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Windhoek

$1,308+ Cheap flights from Chicago (CHI) to Windhoek

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
Dec 23 — Dec 301
Tue 12/23
Tue 12/30
1 adult, Economy
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Find 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 November 23, 2025.

This oojo deal was found by Cheapflights users on 11/22. 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.
Mon 12/87:00 amORD - WDH
3 stops46h 20mEthiopian Air
Thu 12/182:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 11/22$1,544
This Expedia deal was found by Cheapflights users on 11/22. 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.
Mon 12/229:40 pmORD - WDH
2 stops50h 05mLufthansa
Sun 1/188:00 pmWDH - ORD
1 stop23h 10mLufthansa
Deal found 11/22$1,695
This Expedia deal was found by Cheapflights users on 11/22. 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.
Mon 12/229:40 pmORD - WDH
2 stops50h 05mMultiple Airlines
Sun 1/182:30 pmWDH - ORD
2 stops33h 50mMultiple Airlines
Deal found 11/22$1,712
This Gurufare deal was found by Cheapflights users on 11/22. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/84:20 pmORD - WDH
2 stops32h 55mMultiple Airlines
Thu 12/188:40 pmWDH - ORD
1 stop29h 45mMultiple Airlines
Deal found 11/22$1,867
This Ovago deal was found by Cheapflights users on 11/22. 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.
Mon 12/84:20 pmORD - WDH
1 stop32h 55mLufthansa
Thu 12/188:40 pmWDH - ORD
1 stop29h 45mLufthansa
Deal found 11/22$1,900

Cheap 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 November 23, 2025.

Round-trip from

$1,308
(oojo)
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 November 23, 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

Thu 3/26

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

Sun 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,308

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Thu 3/26

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

Sun 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,439

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Mon 12/8

7:00 am-1:20 pm

3 stops46h 20m

Windhoek Hosea Kutako Intl

Thu 12/18

2:30 pm-7:40 am

2 stops25h 10m

$1,544

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 5/2

10:15 am-5:40 pm

2 stops24h 25m

Windhoek Hosea Kutako Intl

Sat 5/9

2:30 pm-8:15 am

2 stops24h 45m

$1,564

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 1/30

8:45 am-1:20 pm

3 stops44h 35m

Windhoek Hosea Kutako Intl

Sun 2/15

2:30 pm-7:40 am

2 stops25h 10m

$1,585

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Thu 3/26

10:50 pm-7:45 am

1 stop25h 55m

Windhoek Hosea Kutako Intl

Sun 4/5

7:15 pm-2:50 pm

1 stop26h 35m

$1,588

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 5/2

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

Sat 5/9

2:30 pm-8:15 am

2 stops24h 45m

$1,599

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Tue 2/3

6:00 pm-7:45 am

1 stop29h 45m

Windhoek Hosea Kutako Intl

Tue 2/17

8:00 pm-1:30 pm

2 stops25h 30m

$1,604

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 1/30

6:35 pm-9:35 am

2 stops31h 00m

Windhoek Hosea Kutako Intl

Sun 2/15

8:00 pm-12:10 pm

2 stops24h 10m

$1,634

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sun 2/1

4:10 pm-1:35 pm

2 stops37h 25m

Windhoek Hosea Kutako Intl

Mon 2/16

2:30 pm-4:20 pm

2 stops33h 50m

$1,654

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November 23, 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 November 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Ethiopian AirCheapest$1,248Average$1,597FlexibilityNo cancel feeOn-time72%

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