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Windhoek

$750+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ERS
fev 25 — mar 41
qua 2/25
qua 3/4
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 janeiro 26, 2026.

This Ethiopian Air deal was found by Cheapflights users on 1/25. 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 Ethiopian Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 3/1210:15 am
ORD
-
WDH
1 stop20h 05m
Ethiopian Air
sex 3/272:30 pm
WDH
-
ORD
2 stops25h 10m
Ethiopian Air
Deal found 1/25$1,235
This Ethiopian Air deal was found by Cheapflights users on 1/25. 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 Ethiopian Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 3/1910:15 am
ORD
-
WDH
1 stop20h 05m
Ethiopian Air
qua 4/12:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 1/25$1,240
This oojo deal was found by Cheapflights users on 1/25. 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.
qui 3/2610:15 am
ORD
-
WDH
1 stop20h 05m
Ethiopian Air
dom 4/52:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 1/25$1,245
This Gurufare deal was found by Cheapflights users on 1/25. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 3/1110:15 am
ORD
-
WDH
2 stops24h 25m
Multiple Airlines
qua 3/182:30 pm
WDH
-
ORD
2 stops25h 10m
Multiple Airlines
Deal found 1/25$1,314
This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 3/1210:15 am
ORD
-
WDH
2 stops26h 30m
Multiple Airlines
sex 3/272:30 pm
WDH
-
ORD
2 stops25h 10m
Multiple Airlines
Deal found 1/25$1,364
This Ovago deal was found by Cheapflights users on 1/23. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 3/2610:15 am
ORD
-
WDH
2 stops26h 30m
Multiple Airlines
dom 4/52:30 pm
WDH
-
ORD
2 stops24h 45m
Multiple Airlines
Deal found 1/23$1,380
This oojo deal was found by Cheapflights users on 1/26. 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.
qui 3/51:10 pm
ORD
-
WDH
2 stops40h 10m
Etihad Airways
seg 3/92:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 1/26$1,421
This Ethiopian Air deal was found by Cheapflights users on 1/25. 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 Ethiopian Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 5/2310:15 am
ORD
-
WDH
1 stop20h 05m
Ethiopian Air
qua 6/32:30 pm
WDH
-
ORD
2 stops24h 45m
Ethiopian Air
Deal found 1/25$1,475
This Gurufare deal was found by Cheapflights users on 1/25. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 9/310:15 am
ORD
-
WDH
2 stops26h 30m
Multiple Airlines
qua 9/92:30 pm
WDH
-
ORD
2 stops24h 45m
Multiple Airlines
Deal found 1/25$1,494
This Etihad Airways deal was found by Cheapflights users on 1/23. 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.
qua 3/41:10 pm
ORD
-
WDH
2 stops40h 10m
Etihad Airways
dom 3/82:30 pm
WDH
-
ORD
2 stops49h 05m
Etihad Airways
Deal found 1/23$1,508

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 janeiro 26, 2026.

Round-trip from

$1,235
(Ethiopian Air)

One-way from

$750
(Kiwi.com)
From Chicago (CHI) to Windhoek
Search Deals
One-way flight 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 janeiro 26, 2026.
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

qui 3/19

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

qua 4/1

2:30 pm-8:15 am

2 stops24h 45m

$1,240

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qua 4/15

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

qua 4/29

2:30 pm-8:15 am

2 stops24h 45m

$1,245

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qua 3/11

10:15 am-5:40 pm

2 stops24h 25m

Windhoek Hosea Kutako Intl

qua 3/18

2:30 pm-8:40 am

2 stops25h 10m

$1,314

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qui 3/12

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

sex 3/27

2:30 pm-8:40 am

2 stops25h 10m

$1,364

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qui 3/26

10:15 am-7:45 pm

2 stops26h 30m

Windhoek Hosea Kutako Intl

dom 4/5

2:30 pm-8:15 am

2 stops24h 45m

$1,380

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

sáb 5/23

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

qua 6/3

2:30 pm-8:15 am

2 stops24h 45m

$1,475

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qua 3/4

1:10 pm-1:20 pm

2 stops40h 10m

Windhoek Hosea Kutako Intl

dom 3/8

2:30 pm-8:35 am

2 stops49h 05m

$1,508

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

qui 3/26

10:15 am-1:20 pm

1 stop20h 05m

Windhoek Hosea Kutako Intl

dom 4/5

2:30 pm-2:27 pm

3 stops30h 57m

$1,515

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

seg 5/4

6:31 am-9:10 am

3 stops43h 39m

$750

ChicagoWindhoek

ORD - WDH

ORDWDH

Chicago O'Hare Intl

dom 3/8

12:05 pm-1:05 pm

3 stops42h 00m

$758

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 19 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
No data available for this route at this time. Please check back soon.

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

See prices for flight routes from nearby airports that may be better suited for you.
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