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Windhoek

$1,243+ 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
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Chicago to Windhoek

Best flights from Chicago to Windhoek
Discover carefully curated flight deals from Chicago to Windhoek that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 26, 2025.

This oojo deal was found by Cheapflights users on 12/23. 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.
Thu 3/2610:15 amORD - WDH
1 stop20h 05mEthiopian Air
Sun 4/52:30 pmWDH - ORD
2 stops24h 45mEthiopian Air
Deal found 12/23$1,243
This Gurufare deal was found by Cheapflights users on 12/24. 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.
Thu 3/2610:15 amORD - WDH
2 stops24h 25mMultiple Airlines
Sun 4/52:30 pmWDH - ORD
2 stops24h 45mMultiple Airlines
Deal found 12/24$1,307
This Etihad Airways deal was found by Cheapflights users on 12/23. 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 Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:10 pmORD - WDH
2 stops40h 10mEtihad Airways
Sun 3/152:30 pmWDH - ORD
2 stops49h 05mEtihad Airways
Deal found 12/23$1,572
This Ethiopian Air deal was found by Cheapflights users on 12/23. 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.
Wed 3/1110:15 amORD - WDH
1 stop20h 05mEthiopian Air
Sun 3/152:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 12/23$1,327
This Gurufare deal was found by Cheapflights users on 12/24. 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.
Fri 3/2710:15 amORD - WDH
2 stops26h 30mMultiple Airlines
Sun 4/52:30 pmWDH - ORD
2 stops24h 45mMultiple Airlines
Deal found 12/24$1,397
This oojo deal was found by Cheapflights users on 12/25. 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.
Thu 4/2310:15 amORD - WDH
1 stop20h 05mEthiopian Air
Thu 5/72:30 pmWDH - ORD
2 stops24h 45mEthiopian Air
Deal found 12/25$1,375
This oojo deal was found by Cheapflights users on 12/24. 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.
Sat 1/241:00 pmORD - WDH
2 stops40h 20mEthiopian Air
Sun 2/82:30 pmWDH - ORD
2 stops25h 10mEthiopian Air
Deal found 12/24$1,566

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 December 26, 2025.

Round-trip from

$1,243
(oojo)
From Chicago (CHI) to Windhoek
Search Deals

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 December 26, 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

$1,243

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Thu 3/26

10:15 am-5:40 pm

2 stops24h 25m

Windhoek Hosea Kutako Intl

Sun 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,307

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Wed 3/11

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

Sun 3/15

2:30 pm-8:40 am

2 stops25h 10m

$1,327

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Thu 4/23

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

Thu 5/7

2:30 pm-8:15 am

2 stops24h 45m

$1,375

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 3/27

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

$1,397

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 1/24

1:00 pm-1:20 pm

2 stops40h 20m

Windhoek Hosea Kutako Intl

Sun 2/8

2:30 pm-7:40 am

2 stops25h 10m

$1,566

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Wed 3/11

2:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

Sun 3/15

2:30 pm-8:35 am

2 stops49h 05m

$1,572

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Fri 5/29

8:50 pm-1:35 pm

3 stops33h 45m

$2,353

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sun 5/31

6:00 am-8:10 am

3 stops43h 10m

$3,285

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

Sat 5/30

10:15 am-1:20 pm

1 stop20h 05m

$3,751

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 14 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 December 26, 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

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Alternative routes for Chicago to Windhoek

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