10

9:29 pm-5:18 pm

1 stop15h 49m

$410

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

6:08 am-5:30 pm

2 stops16h 22m

Kona Intl

Fri 10/31

9:30 pm-4:50 pm

2 stops14h 20m

$420

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 12/4

7:59 pm-1:53 pm

1 stop21h 54m

Lihue

Tue 12/9

2:53 pm-6:54 pm

1 stop24h 01m

$421

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Mon 11/17

7:10 am-4:58 pm

1 stop13h 48m

Lihue

Mon 11/24

2:31 pm-5:00 am

1 stop10h 29m

$423

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/21

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-5:18 pm

1 stop14h 38m

$423

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 10/22

7:37 am-7:05 pm

1 stop16h 28m

Lihue

Fri 10/31

9:40 pm-5:18 pm

1 stop14h 38m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii 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 Hawaii

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $469). Flying from Chicago to Hawaii 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 HI?

Find hourly flight availability from Chicago to Hawaii. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 19, 2025.

When flying from Chicago to Hawaii, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Hawaii

Explore weekly flight availability from Chicago to Hawaii. 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 September 19, 2025.

The most flights from CHI to USHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, 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 Hawaii?

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated September 19, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Chicago to Hawaii have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
8.0
Very good

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Chicago to Hawaii Travel Guide

When you're looking for a tropical escape from the hustle and bustle of the Windy City, Hawaii makes a great choice. With their perfect weather and laid-back lifestyle, the Hawaiian Islands can help you relax and recharge. Whether you want to kick back with a book on Hulopoe Beach or hike through the jungle on the Manoa Falls Trail, the friendly locals and well-developed infrastructure make your journey a breeze. A direct flight between Chicago and Hawaii reduces travel time, so you can reach the islands quickly.

Hawaii is the perfect island vacation spot for travelers from Chicago: it's accessible by a direct flight, and it requires no passport or customs. Once you arrive on Oahu or Maui, you'll be greeted with balmy breezes and smiling locals. If you're longing for sunshine and sunbathing, head for the islands' many stunning beaches. On Maui, try Kaanapali Beach or Wailea Beach, and on the Big Island, check out the unusual Punaluu Black Sand Beach. If you're visiting Honolulu, the famous Waikiki Beach is a must-see. When you're ready to get out into the wild, check out the lava flows at Hawaii Volcanoes National Park or hike through the otherworldly landscapes of Haleakala National Park. Cool off in Hanakapiai Falls, or marvel at the steep cliffs of the Na Pali Coast.

If you're dreaming of a vacation to sunny Hawaii, start planning today. Use the Cheapflights search engine to browse a wide variety of fares on nonstop flights between Chicago and Honolulu or Kahului.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Hawaii. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Chicago to Hawaii?

    When you're traveling from Chicago, it's possible to fly direct to two different cities in Hawaii. The flight to Honolulu lasts approximately nine hours from gate to gate, and the flight to Kahului takes slightly longer than nine hours.

  • Which airlines operate flights from Chicago to Hawaii?

    United Airlines is the only carrier that flies direct between Chicago and the state of Hawaii. United flies to the island of Oahu and the island of Maui.

  • How frequent are flights between Chicago and Hawaii?

    There is one flight per day from Chicago to Honolulu, and one daily flight to the city of Kahului. Both flights leave from O'Hare International Airport.

  • Which airports serve Chicago to Hawaii?

    Direct flights from Chicago to Hawaii leave from the O'Hare International Airport. If you're visiting Honolulu, you'll land at the Honolulu International Airport, and if you are traveling to Kahului, expect to land at the Kahului Airport. All three airports provide a variety of ground transportation options.

  • Which direct flight route between Chicago and Hawaii is cheapest?

    You can get the best fares when traveling between Chicago and Honolulu, with flights to Kahului close behind. Prices drop dramatically when you book your departing and returning flights together on a round-trip ticket.

  • How busy are the airports in Chicago and Hawaii?

    Flying to Hawaii from Chicago means you will start your journey at O'Hare International Airport (ORD) on the northwest side of the city. O’Hare is in the top 10 busiest airports in the world and is a major hub for airlines like United and American Airlines. In Hawaii, the three largest international airports are Hilo International Airport (ITO) which serves as the destination airport for most of east Hawaii. The next is Daniel K. Inouye International Airport, also known as Honolulu International Airport (HNL), and is also located on the northwest side of the city center. Honolulu International Airport is the largest airport serving Hawaii and the major hub for Hawaiian Airlines. Lastly, is Ellison Onizuka Kona International Airport (KOA) or Kona International Airport. This airport serves the west side of Hawaii.

  • Which airlines fly directly from Chicago to Hawaii?

    Unfortunately, direct flights from Chicago to Hawaii are not currently available, but there are plenty of flight options to choose from. If you fly from Chicago to Hilo International Airport, you will most likely have one stopover. Most flights are operated by United Airlines on this common flight route. From Chicago to Honolulu, the major airline most commonly operating this route is Delta Airlines. Finally, if you’re headed to the west area of Hawaii, you’ll most likely fly into Kona International Airport. The main airline operating this flight path is American Airlines. All these airlines have differing hub cities, which means the stopover city will be unique to the airline that is operating the flight.

  • What are the stopover options between Chicago to Hawaii?

    Flights from Chicago to Hawaii include at least one stopover, and that stopover city depends on what airlines you’re flying with and which destination you land at in Hawaii. From Hilo International from Chicago, you will most likely have a stopover in Los Angeles (LAX) before heading to your final destination. If you’re flying into Honolulu International Airport (HNL) with Delta Airlines, there are a few common stopover cities including Seattle, Salt Lake City, and Atlanta. Flights with American Airlines from Chicago to Kona International Airport have stopovers in cities including Phoenix and Dallas.

  • Do I need a passport or visa to fly from Chicago to Hawaii?

    No, you will not need a passport or visa as an American citizen heading from Chicago to Hawaii. You will however need a valid driver’s license from the state you live in. If you don’t have a driver’s license you will need a valid identification card from your home state. Both your driver’s license or identification card will need to be valid for the length of your travel, otherwise, you will need to renew either before heading on your journey.

  • What alternative but sustainable transport option can I use to travel from Chicago to Hawaii?

    Hawaii is situated about 4194 mi from Chicago. Therefore, flights offer the most sustainable mode that passengers can use to travel from their origin to their destination. This is so because flights offer direct transport services to many passengers in one trip. Unfortunately, there are no other sustainable modes of getting from Chicago to Hawaii because of the Pacific Ocean crossing. Therefore, flights are the only sustainable way to get you to Hawaii from Chicago.

  • What can I do to reduce my carbon footprint when flying from Chicago to Hawaii?

    If you are a passenger looking to travel sustainably from Chicago to Hawaii, consider settling for a direct flight. The route is serviced by several direct flights as well as others with one or two stopovers. Direct flights utilize less fuel for the journey than those with one or more stopovers. This is so because flights involving several stopovers do not use the shortest route and consume more fuel when landing and taking off from multiple destinations. Therefore, fly directly from the origin to the destination to reduce your carbon footprint.

  • What information is necessary for identifying a sustainable airline for my trip from Chicago to Hawaii?

    If you need to identify a sustainable airline for flying from Chicago to Hawaii, think about looking for the SAF certification. SAF-certified airlines have engines that are designed to use fossil-based fuel rather than conventional petroleum-based fuel. Fossil fuel is more sustainable because its production does not emit carbon gases into the atmosphere as opposed to petroleum-based fuel. Therefore, flying in a SAF-certified airline is a great way to promote the sustainability of the environment.

  • How long is the flight from Chicago to Hawaii?

    Airlines like Delta, Alaska Airlines, and United Airlines fly from Chicago to Hawaii in about 13h 48m. The time it takes to get you to your destination can typically vary by up to 13h. The distance from Chicago to Hawaii is about 4280 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $181. Delta flights start at $205 while deals on United Airlines start at $212 one-way.

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

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

    The top 3 most reliable airlines when flying from Chicago to Hawaii are United Airlines (63%), Air New Zealand (63%) and Qantas Airways (0%).

  • What are the cheapest flights from Chicago to Hawaii?

    Looking at all options, your cheapest flight can be booked for $326. While the most popular route (Chicago O'Hare Intl - Honolulu) can be booked for $466 on average, our data indicates $2,166 when flying from Chicago to Hawaii.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $469). Flying from Chicago to Hawaii 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

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Alternative routes for Chicago to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chicago to Hawaii

Discover the top 6 airlines that operate flights from Chicago to Hawaii. 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$231Average$638FlexibilityNo cancel feeOn-time85%
DeltaCheapest$330Average$588FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$379Average$707FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$420Average$707FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$424Average$779FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$441Average$937FlexibilityNo cancel feeOn-time69%

Helpful tips for your next trip to Hawaii

Get useful tips and recommendations to enhance your travel experience on your next trip to Hawaii. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
  • American Airlines is one of the airlines that gets passengers from Chicago to Hawaii. It does so sustainably by ensuring it has fuel-efficient planes in its fleet servicing the route.
  • Chicago is committed to promoting environmental sustainability. As a result, the city requires the airports operating in the region to monitor their carbon emissions to ensure they are within acceptable standards.
  • The O’Hare International Airport (ORD) will be your departure airport if you are traveling from Chicago to Hawaii. The airport is known to have an elaborate waste collection mechanism that sorts plastics and other non-biodegradable materials ready for reuse or recycling.

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