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Windhoek

$1,498+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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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 septiembre 11, 2025.

Round-trip from

$1,484
(oojo)
From Chicago (CHI) to Windhoek
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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 septiembre 11, 2025.

This oojo deal was found by Cheapflights users on 9/9. 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.
jue. 11/131:00 pmORD - WDH
2 stops40h 20mEthiopian Air
dom. 11/302:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 9/9$1,498
This Ovago deal was found by Cheapflights users on 9/11. 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.
jue. 11/139:50 pmORD - WDH
1 stop25h 55mLufthansa
dom. 11/307:55 pmWDH - ORD
1 stop25h 15mLufthansa
Deal found 9/11$1,627
This Gurufare deal was found by Cheapflights users on 9/9. 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.
jue. 11/139:50 pmORD - WDH
1 stop25h 55mMultiple Airlines
dom. 11/308:00 pmWDH - ORD
2 stops28h 20mMultiple Airlines
Deal found 9/9$1,651
This Gurufare deal was found by Cheapflights users on 9/9. 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.
mar. 12/234:10 pmORD - WDH
2 stops41h 05mSWISS
sáb. 1/108:40 pmWDH - ORD
2 stops27h 40mSWISS
Deal found 9/9$1,680
This Gurufare deal was found by Cheapflights users on 9/9. 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.
mar. 12/234:10 pmORD - WDH
2 stops41h 05mMultiple Airlines
vie. 1/98:00 pmWDH - ORD
2 stops26h 00mMultiple Airlines
Deal found 9/9$1,695
This United Airlines deal was found by Cheapflights users on 9/10. 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. 10/74:00 pmORD - WDH
2 stops37h 50mUnited Airlines
mar. 10/141:40 pmWDH - ORD
2 stops26h 56mUnited Airlines
Deal found 9/10$1,698
This Ethiopian Air deal was found by Cheapflights users on 9/10. 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 Ethiopian Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/31:05 pmORD - WDH
2 stops40h 15mEthiopian Air
dom. 12/72:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 9/10$1,722
This Ovago deal was found by Cheapflights users on 9/9. 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.
mié. 12/244:10 pmORD - WDH
2 stops37h 25mSWISS
jue. 1/82:30 pmWDH - ORD
2 stops33h 50mSWISS
Deal found 9/9$1,730

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 septiembre 11, 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

jue. 11/13

1:00 pm-1:20 pm

2 stops40h 20m

Windhoek Hosea Kutako Intl

dom. 11/30

2:30 pm-7:40 am

2 stops25h 10m

$1,498

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jue. 2/5

9:00 am-1:20 pm

3 stops44h 20m

Windhoek Hosea Kutako Intl

mié. 2/11

2:30 pm-7:40 am

2 stops25h 10m

$1,553

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jue. 11/13

9:50 pm-7:45 am

1 stop25h 55m

Windhoek Hosea Kutako Intl

dom. 11/30

7:55 pm-1:10 pm

1 stop25h 15m

$1,627

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

mar. 1/13

8:20 pm-1:20 pm

2 stops33h 00m

Windhoek Hosea Kutako Intl

dom. 1/18

2:30 pm-10:05 am

2 stops27h 35m

$1,648

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

jue. 11/13

9:50 pm-7:45 am

1 stop25h 55m

Windhoek Hosea Kutako Intl

dom. 11/30

8:00 pm-4:20 pm

2 stops28h 20m

$1,651

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

mié. 2/4

4:20 pm-9:15 am

1 stop32h 55m

Windhoek Hosea Kutako Intl

mar. 2/10

8:00 pm-3:20 pm

1 stop27h 20m

$1,654

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

dom. 1/4

10:35 pm-9:35 am

1 stop27h 00m

Windhoek Hosea Kutako Intl

dom. 1/11

8:00 pm-1:10 pm

1 stop25h 10m

$1,655

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 septiembre 11, 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 31% versus a flight at noon.

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 40h 20m. 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.

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

    Currently, March is the cheapest month in which you can book a flight from Chicago to Windhoek (average of $1,465). Flying from Chicago to Windhoek in July is currently the most expensive (average of $1,917). 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

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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Ethiopian AirCheapest$1,229Average$1,572FlexibilityNo cancel feeOn-time72%

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