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$95+ Cheap flights from Oklahoma City (OKC) 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Find cheap flights from Oklahoma City 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 Oklahoma City Will Rogers World to Chicago are usually found in April or February, booked 77 days in advance, depart on a Thursday or Saturday and return on a Saturday

Cheap flight deals from Oklahoma City to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oklahoma City (OKC) 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$279
(Southwest)

One-way from

$95
(Frontier)

Popular in

March

Cheapest in

April

Average price

$338

Good round-trip deal

$344 or less

Good one-way deal

$179 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
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From Oklahoma City Will Rogers World to Chicago (CHI)
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One-way flight from Oklahoma City Will Rogers World to Chicago (CHI)
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago (CHI).
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Find flight deals from Oklahoma City to Chicago

Cheapest flights from Oklahoma City to Chicago
Explore the most affordable flight options available from Oklahoma City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/167:00 amOKC - MDW
Nonstop1h 55mSouthwest
Wed 8/2012:45 pmMDW - OKC
1 stop9h 05mSouthwest
Deal found 4/30$279
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 7/2910:27 amOKC - ORD
Nonstop2h 13mAmerican Airlines
Sat 8/25:00 amORD - OKC
1 stop4h 34mAmerican Airlines
Deal found 4/30$279
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/218:05 pmOKC - ORD
1 stop27h 47mFrontier
Sun 5/256:00 amORD - OKC
1 stop13h 37mFrontier
Deal found 4/29$280
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:24 pmOKC - MDW
1 stop10h 54mFrontier
Sun 7/69:12 pmMDW - OKC
1 stop10h 45mFrontier
Deal found 4/30$282
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/305:55 pmOKC - ORD
Nonstop2h 20mUnited Airlines
Mon 6/29:15 amORD - OKC
Nonstop2h 39mUnited Airlines
Deal found 4/29$285
This Delta deal was found by Cheapflights users on 5/1. 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 7/97:00 amOKC - MDW
1 stop4h 53mDelta
Sat 7/121:46 pmMDW - OKC
1 stop6h 35mDelta
Deal found 5/1$289
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1612:55 pmOKC - ORD
2 stops9h 05mSouthwest
Wed 8/201:50 pmORD - OKC
2 stops8h 20mSouthwest
Deal found 4/30$299
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 6/145:30 amOKC - ORD
1 stop7h 00mDelta
Sat 6/213:58 pmORD - OKC
1 stop4h 25mDelta
Deal found 4/29$303
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/102:50 pmOKC - ORD
1 stop22h 14mAlaska Airlines
Mon 10/139:00 pmORD - OKC
1 stop16h 54mAlaska Airlines
Deal found 4/29$526

Cheapflights Fare Finder

Customize your flight search to find flights from Oklahoma City 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 May 1, 2025.
Use the filters below to find and compare flights from Oklahoma City to Chicago that are best for you.

Fly from

Oklahoma City

Fly to

Chicago

Route

Depart

Return

Price

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 8/16

7:00 am-8:55 am

Nonstop1h 55m

Chicago Midway

Wed 8/20

12:45 pm-9:50 pm

1 stop9h 05m

$279

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 7/29

10:27 am-12:40 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sat 8/2

5:00 am-9:34 am

1 stop4h 34m

$279

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Wed 5/21

8:05 pm-11:52 pm

1 stop27h 47m

Chicago O'Hare Intl

Sun 5/25

6:00 am-7:37 pm

1 stop13h 37m

$280

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 7/3

12:24 pm-11:18 pm

1 stop10h 54m

Chicago Midway

Sun 7/6

9:12 pm-7:57 am

1 stop10h 45m

$282

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 5/30

5:55 pm-8:15 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 6/2

9:15 am-11:54 am

Nonstop2h 39m

$285

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 5/30

1:47 pm-9:27 pm

1 stop7h 40m

Chicago Midway

Sat 5/31

1:55 pm-8:34 pm

1 stop6h 39m

$303

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 6/14

5:30 am-12:30 pm

1 stop7h 00m

Chicago O'Hare Intl

Sat 6/21

3:58 pm-8:23 pm

1 stop4h 25m

$303

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 5/27

11:15 am-4:45 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 6/3

7:30 am-4:10 pm

2 stops8h 40m

$318

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Thu 5/29

3:23 pm-12:17 am

1 stop8h 54m

$95

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 6/3

3:24 pm-10:44 pm

1 stop7h 20m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 18 results
1
2

Compare providers for flights from Oklahoma City 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 Oklahoma City to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust 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 Oklahoma City-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Oklahoma City-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Oklahoma City-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oklahoma City-Chicago flights, Cheapflights users trust Mytrip the most. Mytrip 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 Oklahoma City-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Oklahoma City to Chicago 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 Oklahoma City to Chicago trip
Airlines
Japan Airlines

JAL's economy seats offer 34 inches of legroom and seat-back screens on international flights.


JAL's Wi-Fi is available on international flights, but streaming is not supported.

Read more about Japan Airlinesby Emily Zemler
United Airlines

United's Economy Plus offers extra legroom and priority boarding for MileagePlus Premier members.


Prepay for checked bags on United to save fees 24 hours before your flight.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.


Southwest's Early Bird check-in provides priority boarding 36 hours before departure.

Read more about Southwestby Marisa Garcia
Our travel experts
Emily Zemler

Emily Zemler

Expert on Japan Airlines

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more

Best time to book a flight from Oklahoma City to Chicago

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

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

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

To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 77 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 Oklahoma City to Chicago?

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

Find hourly flight availability from Oklahoma City 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 May 1, 2025.

One of the essential ways to save on airfare from Oklahoma City to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 47% on airfare.

What is the cheapest day to fly from Oklahoma City to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oklahoma City to Chicago. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Oklahoma City to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Oklahoma City to Chicago

Explore weekly flight availability from Oklahoma City 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 May 1, 2025.

The most flights from OKC to CHI are scheduled on a Wednesday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 May 1, 2025.
Read through reviews of airlines operating flights from Oklahoma City to Chicago, such as Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Oklahoma City 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 Oklahoma City to Chicago?

    Oklahoma City Will Rogers World (OKC) is the airport you will fly out of if you book a flight from Oklahoma City to Chicago. You should not have trouble finding flights to Chicago from Will Rogers World; the airport handles an average of 15 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Oklahoma City airport to Chicago. It is only a 7.0 mi journey to Will Rogers World (OKC) from Oklahoma City’s city center.

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

    Cheapflights users have booked flights from Oklahoma City to Chicago round-trip from $279. Other airlines that can offer you cheap pricing are American Airlines, from $279, and Frontier, from $280. Users have found that Southwest is 20% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $95. Allegiant Air flights start at $117 while deals on Southwest start at $128 one-way.

  • What are the most reliable airlines from Oklahoma City to Chicago?

    Before booking your flight to Chicago from Oklahoma City, check out the most reliable airlines to get you to your destination on time: Japan Airlines (89%), Emirates (85%), Republic Airways( 85%).

  • What are the cheapest flights from Oklahoma City to Chicago?

    Looking for the cheapest flight from Oklahoma City to Chicago? While on average our users pay $1,000, our data indicates the cheapest price to be $161. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $255.

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

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

  • How can I find direct flights from Oklahoma City to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Oklahoma City 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 Oklahoma City to Chicago?

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

Book flights to Oklahoma City if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Oklahoma City to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oklahoma City to Chicago

Discover the top 4 airlines that operate flights from Oklahoma City 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$123Average$178FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$233Average$355FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$253Average$421FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$300Average$363FlexibilityNo cancel feeOn-time63%

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