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Windhoek

$1,043+ Cheap flights from Chicago (CHI) to Windhoek

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
janv. 3 — janv. 101
sam. 1/3
sam. 1/10
1 adult, Economy
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Cheap flight deals from Chicago to Windhoek

Cheapest flights from Chicago to Windhoek
Explore the most affordable flight options available from Chicago to Windhoek. Find the lowest fares from popular airlines and budget airlines, with prices last updated on décembre 4, 2025.

This oojo deal was found by Cheapflights users on 12/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/81:05 pmORD - WDH
3 stops40h 15mEthiopian Air
mar. 12/232:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 12/2$1,584
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/81:05 pmORD - WDH
2 stops40h 15mMultiple Airlines
mar. 12/238:00 pmWDH - ORD
1 stop27h 20mMultiple Airlines
Deal found 12/2$2,019
This Mytrip deal was found by Cheapflights users on 12/2. 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.
sam. 12/66:50 pmORD - WDH
3 stops34h 30mMultiple Airlines
lun. 12/88:40 pmWDH - ORD
2 stops27h 40mMultiple Airlines
Deal found 12/2$2,133
This Ovago deal was found by Cheapflights users on 12/2. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/66:00 pmORD - WDH
1 stop29h 45mLufthansa
lun. 12/88:40 pmWDH - ORD
1 stop29h 45mLufthansa
Deal found 12/2$2,197
This Ovago deal was found by Cheapflights users on 12/2. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:25 pmORD - WDH
1 stop30h 50mLufthansa
mar. 12/238:00 pmWDH - ORD
1 stop32h 05mLufthansa
Deal found 12/2$2,204

Find flight deals from Chicago to Windhoek

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Windhoek (NA1). 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 décembre 4, 2025.

Round-trip from

$1,309
(oojo)

One-way from

$1,043
(Ethiopian Air)
From Chicago (CHI) to Windhoek
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One-way flight from Chicago (CHI) to Windhoek
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Windhoek 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 décembre 4, 2025.
Use the filters below to find and compare flights from Chicago to Windhoek that are best for you.

Fly from

Chicago

Fly to

Windhoek

Route

Depart

Return

Price

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jeu. 3/26

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

dim. 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,309

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

mar. 3/3

11:50 am-1:20 pm

2 stops41h 30m

Windhoek Hosea Kutako Intl

jeu. 3/26

2:30 pm-11:05 am

2 stops27h 35m

$1,443

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jeu. 5/21

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

lun. 6/1

2:30 pm-8:15 am

2 stops24h 45m

$1,522

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

ven. 5/22

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

lun. 6/1

2:30 pm-8:15 am

2 stops24h 45m

$1,556

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

sam. 5/23

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

mar. 6/2

2:30 pm-8:15 am

2 stops24h 45m

$1,567

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jeu. 5/21

10:15 am-5:40 pm

2 stops24h 25m

Windhoek Hosea Kutako Intl

lun. 6/1

2:30 pm-8:15 am

2 stops24h 45m

$1,585

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jeu. 3/26

10:50 pm-7:45 am

1 stop25h 55m

Windhoek Hosea Kutako Intl

dim. 4/5

7:15 pm-2:50 pm

1 stop26h 35m

$1,589

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jeu. 3/26

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

dim. 4/5

2:30 pm-2:22 pm

3 stops30h 52m

$1,596

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

ven. 5/22

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

lun. 6/1

2:30 pm-8:15 am

2 stops24h 45m

$1,630

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

sam. 5/23

10:15 am-1:20 pm

1 stop20h 05m

$1,043

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 12 results
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Best time to book a flight from Chicago to Windhoek

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

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

Find hourly flight availability from Chicago to Windhoek. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated décembre 4, 2025.

When flying from Chicago to Windhoek, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 38% versus a flight in the evening.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Windhoek. 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 Windhoek?

    Ethiopian Air can get you from Chicago to Windhoek in just under 20h 05m. Your travel time can differ by up to . The distance between Chicago and Windhoek is about 8007 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Windhoek by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Windhoek

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Hosea Kutako Intl flights
St. Louis to Hosea Kutako Intl flights

Top airline flying from Chicago to Windhoek

Discover the top airline that operate flights from Chicago to Windhoek. 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 décembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Ethiopian AirCheapest$1,248Average$1,597FlexibilityNo cancel feeOn-time72%

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