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$70+ Cheap flights from Washington, D.C. (WAS) 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 87 days in advance, depart on a Friday or Wednesday and return on a Thursday

Cheap flight deals from Washington, D.C. to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) 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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$95
(Mytrip)

One-way from

$70
(Southwest)

Popular in

March

Cheapest in

September

Average price

$244

Good round-trip deal

$135 or less

Good one-way deal

$72 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
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From Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).
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Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
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Find flight deals from Washington, D.C. to Chicago

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/145:47 pmBWI - ORD
1 stop5h 41mSpirit Airlines
sáb. 5/176:00 amORD - BWI
1 stop9h 51mSpirit Airlines
Deal found 2/20$93
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/56:00 amBWI - ORD
1 stop11h 31mFrontier
mar. 3/115:43 pmORD - BWI
1 stop5h 34mFrontier
Deal found 2/19$100
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/284:11 pmBWI - MDW
Nonstop2h 12mFrontier
mié. 4/21:05 pmMDW - BWI
Nonstop1h 50mFrontier
Deal found 2/18$105
This Priceline deal was found by Cheapflights users on 2/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/25:47 pmBWI - ORD
1 stop5h 41mMultiple Airlines
sáb. 6/76:01 pmORD - BWI
1 stop5h 34mMultiple Airlines
Deal found 2/19$117
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.
mar. 3/256:45 amBWI - MDW
Nonstop2h 10mSouthwest
mié. 3/266:35 pmMDW - BWI
Nonstop1h 45mSouthwest
Deal found 2/17$139
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/56:03 pmIAD - ORD
1 stop25h 51mFrontier
mié. 3/268:43 amORD - IAD
1 stop11h 23mFrontier
Deal found 2/19$157
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/91:03 pmDCA - ORD
1 stop12h 20mFrontier
mar. 3/116:45 amORD - DCA
1 stop9h 14mFrontier
Deal found 2/19$160
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/125:54 pmIAD - MDW
1 stop26h 41mFrontier
lun. 3/172:51 pmMDW - IAD
1 stop21h 25mFrontier
Deal found 2/19$160
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/91:03 pmDCA - MDW
1 stop12h 16mFrontier
mar. 3/116:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 2/19$160
This United Airlines deal was found by Cheapflights users on 2/19. 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.
mar. 4/11:00 pmDCA - ORD
Nonstop2h 15mUnited Airlines
mar. 4/82:00 pmORD - DCA
Nonstop2h 00mUnited Airlines
Deal found 2/19$177
This Southwest deal was found by Cheapflights users on 2/19. 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. 3/56:55 amDCA - MDW
Nonstop2h 15mSouthwest
mié. 3/127:35 amMDW - DCA
Nonstop1h 45mSouthwest
Deal found 2/19$177
This United Airlines deal was found by Cheapflights users on 2/19. 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.
jue. 3/136:10 amIAD - ORD
Nonstop2h 15mUnited Airlines
mar. 3/186:18 pmORD - IAD
Nonstop1h 55mUnited Airlines
Deal found 2/19$178

Find flights from Washington, D.C. to Chicago within your budget

Customize your flight search to find flights from Washington, D.C. 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 febrero 20, 2025.

Fly from

Washington, D.C.

Fly to

Chicago

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

mié. 5/14

5:47 pm-10:28 pm

1 stop5h 41m

Chicago O'Hare Intl

sáb. 5/17

6:00 am-4:51 pm

1 stop9h 51m

$93

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

mié. 3/5

6:00 am-4:31 pm

1 stop11h 31m

Chicago O'Hare Intl

mar. 3/11

5:43 pm-12:17 am

1 stop5h 34m

$100

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

vie. 3/28

4:11 pm-5:23 pm

Nonstop2h 12m

Chicago Midway

mié. 4/2

1:05 pm-3:55 pm

Nonstop1h 50m

$105

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

lun. 6/2

5:47 pm-10:28 pm

1 stop5h 41m

Chicago O'Hare Intl

sáb. 6/7

6:01 pm-12:35 am

1 stop5h 34m

$117

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

mar. 3/25

6:45 am-7:55 am

Nonstop2h 10m

Chicago Midway

mié. 3/26

6:35 pm-9:20 pm

Nonstop1h 45m

$139

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

mié. 3/5

6:03 pm-6:54 pm

1 stop25h 51m

Chicago O'Hare Intl

mié. 3/26

8:43 am-9:06 pm

1 stop11h 23m

$157

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

dom. 3/9

1:03 pm-12:23 am

1 stop12h 20m

Chicago O'Hare Intl

mar. 3/11

6:45 am-4:59 pm

1 stop9h 14m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mié. 3/12

5:54 pm-7:35 pm

1 stop26h 41m

Chicago Midway

lun. 3/17

2:51 pm-1:16 pm

1 stop21h 25m

$160

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

dom. 3/9

1:03 pm-12:19 am

1 stop12h 16m

Chicago Midway

mar. 3/11

6:40 am-4:59 pm

1 stop9h 19m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mar. 4/1

1:00 pm-2:15 pm

Nonstop2h 15m

Chicago O'Hare Intl

mar. 4/8

2:00 pm-5:00 pm

Nonstop2h 00m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 58 results
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Compare providers for flights from Washington, D.C. 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 Washington, D.C. to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Washington, D.C.-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C.-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 Washington, D.C.-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 Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. 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.

Travel insights for flights from Washington, D.C. to Chicago

Get recent, data-driven insights about flights from Washington, D.C. to Chicago including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Washington, D.C. to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Washington, D.C. to Chicago. Price data was last updated on February 14, 2025.

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 87 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 Washington, D.C. to Chicago?

Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from WAS to CHI?

Find hourly flight availability from Washington, D.C. 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 febrero 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Washington, D.C. to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Chicago. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Washington, D.C. to Chicago

Explore weekly flight availability from Washington, D.C. 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 febrero 20, 2025.

The most flights from WAS to CHI are scheduled on a Thursday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 febrero 20, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,412 reviews
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,691 reviews
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,227 reviews
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,071 reviews
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,771 reviews
Southwest
8.1
Very good
4,412 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Washington, D.C. to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

    Cheapflights users have booked flights from Washington, D.C. to Chicago round-trip from $95. Other airlines that can offer you cheap pricing are Frontier, from $100, and Southwest, from $139. Spirit Airlines is 62% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

    One-way options have recently been found by users for as low as $70 on Southwest. Other airlines that offer cheap prices include Frontier from $71 and Spirit Airlines from $73 one-way.

  • What are the most popular routes from Washington, D.C. to Chicago?

    The most popular route from Washington, D.C. to Chicago is Washington, D.C. Dulles Intl - Chicago O'Hare Intl. You may also consider Baltimore/Washington - Chicago O'Hare Intl or Washington, D.C. Reagan-National - Chicago O'Hare Intl.

  • What are the most reliable airlines from Washington, D.C. to Chicago?

    The top 3 most reliable airlines when flying from Washington, D.C. to Chicago are Ethiopian Air (85%), Copa Airlines (83%) and ANA (83%).

  • What are the cheapest flights from Washington, D.C. to Chicago?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) can be booked for $122 on average our data indicates $1,024 when flying from Washington, D.C. to Chicago.

  • Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

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

  • How can I find direct flights from Washington, D.C. to Chicago?

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

  • Can I find deals for business class flights from Washington, D.C. to Chicago?

    Yes. Cheapflights offers flight deals from Washington, D.C. 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 Washington, D.C. to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Washington, D.C.?

Book flights to Washington, D.C. if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Washington, D.C. to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
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Reagan-National to Paducah flights

Top 6 airlines flying from Washington, D.C. to Chicago

Discover the top 6 airlines that operate flights from Washington, D.C. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$173FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$197FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$133Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$158Average$292FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$294FlexibilityNo cancel feeOn-timeN/A
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